Ancient History & Civilisation




ON AN AUTUMN MORNING IN 334 B.C., Alexander, king of Macedon, looked down from a hillside and surveyed his prize. Below, in a natural theater, lay the great city of Halicarnassus, with the blue sea sparkling beyond it. The city was Persia’s main naval base on Anatolia’s Aegean coast, and it had fallen to Alexander’s army after a long siege.

But the Persians didn’t go before putting up a stiff fight, and they left in good order one morning after burning down half the town the night before. Worse still for Alexander, the Persians didn’t precisely leave. They withdrew from most of the city but kept the two fortified citadels (one a hill, one an island) that flanked the harbor. Halicarnassus was a Persian naval base before Alexander’s siege and it remained a Persian naval base afterward.

And so, as Alexander’s men marched into Halicarnassus, they could watch Persian warships sail serenely in and out of town as if the battle had never happened. In one of those ships sat the enemy commander, the chief strategist of the war that was not going as Alexander had planned—Memnon of Rhodes.

About a hundred years later and 3,500 miles away, on a spring day in 217 B.C., another commander’s war plan began to come unhinged. On that day two fleets, one Carthaginian and the other Roman, met in battle just off the northeast coast of Spain. They were near the delta of the Ebro River. The commanders represented the two greatest military families of the war: Hasdrubal, Hannibal’s brother, led the Carthaginians, and Gnaeus Cornelius Scipio, uncle of the later Scipio Africanus, led the Romans.

The Carthaginians outnumbered the enemy forty ships to thirty-five, and they had a land army to support them; the Romans had only the marines aboard ship. But the Romans were much hungrier for a win. Knowing that their own men held the shore, the Carthaginians gave up practically as soon as the enemy drew blood. Hasdrubal probably watched in shame as they ran their ships aground on the beach and fled. The Romans dared to row in close and towed off twenty-five of the enemy’s ships—nearly two-thirds of Hasdrubal’s flotilla.

It wasn’t a decisive operation, and Carthage still had command of Spain. But it was an ominous sign of a growing threat in Hannibal’s rear. Hannibal had trusted his brother Hasdrubal to hold Carthage’s Spanish base while he defeated Rome in Italy. If Hasdrubal failed, if he lost control of Spain to Rome, then Hannibal’s entire war plan might come tumbling down.

A little more than 150 years later and eight hundred miles to the east, in the gathering darkness of a winter evening in southern Italy, disappointment struck again. Julius Caesar’s men stood on a quay and faced the sight of an enemy navy that had escaped from under their noses. Two weeks earlier, Pompey and 27,000 soldiers had arrived in the fortified port city of Brundisium, where a fleet awaited them. He planned to sail his troops across the Adriatic Sea to northern Greece, where he would build a new and bigger army, aided by his many allies in the East. Since he controlled the sea, Pompey knew that he could return the following year and fight from a position of strength.

Caesar planned to stop him. He had one part of his army lay siege to Brundisium and the other part try to close off the harbor, outside its walls, by building a mole across it. But Pompey fought back.

In the end, when Caesar’s troops broke into Brundisium, there was nothing left of Pompey’s forces except two ships stuck in Caesar’s breakwater. All the rest had escaped. Pompey had succeeded in breaking out of his great opponent’s trap.

“No battle plan survives contact with the enemy.” When he wrote his famous maxim, German General Helmuth von Moltke (1800–1891) was thinking of the Franco-Prussian War of 1870–71 but he might have had our three commanders in mind. Soon after going to war, each of them had to rewrite his plans.

Alexander discovered just how much harm the Persian fleet could do him under the command of a great admiral. Hannibal faced an enemy who sidestepped his attack in Italy but threatened his rear in Spain. Caesar met an enemy who rebuffed him and regrouped for a counterattack. All three men faced frustration.

Military thinkers, ancient and modern, would certainly sympathize. Most generals and kings, wrote Polybius, think only about success; they “do not envision the consequences of misfortune or consider at all how they should behave and what they should do in the event of disaster, although . . . [it] takes great foresight.”

The American admiral James Stockdale put it succinctly: “The challenge of education is not to prepare a person for success, but to prepare him for failure.”

How prepared for failure were Alexander, Hannibal, and Caesar? Did they adjust with agility?


After smashing the Persians at the Granicus, Alexander was free to get down to business. That business was decidedly not marching eastward against Darius. Not yet. Alexander’s immediate need was to get food for his men and money to pay them. That in turn meant winning over the cities of western Anatolia, most of which were Greek. With his army to remind them who was in charge Alexander offered carrots and sticks. To popular acclaim, he replaced oligarchies with democracies. This was less idealism than pragmatism on Alexander’s part. Aristotle had taught him that democracies were more stable than oligarchies. In western Anatolia, where Persia had long supported oligarchy, democrats were Macedon’s natural allies. He also imposed taxes, nicely relabeled as “contributions.” The locals cheered for democracy and accepted taxation with the resignation of people who were used to conquerors. Alexander claimed he had come to “liberate” these cities, but they knew better than to take him at face value.

Before turning eastward, Alexander had to control the west. So far, he had won a battle but not the war. The Persian navy commanded the Aegean; a new Persian army could march westward in massive numbers. Alexander’s forces were still relatively small and poor. He would soon need reinforcements to replace men lost in battle or to sickness or left behind to garrison conquered territory.

There would still be dozens of twists and turns in the conflict. Each resulted from a Persian counterattack; each tested Alexander. The three most important are Memnon’s naval offensive, the battle of Issus, and the siege of Tyre.

Wooden Walls: Persia’s First Counterattack

Four hundred Persian galleys—“wooden walls,” as a Greek once called warships—dominated the eastern Mediterranean. With its naval superiority, Persia could cut the enemy’s communications, land in Greece, and raise a revolt against Macedon. That would force Alexander to return home or risk losing Macedon, his native land and the source of future reinforcements. Alexander could solve the problem by beating the Persian fleet, but how could he polish off a much better navy?

By doing it on land! Alexander claimed that by using his army and siege train to capture Persia’s seaports, he could deny the enemy the use of its fleet. The Persians weren’t buying, though.

Memnon of Rhodes was both the brains and the muscle behind Persia’s naval policy. His strategic audacity and tactical toughness equaled Alexander’s, but unlike Alexander, Memnon was not king; Darius was. As a foreigner and one linked with a rival Persian family, Memnon never won Darius’s complete trust. In fact, Memnon was forced to send his wife and children to Darius as hostages in order to hold his command. But when Memnon fought, he made Alexander sweat.

The first round took place in summer 334 at Miletus, a key port on the Aegean coast of Anatolia. The Persian navy didn’t perform as well as some hoped, and we might wonder whether Memnon was there, as one source—but only one source—states. In any case, the mere presence of the Persian fleet spooked Alexander, as it turned out. It happened as follows:

Miletus sat on a narrow peninsula in the Gulf of Latmos, protected by the strategic island of Lade nearby. A pro-Persian party governed the city with the support of a garrison of Greek mercenaries. As Alexander’s army approached by land, the pro-Persians got the good news that Persia’s fleet of four hundred ships was on its way. But Alexander’s navy of 160 ships reached Miletus first. Whoever controlled the island of Lade controlled access to Miletus, so the Macedonians landed at Lade and garrisoned it with five hundred men. The Persians were compelled to anchor across the Gulf of Latmos, about three miles away. (Ancient navies always needed a friendly shore to find food and water and to anchor at night.)

Meanwhile, the Macedonians debated strategy. Alexander’s chief subordinate was Parmenio, a much older man, a political power in his own right, and Philip’s greatest general. Alexander respected Parmenio but distrusted him. Parmenio now advised a naval battle but Alexander refused to risk it against an enemy that was superior both in numbers and experience. He worried that his “allies” back in Greece were so restive that they would rise in revolt at the mere news of a Macedonian defeat at sea.

Instead of fighting a naval battle, Alexander used his fleet as a shield. His ships held the Persian fleet at a distance while, on land, his army laid siege to Miletus. His engines quickly broke through the walls and took the city. Some of the enemy garrison tried to swim to safety but Alexander’s navy captured them. Still, Alexander feared that the Persian fleet would come back and defeat his navy, so he sent a unit of cavalrymen on a long march around the Gulf to the Persians’ anchorage, where they destroyed the enemies’ shore parties. Now the Persians had to sail off to the island of Samos for supplies, an additional five miles away. The battle for Miletus was effectively over.

Alexander’s fleet had played a role in the victory, but he was not impressed. It was his army that captured the city and his cavalry that drove the Persian fleet away. Besides, Alexander never entirely trusted the sailors, who came from his less-than-loyal Greek allies. He considered the navy a bad bargain, given the expense of paying the sailors and keeping the ships in trim. So Alexander made a bold decision: he sent most of the fleet home.

Alexander dismissed 140 ships, keeping only 20 Athenian vessels to carry siege equipment; incidentally, the several thousand Athenian sailors were virtual hostages. It was a major blunder. As the Miletus campaign showed, Alexander’s fleet was of limited use but it was not useless. Worse, no navy meant no defense against a Persian thrust across the Aegean. If the Persians chose to strike, Alexander had left them a wide-open target.

Alexander took risks but usually with carefully planned forethought. Dismissing his navy was different. Suddenly Alexander gave up one of the foundations of his strategy and replaced it with an untested theory: that it was possible to defeat sea power on land. This decision was a mistake. As a Macedonian, Alexander came from a nation of landlubbers. Maybe he just plain distrusted ships.

The Persian fleet now sailed south to Halicarnassus, another major naval base on the Aegean coast. Alexander fought hard—on land—to take the city, while Memnon fought even harder to organize its defense. At Halicarnassus, unlike at Miletus, the Persians had control of the sea, which gave Memnon’s forces mobility and access to supplies.

In the end, Halicarnassus gave Alexander a tactical victory but a strategic defeat. Alexander forced Memnon to withdraw from the town—but not from the fortified port, which remained in Persian hands. During the siege Memnon inflicted high casualties on the Macedonians. He also defeated Alexander’s attack on the neighboring port city of Myndus by sending naval reinforcements to the Persian garrison there. Memnon evacuated most of his soldiers from Halicarnassus to the nearby island of Cos. But the Persians retained a naval presence on Anatolia’s Aegean coast: in their garrison at Halicarnassus, at Myndus, and in two port cities farther south, Cnidus and Caunus, neither of which was easy to attack by land. In short, Alexander did not drive the Persian fleet from all bases on the Anatolian coast.

It was the end of the year 334 B.C. and it marked Memnon’s moment. The veteran warrior finally convinced Darius to let him launch a major naval offensive, made up of three hundred ships and fifteen thousand mercenary soldiers. Since Alexander had virtually no navy, this force could sweep across the Aegean Sea and bring the war to Greece. It was what Churchill would later call a “soft underbelly” strategy: attacking the enemy not where he was strong and protected, but where he was weak.

Memnon began his naval offensive in spring 333. Right away he took several important Aegean islands allied to Alexander, including Chios and all of Lesbos except the big city of Mytilene, which fell after a siege. According to one source, the Persians also retook Miletus.

Alexander was concerned. His gamble of dissolving his navy now seemed foolhardy. It was time to revise his plans. He sent a huge sum to Greece in order to raise a new fleet but it would not be ready for months.

Then he continued southward and eastward, to Anatolia’s Mediterranean coast, where he could deny Persia access to an important source of sailors and ship timber as well as capture additional ports. Deprived of these ports, Persian ships found it much riskier to travel between the Aegean and Persia’s major naval bases in Phoenicia (modern Lebanon). Alexander did another thing as well: he raised money from the rich cities in southern Anatolia. If they refused to be “liberated,” he marched on them.

All the while, Alexander kept his eye on Memnon and the Aegean. After leaving Halicarnassus, he divided his forces. He kept half of his army with him and sent the rest, under Parmenio, to the city of Gordium in north-central Anatolia. Gordium was the perfect pivot point. From there, Parmenio could march back to Macedonia, if Memnon attacked, or send reinforcements to Alexander, if needed.

Alexander cultivated an image of action. But except for his dismissal of his fleet, his overall policy during his first year in Anatolia was slow and deliberate. The myth was different. Nothing symbolizes it better than an event at Gordium in spring 333. There, Alexander “fulfilled” a prophecy that he would conquer the Persian empire by untying an immensely intricate knot: he “untied” the knot by cutting it with his sword. The man who cut the Gordian knot had no patience for the slow and deliberate way of doing things. He was a dashing young hero forging always forward. But that was just the myth.

In fact, Alexander was cautious enough to know when to call off an attack, even if it allowed his enemies to boast that they had beaten the mighty Alexander. Myndus, the port near Halicarnassus, was just one example of his holding back; he did the same with the cities of Termessus and Syllium, both located just inland from Anatolia’s Mediterranean coast. A good commander knows when to retreat, and Alexander did. He had bigger problems, after all.

For a moment in spring 333, it looked as if Alexander’s early victories might fall victim to Persia’s counterattack. But Divine Providence smiled: in June, Memnon died of an illness. His nephew, Pharnabazus, and his deputy, Autophradates, continued the campaign, but they were lesser men. They couldn’t match Memnon’s skill at war, his knowledge of Macedon, or his clout with Darius.

Memnon’s death was a turning point. Had he lived, he might have lit a fire in Greece. He would probably have conquered other strategic Greek islands and landed on the mainland with fifteen thousand Greek mercenaries. Important city-states were ready to join the Persians in the fight, especially Sparta, which had never accepted Macedonian rule. In 331, these states actually did rebel against Macedon, but it was too late. By then, Alexander had acquired so much loot that he could finance a new mercenary army to add to the small force that he had left behind to defend Macedon. They crushed the rebels. But a rebellion in 333 would have forced Alexander to march back home to defend Macedon. That would not have been easy if Memnon had blockaded the Hellespont.

In May 333 it seemed that Alexander’s policy had failed: he could not stop Persia’s naval offensive without a navy of his own. But in June, Memnon’s death saved him.

Darius ended the naval offensive. He decided to withdraw most of the mercenaries from the fleet and transfer them to the mainland. Had Memnon survived, he might have persuaded the Persian king to reconsider. As it was, Darius decided to take resources from the war at sea, where the enemy was weak, and transfer them to a battle on land, where the enemy was strong.

The Battle of Issus: Persia’s Second Counterattack

It is the most famous face-off in the history of art. A mosaic from Pompeii shows the scene. Alexander the Great, spear in hand, charges on horseback against Darius of Persia. Three Persian cavalrymen and a row of pikes are all that come between the two warrior-kings. Driving ever forward, with his horsemen riding beside him, Alexander is poised to kill Darius. The Persian king is in danger and he knows it: he stands wide-eyed on his chariot, facing Alexander. But Darius’s charioteer is ready: having turned the horses away from Alexander, he pulls the reins and cracks a whip to spur a rapid escape.

Frozen in time, the moment captures the climax of a dramatic clash of kings: the battle of Issus, on or around November 1, 333 B.C. On an autumn afternoon, the Macedonian and Persian armies fought over the fate of empire. The Macedonians were a winning and experienced force but the Persians had strengths too and they outnumbered the Macedonians two to one.

Issus is known as a clash of kings that highlighted Alexander’s heroism. That’s no accident. Like the Kennedys or Princess Diana, Alexander had a knack for public relations and he highlighted his valor. But, in truth, Issus demanded other qualities; not Alexander’s heroism so much as his coolness, steadiness, and caution won the battle.

The die was cast for combat by spring 333 when Darius gathered an army. He knew, of course, of the risk of fighting the Macedonians in pitched battle. But Darius’s own army was no pushover. The Persian king was aware that Alexander was heading south and east. In fact, by summer 333, Alexander reached Cilicia, the fertile and wealthy plain on Turkey’s southern coast and the gateway to Syria. In the months before, he had rejoined Parmenio and the rest of the army at Gordium, where he received four thousand to six thousand reinforcements, mostly from Macedonia.

Not wanting to risk Alexander’s entry into the heart of the empire in Mesopotamia (modern Iraq), Darius chose to fight him in Syria. The Persian had to respond quickly, which meant that he had no time to gather all of the empire’s far-flung forces. In particular, Darius would have to do without the great horsemen of Central Asia. But he would gather a strong army, even so.

By September, Darius and his soldiers were ready to march. October 333 saw them camped on the plains of Syria, with the tall Amanus Mountains lying to the west and Cilicia—and the Macedonians—beyond. Alexander had surely heard of Darius’s plans, but he was shocked to discover how close the enemy was: in Syria, less than a week’s march away.

Both armies wanted to fight, but in entirely different places. The Persians wanted the contest on the wide plains of Syria, where they could spread out and make use of their superior numbers. Alexander hoped to fight in a narrow space between the mountains and the sea, where the Persians could not deploy their army comfortably. There was suitable terrain around Issus, a coastal city at the head of the Gulf of Issus (today, Turkey’s Gulf of Iskenderun). There, a coastal strip, only several miles wide, stretches from the Amanus Mountains to the Mediterranean. As it turned out, Alexander got to fight where he wanted but not as he wanted.

It happened like this: Alexander, encamped in the west, refused to take the bait and cross the mountains to head for Syria and the Persians. So, either out of impatience or because his army was running out of food, Darius decided to cross the mountains himself and fight Alexander in Cilicia, where the broad coastal plains would make an acceptable substitute for his preferred battlefield in Syria. Darius entered Cilicia via the Amanus Gates (Turkey’s Bahçe Pass). But Alexander had already left. He was marching south past Issus and along the narrow Mediterranean coast toward Syria.

Darius now followed, which was good for Alexander, except that Alexander expected Darius to march toward him from the south, after crossing the Amanus range via the Syrian Gates (Turkey’s Belen Pass).

But Darius surprised Alexander by coming from the north, via the Amanus Gates. When Darius reached the Mediterranean at Issus, he found himself in Alexander’s rear, cutting off the Macedonians from their supplies. What a shock for Alexander! A lesser general would have been nonplussed by Darius’s unexpected arrival behind him, but Alexander stayed calm. He was a cavalryman, after all, and cavalrymen are used to operating far from their home base. The crisis brought out the best in the Macedonian king.

It was evening. After his men ate, Alexander marched the entire army toward the Persians, covering a distance of about ten miles. After camping in a narrow pass, at dawn the next morning they began marching about another ten miles toward the Persians and then fanning out into battle order.

Without breaking a sweat, Alexander turned his army around rapidly and deployed it for battle. He displayed agility and audacity. Above all, he displayed strategic intuition. He was able to assess the situation quickly and come up with the right solution.

Darius should have tried to draw Alexander back northward, into the plain. But surprise is a force multiplier that dramatically increases an army’s effectiveness, and maybe the Persians thought they had caught Alexander off guard. Or perhaps, as one source says, it was too dangerous to retreat with Alexander ready for battle. And so, the Persians stood and fought.

The two forces met on the steep-banked Pinarus River, which ran from the winding foothills of the Amanus Mountains to the Mediterranean, where it reached a level beach. (It is almost certainly to be identified with today’s Payas Çay.) Here, according to the ancient sources, the plain was about one-and-a-half miles wide. The game of moves and misdirection had ended, to Alexander’s distinct advantage. Darius had wanted to fight on the plain and Alexander to fight in the narrows; Alexander had won.

It is clear that Alexander was greatly outnumbered. An educated guess is that he had nearly 30,000 infantry and about 5,000 cavalry. Darius’s forces were 65,000 infantry, including 15,000 Greek mercenaries and 15,000 cavalry. The mercenaries were first rate, but the other Persian infantrymen were not.

Alexander positioned his troops on the south bank of the Pinarus. He arranged them in what would become his classic battle order. The Macedonian phalanx stood in the center of the line, to tie down the Greek mercenaries opposite them. On the left wing, allied cavalry and light-armed troops took a defensive stance, under the command of the veteran general Parmenio. The right wing was the Macedonians’ striking arm, spearheaded by the Companion Cavalry and led by Alexander himself. Their task was to look for an opening in the enemy line and pour through it.

Alexander followed a simple strategy at Issus: decapitation. By tradition, the Persian king stood at or near the center of his battle line, behind a protective infantry force. At Issus, Darius stood closer to his left flank. Alexander aimed straight for Darius, hoping to overpower his guards—the weaker Persian infantry, not the Greek mercenaries—and force the Persian king to run for his life. He figured that when Darius’s army heard that their leader had fled in fear, they would give up—even if they happened to be winning on their part of the battlefield. Alexander’s greatest hope was to kill Darius; that would shake the Persian political system and might even cause its collapse.

Darius took up a position on the steep, northern bank of the Pinarus. It was good defensive ground, but he needed to go on the offensive. That was a job for the cavalry; the infantry would absorb the enemy’s attack. The Persians posted their cavalry on the wings and their infantry in the center. Ideally, they hoped to fight on a wide battlefield, but unfortunately for Darius, Issus was narrow. Had he fought on the plain, Darius would have enveloped the Macedonian army with his superior numbers of cavalry. But at Issus, the Mediterranean and the mountains protected the Macedonian flanks. Darius needed a new plan.

He got one, proving himself a quick and creative thinker. Darius recognized two weaknesses in the Macedonian army: the phalanx (in the Macedonian center) and the allied cavalry (on the Macedonian left wing). He was confident that his Greek mercenary phalanx could hold the Macedonian phalanx, but he wasn’t sure that his cavalry on the Persian right wing could break through the enemy cavalry opposite it. So he added power to his punch by transferring most of the cavalry on the Persian left wing to the Persian right wing, which he hoped would help the Persians to break through the enemy line near the sea. Unfortunately, that left the Persians’ left wing, which stood near the foothills of the mountains, vulnerable. Darius tried to defend that wing by sending light-armed troops, armed with missiles, such as javelins and arrows, into the foothills, where they could circle around and take the enemy in the rear.

Both moves looked promising, but Alexander parried them. He too proved up to the challenge of readjusting under pressure. He placed archers and javelin-men in the foothills on his right to deflect Darius’s thrust. Then, just before the battle began, Alexander moved the best of his allied cavalry, the Thessalians, to his left wing—and he did so in secret, by moving them behind his lines. Once again, Alexander displayed his strategic intuition.

It probably took all morning to get the armies into position; the battle began in the afternoon. The two armies were already in sight of each other but not yet in javelin range. The sources report that Alexander rode ahead of his front standards and called out his commanders by name to encourage them. No doubt the Persians did something similar. Then came two final moves to inspire the men. In both armies the trumpeters signaled the attack and the men shouted their battle cries. The roar echoed off the thickly wooded mountains.

The battle confounded expectations. In the center, Darius’s Greek mercenaries not only held off the Macedonian phalanx, but they found gaps in it and made the Macedonians pay in blood. On the Macedonian left, Parmenio led a tough defense that kept the Persian cavalry from advancing. Darius’s blow was stopped. Meanwhile, the Macedonians unleashed their own strike from their right wing.

Alexander led his Companion Cavalry across the Pinarus, up the opposite bank, and into the Persian infantry. The sources disagree about whether they charged across or simply cantered. Once they reached the Persians, the Companion Cavalry cut through them until Alexander was fighting in sight of Darius. Now there took place the famous confrontation of the two kings with which this section began. After realizing that his position was hopeless, Darius turned and fled. He was not a coward but a realist. He understood that he had lost a battle but could still win the war—as long as he survived.

Alexander, meanwhile, passed another test of his judgment. Despite the temptation to ride after Darius, he was mature enough to put first things first: he now turned toward his center to help his phalanx. That turned the tide, and the Macedonians pushed the Greek mercenaries back. Alexander received a minor thigh wound in the fighting. Meanwhile, Parmenio and the Thessalians on the Macedonian left launched a counterdrive against the Persian cavalry. Whether because of that thrust or the news of Darius’s flight, the Persians turned and galloped off toward safety. But their own infantry blocked the way, and many men were trampled to death.

Macedonian casualties were higher at Issus than at the Granicus. The sources, who probably underestimate, report five hundred Macedonian deaths and four thousand wounded. Persian losses were much, much higher: an army that tries to run away over rugged terrain is bound to suffer. No reliable Persian casualty figures exist.

Issus turned out as it did for three reasons: prebattle maneuvers, the skill of the Macedonian army, and the good judgment of Alexander. No fool, Alexander knew how much he relied on his generals. Without the heroic defense on the left wing by Parmenio, for example, the Persians might have taken Alexander in the rear and the result would have been a very different story. The Persians were far from incompetent. They fought well but the Macedonians outclassed them.

Darius had organizational and tactical skills, and he was quick on his feet. But he lacked Alexander’s self-confidence and single-mindedness, and Alexander’s gifts as a battlefield commander. Besides, compared with Macedon’s military machine, the Persian army was brittle and inexperienced.

Issus was a great victory for Alexander but it didn’t decide the war. Darius survived, as did part of his army. He still controlled most of a vast empire, with huge military and financial resources at his disposal, including the Mediterranean’s preeminent fleet.

In fact, Alexander might have been frustrated with the battle’s outcome. He had come close to killing the one man who, more than any army, stood between him and control of an empire. Now, Alexander would have to fight him again or negotiate with him.

But the contest would not continue at the same level as before. Alexander had improved his position enormously. As an added bonus to battlefield victory, he captured money and very important people. Persian kings brought their family to the battlefield, probably as a sign of confidence. Forced to run for his life, Darius left behind his mother, principal wife, daughters and son, all of whom fell into Alexander’s hands. They were now hostages. Alexander also sent Parmenio rushing to Damascus, where he captured more than three thousand talents (about 175,000 pounds) of gold and silver as well as additional hostages. One of the hostages, Memnon’s widow, Barsine, eventually became Alexander’s mistress.

Walls and Words: Persia’s Third Counterattack

Issus dealt Darius a bitter blow but not a fatal defeat. He decided to reopen the war at sea in the Aegean and try once again to raise a revolt in Greece. All would not be quiet on the western front—not if Darius could help it.

Alexander knew it, and so he made haste to seize the seaports of Phoenicia. These cities had always been Persia’s staunchest naval allies. They had often served in the past as naval bases for Persian offensives against Greece. Now, all of them surrendered to the advancing Macedonians—all except Tyre, which tried to maintain its neutrality. Perhaps the Tyrians were betting on a Persian revival. Alexander could not allow Tyre to serve as a symbol of resistance and a potential Persian naval base. So he embarked on a massive siege.

Located on an island off the mainland, Tyre was a natural fortress. It was not about to give in without a fight. In fact, Tyre stood firm for eight months, from about January to about August 332, until it finally fell. To take the city, the Macedonians built a huge mole from the mainland and brought up siege engines. The battle was decided at sea, however. When the other Phoenician cities surrendered to Alexander, their navies were off fighting on the side of the Persians. Eventually, they switched sides and returned to Phoenicia to fight against Tyre. That sealed the city’s fate. The Macedonians broke into Tyre, killed about six thousand to eight thousand Tyrians, and sold about thirty thousand into slavery. Another fifteen thousand Tyrians were saved by relief ships from other, still-friendly cities. As at Thebes, Alexander showed just how brutal he could be.

By laying siege to Tyre, Alexander once again passed the test of Persia’s counterattacks. Bloody, frustrating, expensive, and time-consuming, the siege of Tyre was necessary. The Macedonian knew to protect his flank at sea before turning eastward toward Persia. At Tyre, Alexander’s strategy of winning a naval battle on land worked, thanks to the Phoenician navy.

But if Alexander had had a navy of his own, the siege might not have taken eight months. As it was, he was dependent on the Phoenicians for ships, and it took time to win them over.

Meanwhile, Persia was fighting in two other theaters in the west. The fleet, led by Memnon’s successor Pharnabazus, took or recaptured several strategic Greek islands including Lesbos (in particular, its main city of Mytilene), Chios, Tenedos, Siphnos, Cos, and parts of Crete as well as the Anatolian mainland cities of Miletus and Halicarnassus. The Persian army, back on its feet after Issus, tried to fight its way into Lydia, a rich and strategic province in central western Anatolia. In a bold move, the Persians struck in winter, usually the off-season for warfare. Taking Lydia would have given the Persians a base in the hinterland to support garrisons in Miletus and—slightly farther afield—Halicarnassus.

The Lydian offensive was a strategic stroke by Persia, but the Macedonians responded by displaying the depth of their military talent. Antigonus “the One-Eyed,” a veteran commander of Philip, nicknamed for his war wound, defeated the Persians “in three battles in different regions”—unfortunately, no further details survive. But the result was clear: Lydia would not revert to Persian rule. No wonder that by spring 332, various contingents of the Persian fleet defected to Alexander at Tyre.

Looking back at the war between the Granicus and the fall of Tyre, we can see Alexander’s good moves, his mistakes, and his luck. His brilliance as a battlefield commander won victory at Issus. He was smart enough to chip away at the enemy’s naval bases, but that wasn’t enough. Alexander courted disaster by disbanding his fleet. If Memnon had lived or if Darius had stuck to the naval offensive and avoided battle, the Persians might have stirred up revolt in Greece and forced Alexander back home. Ultimately, Alexander’s response to Persia’s counterattack was to trust that the enemy would stumble. The gamble paid off, and Persia lost the war for the west. But a wise commander does not give the initiative to the enemy, a lesson that Alexander would eventually learn to his cost.

Having temporarily run out of military options, Darius turned to diplomacy. He had to try negotiation, in any case, because his family was being held hostage. Darius made a series of offers to Alexander: in exchange for an end to the war and the return of the great king’s family, Darius offered Alexander a large ransom, a Persian royal princess as his bride, and the western Persian empire. Darius first defined this territory rather stingily as western and central Anatolia and then, more realistically, as everything between the Mediterranean and the Euphrates rivers (in today’s Iraq). According to the sources, Alexander’s senior general, Parmenio, responded positively, saying, “I would accept if I were you, Alexander.” The king is supposed to have replied, “So would I, if I were Parmenio.”

Historians have doubted this anecdote, since in later years Alexander’s propagandists poisoned Parmenio’s reputation. But whether the anecdote is true or not, Parmenio offered pretty good advice. Any advance eastward would be risky. Darius retained huge resources. He could organize a new and bigger army than the one at Issus. Worse still, he might refuse to challenge Alexander in battle. If Darius finally accepted Memnon’s strategy of a scorched-earth policy and added sudden, unpredictable cavalry raids, he might bog down the Macedonian army on any advance they made to the east.

And what if the Macedonians won? While we don’t know what was in Parmenio’s mind, it’s easy to imagine him pursuing a different grand strategy from Alexander’s. As Parmenio perhaps saw it, the purpose of the war was to add new territory and wealth to Macedon, but Macedon would remain the center of gravity; it would govern the new kingdom. If Alexander continued his conquests, however, the tables would be turned, and Western Asia, with its huge mass, would outweigh little Macedon. And then, who would be governing whom? And how stable would the vast new empire be? Could Alexander and the next king of Macedon maintain control of it, or would it break up into separate parts?

If Parmenio expressed these doubts, Alexander might have replied as follows: continuing the war was risky but so was accepting Darius’s offer. Peace would give Darius breathing space to regroup and attack again—at a time of his choosing. Better for Alexander to continue the war now and finish Darius off, a task that Macedon’s brilliant, veteran army had a real chance of completing. Besides, to put a stop to unrest in Greece, Alexander must conquer Persia’s two capital cities, Susa and Persepolis, because otherwise he could not claim to have fulfilled his promise of avenging Xerxes’ conquest of Athens in 480 B.C. Besides, the Persian treasury—the largest in the world—would make Alexander the richest man in the world, and the least vulnerable.

But another, unspoken issue might also have loomed large in Parmenio’s mind, a matter of domestic politics and constitutional considerations. The king of Macedon had never been an absolute monarch; the Great King was. Parmenio and his fellow Macedonian aristocrats could hold their own against the king of Macedon, but if Alexander became the king of Asia, he would dwarf them.

Alexander responded to Darius’s offer by demanding the Persian recognize that, he, Alexander, was now the “king of Asia.” The term was vague but it clearly meant something grand, verging on absolute power. And that, it seems, is what worried Parmenio.

The year after conquering Tyre, from 332 into 331 B.C., Alexander would proceed toward Egypt, taking Gaza by force and Judaea by diplomacy. He then proceeded to a bloodless conquest of the rich and fabled kingdom of the Nile, where he had himself crowned as pharaoh. All the time, though, he was looking eastward toward the heart of the Persian empire in Mesopotamia and Iran.

Alexander now hoped that Darius would challenge him in battle. The alternative, a combination of scorched-earth policy and ambushes, made the Macedonians shudder. Alexander didn’t have to worry; in 331, he would get his fight. But winning it would take a supreme effort.


As soon as spring came to northern Italy in 217 B.C., Hannibal moved south. His plan was to win battles that would convince Rome’s allies that Carthage was now top dog, and so would lead them to defect. Stripped of its supporters, Rome would sue for peace. Or so Hannibal hoped.

Hannibal’s biggest worry was, as they said in the 1960s, what if they gave a war and nobody came? Or, more precisely, what if the Romans refused to fight a battle? What if, instead, they burned his food supplies and raided the edge of his army?

Hannibal’s other worry was whether Rome’s allies would really change sides. Unlike Alexander, who won many cities in Anatolia to his side, Hannibal had yet to find a base of supply. Without food and in a hostile country, how long would his men go on following him? What if the war in Italy turned from a glorious fight on the field of honor to a struggle against hunger and want?

A Crossing, a Trap, and a Road Not Taken

Hannibal had hard luck with crossings. The passage through the Alps in 218 B.C. nearly destroyed his army. The crossing of the Apennines from Emilia into Etruria (Tuscany) in spring 217 (perhaps in May) exacted a lesser price, but a heavy one even so. Several routes led over the Apennines into central Italy. Hannibal chose the shortest and least often used one, in order to surprise the Romans. They didn’t expect anyone to risk crossing the marshes of the Arno but Hannibal had the audacity to do just that. In 217, heavy flooding led to swampy and sometimes virtually impassable conditions, probably in the area north and west of Florence. It took four days to get through the miserable terrain.

Hannibal deployed his army so that the best troops would march first, before the tramp of tens of thousands of feet softened the ground. By the time the Celts passed through, the soil was so soggy that many drowned in the marshes. But Celtic soldiers were expendable in Hannibal’s mind. So were the pack animals, because he expected to get plenty more of them in the south; most of them died on the trek too. All but one of the few surviving elephants now died as well. So be it, Hannibal might have said. But he couldn’t have expected what happened next.

Hannibal came down with an eye infection that he refused to treat during the difficult crossing of the marshes, which left his right eye sightless or virtually sightless (the sources disagree). The damage was permanent.

As a soldier, Hannibal does not seem to have suffered much from the handicap. As a leader of men, he might even have benefited from it. His Celtic troops, like many ancient peoples, believed in the symbolic power of a single eye. The Celts worshiped as one of their chief gods Lugus, who closed one eye when he made war magic. So as a one-eyed man, Hannibal might have seemed to “see” things even better than before his injury. The Barca “brand” had just gotten stronger.

Except for their victories in northern Italy, Hannibal’s army had little to cheer about since taking the long road from Spain. Including the Celts, they now numbered about sixty thousand men. They were all bone-tired after the trek through the Arno swamp. Some of them had also suffered through the Alps and were unaccustomed to the cold of winter in northern Italy. Malnourished, most of them suffered from scurvy, which slowly weakened them. But the rich fields of Etruria beckoned, as Hannibal surely told them. Once again, he displayed leadership in a crisis. As they crossed the Apennines, the men might have noticed the vegetation change from continental to Mediterranean: first the pines and then, as they descended into the valley, the olive trees. The sun was stronger here than in the Po Valley. Hannibal had entered some of the wealthiest and most intensely cultivated territory in the Mediterranean. Hungry predators, the Carthaginians plundered the rich countryside between Arretium (Arezzo) and Cortona.

But the Romans were nearby. His scouts told Hannibal that a Roman army was camped at Arretium, with a second one less than a week’s march away at Ariminium (Rimini) on the Adriatic coast. Each army had about 25,000 men and each was led by a consul: Gnaeus Servilius at Ariminium and Gaius Flaminius at Arretium. Flaminius, a prominent general and politician, had played a key role in conquering northern Italy a decade earlier. Now his troops carried chains for imprisoning the enemies they were confident of defeating. Knowing this, Hannibal marched his men right past Flaminius in order to lure him into battle. It worked.

On the morning of June 21, 217 B.C., Flaminius followed Hannibal along the northern shore of Lake Trasimene, a large body of water in central Italy. The Roman may have felt triumphant. He probably thought that he had Hannibal trapped between his army and Servilius’s off to the northeast. A few years earlier, Flaminius had sprung a similar trap on a Celtic force. But as he entered a narrow pass on this misty morning, it was Flaminius who walked into a snare.

The northern shore of Lake Trasimene consists of a series of valleys, each surrounded by mountains ending at the water. It is lush and green territory, heavily planted today with olives as well as grass and alfalfa for hay. Camouflaged and hilly, it was, as the historian Livy writes, a land made for ambushes. Still, it was not easy to hide sixty thousand men, and it is a tribute to Hannibal that he did. At a signal, they descended from the surrounding heights. The Romans were shocked and unprepared.

It took only about three hours for the Carthaginians to cut down the Roman army. With few of the Romans able to line up in order, it was less a battle than a massacre. Some of the Romans sought safety in the marshes that still line the lakeshore, only to be slaughtered in the water. Hannibal’s men killed fifteen thousand Roman soldiers and captured ten thousand to fifteen thousand more. Flaminius was among the fallen; one account says that a Celt got his revenge by killing and decapitating the conqueror of northern Italy. Hannibal’s army suffered only one thousand five hundred losses, mainly Celts. When the other consul, Servilius, sent his four thousand cavalry from Ariminium to reconnoiter, Hannibal dispatched a mixed force of infantry and cavalry against them, led by his brilliant lieutenant Maharbal. The Carthaginians killed or captured all of Servilius’s cavalry.

In short order, Hannibal had destroyed one of Rome’s two consular armies and left the other virtually immobilized. It was a complete and utter humiliation for the Roman army. For Hannibal, it was a stunning display of good judgment on the part of a commander.

Rome now feared the worst. The road to the capital lay open, and yet Hannibal declined to take it. Why? Rome was only eighty-five miles away, a four days’ march down the via Flaminia, a road recently built by none other than Flaminius. Rome’s garrison probably numbered no more than ten thousand men. In addition to his army, Hannibal knew that a Carthaginian fleet lay off the coast at nearby Pisae (Pisa), where he had prearranged a rendezvous. Why not attack Rome by land and cut it off by sea?

The sources hint at a debate in the Carthaginian high command on this very question. But Hannibal’s forces were simply not up to it. They still hadn’t recovered from their exertions. Ringed by a massive wall, Rome might have required a long siege. Unless Rome fell quickly, there would be time enough for Servilius’s men and the legions in Sicily and Sardinia to come to Rome’s aid. Rome still had substantial manpower resources. Hannibal had achieved a great deal with small numbers, but he needed reinforcements.

He might have looked for them in Rome’s allied cities. South of Lake Trasimene lay the cities of the Etruscans. They included many opponents of Roman rule. By marching up to their walls, Hannibal might have emboldened them to open the gates and let him in.

But, like Rome, the Etruscan towns probably seemed like too big a challenge for Hannibal’s weakened army. So, instead, he turned east and marched toward the Adriatic coast. Along the way, he acquired so much booty “that his army could not drive or carry it all off.” About two weeks after the battle at Lake Trasimene, Hannibal’s army reached the Adriatic. There, “in a country abounding in all kinds of produce,” Hannibal finally gave his men and horses the rest they needed. Hannibal’s leadership style was to drive his men hard but then reward them generously.

Hannibal now sent a message to Carthage announcing his success; amazingly, this was the first word the city received from Hannibal since he had reached Italy. They were thrilled by his success but the Carthaginians wondered when their general would go for the enemy’s jugular.

Fabius the Delayer

Faced with disaster, the Romans did what people have done throughout the ages: they elected a dictator. The Romans originated our term “dictator”; to them, he was a special public official chosen to govern in an emergency. A dictator held supreme authority but only for six months at most. A dictator’s power wasn’t quite dictatorial: it could be challenged by his second-in-command, who was called the master of the horse. The Romans hadn’t elected a dictator for two generations, but now the time had come. For their dictator, the Romans turned in July 217 to an experienced leader, an aristocrat who had been consul and had conquered the Ligurian tribes of the northwest Apennines: Quintus Fabius Maximus. The ex-consul Marcus Minucius served as Fabius’s master of the horse.

Like Memnon of Rhodes, Fabius was a general worthy of his opponent. At the age of fifty-eight, he remained vigorous; he had a veteran commander’s cunning and the strategic insight and grandeur of vision to match Hannibal’s. Unlike his predecessors, Fabius decided not to go on the offensive. Instead, he followed a policy of attrition, aimed at wearing Hannibal down. It was a scorched-earth policy, much like the one that Memnon had called for and the Persians rejected. Fabius understood that Hannibal’s strength was his army and its forte was pitched battle. Hannibal’s weakness was the need to replenish supplies and numbers of men, both of which he lacked. Rome, by contrast, enjoyed “inexhaustible supplies of provisions and men.”

Fabius refused to fight another pitched battle with Hannibal. Instead, he ordered the Romans to follow and harass the Carthaginian while cutting his army off from potential sources of food. Fabius took various steps to protect his forces, such as always camping on high ground, where he was safe from Hannibal’s cavalry, and never letting his men go out foraging, where they might face danger. At the same time, he killed or captured numerous Carthaginian foragers.

Fabius threatened to starve out Hannibal. His plan, according to Plutarch, was “to send aid to their allies, to keep their subject cities well in hand, and to suffer the culminating vigor of Hannibal to sink and expire of itself, like a flame that flares up from scant and slight material.” He ordered civilians in Hannibal’s path to destroy their crops and buildings and to move to the safety of a fortified town.

Hannibal understood Fabius’s strategy very well. “He therefore made up his mind,” writes Plutarch, “that by every possible device and constraint his foe must be induced to fight . . . . ” At first Hannibal led out his army and approached the Roman camp in battle order. Later he marched from Apulia into Campania, hoping the Romans would fight for this fertile and strategic region. But Fabius refused to take the bait. He allowed Hannibal to raid Campania’s fields and farms.

The Carthaginians gathered a load of plunder, but to their frustration, not a single Italian city south of the Po Valley opened its gates to the self-proclaimed liberators. One more victory was all it would take, Hannibal hoped, to panic the allies into bolting from Rome. But Fabius frustrated him and the allies remained loyal.

Like Memnon, Fabius had strategic insight. Unfortunately for Rome, Fabius resembled Memnon in another way too: he had limited authority, as events showed. Fabius’s way of war made such a mark that, even today, we label a scorched-earth policy “Fabian strategy.” But in 217 B.C., Fabius was not popular. Roman culture worshiped the military offensive and looked down on defense. Fabius’s soldiers bristled at their commander’s passivity, and the Roman public nicknamed him “Hannibal’s manservant.” The final straw came at the end of Hannibal’s raids in Campania.

Loaded with loot, Hannibal hoped to retreat eastward to Apulia, but Fabius blocked off the mountain pass that Hannibal had to take. At the same time, Fabius threatened to attack if Hannibal tried to continue in Campania. It was a trap, but Hannibal wriggled free.

One night Hannibal had his men tie torches to two thousand oxen and drove them over a ridge to lure the Romans after them. The Romans guarding the pass followed on what amounted to a wild-goose chase, thinking they were chasing Hannibal’s army. Meanwhile, Hannibal and most of his army escaped with their loot into Apulia. To the Romans, it was humiliating—and bloody; the Carthaginians killed about one thousand Roman soldiers as a parting shot.

It was a prime example of Hannibal’s agility. A frustrated Roman author, Florus, called it the “art of Punic fraud.” Every time they took a step forward, the Romans found themselves tripping over one of Hannibal’s stratagems.

Fabius’s deputy, the Master of the Horse Marcus Minucius, opposed the dictator’s strategy of attrition. Minucius wanted to fight. The Carthaginian had captured the small city of Gerunium in northern Apulia, slaughtered the population, and used it to house his troops and supplies. When Fabius was temporarily back in Rome, Minucius used the opportunity to attack Hannibal’s men when they were out foraging. Minucius won a minor victory, which he trumpeted as a major success, but Hannibal struck back. He lured Minucius into an ambush. Only the last-minute arrival of Fabius with relief forces saved the day.

Spain: Rome’s Counterattack

By the end of 217 B.C. Hannibal faced frustration in Italy. But even worse news came from Spain. The Romans had sent an army there in spite of Hannibal’s threat to Italy. They defeated Hannibal’s brother Hasdrubal on both land and sea. The Romans conquered Spain’s eastern seaboard and destroyed Carthaginian naval power off the Spanish coast.

What Memnon had wanted but failed to do in Greece, Rome pulled off in Spain. That is, the Romans sent substantial forces to attack the enemy’s base. Rome’s offensive began in fall 218. The ex-consul Gnaeus Scipio (uncle of Scipio Africanus) and his army landed in northeastern Spain. Unlike Hannibal, they had a friendly base, the coastal city of Emporiae (northeast of Barcelona). Hannibal had left Spain under the command of his younger brother. Hasdrubal was renowned for bravery, grit, and dignity, but not for strategic acumen. By the time he marched northward to fight the Romans, Gnaeus Scipio had defeated Carthaginian forces near Tarraco and captured the Carthaginian commander Hanno. Rome now controlled most of northeastern Spain.

The following year, 217, Hasdrubal made a bad situation worse. That summer, he fought a naval battle with Gnaeus Scipio off the mouth of the Ebro—and lost. The Senate was so encouraged that it sent twenty more warships and eight thousand soldiers to Spain under Gnaeus’s brother Publius Scipio—the consul of 218 who fought Hannibal at the Ticinus and Trebbia. Together, the two brothers crossed the Ebro and marched as far as Saguntum, where they freed hostages taken by Hannibal. Various Spanish tribes cast aside their allegiance to Carthage and switched to Rome—or so Roman sources claim.

One thing is certain: the Scipio brothers’ offensive had hemmed in Hasdrubal south of the Ebro. Worse still, from Hannibal’s point of view, Hasdrubal was in no position to send reinforcements. Hannibal’s army was too small to conquer Italy. His plan had always foreseen the need for reinforcements, either from winning new allies in Italy or by getting help from Spain or even Carthage. Except for his Celtic troops from the Po Valley, Hannibal had made no progress in solving his manpower problem.

•  •  •

All in all, Hannibal responded to resistance with mixed results. He was able to brush off the rough crossing of the Apennines with a smashing victory at Trasimene. He humiliated a Roman army and lifted his status among his Celtic allies. When a window of opportunity opened for him to attack the city of Rome, Hannibal knew that his army was too tired and hungry to exploit it. He solved the crisis of his men’s suffering, but only temporarily. Ominously, he had no solution at all to the challenge of the Scipios in Spain. That, in turn, left him without the reinforcements that he desperately needed.

Hasdrubal personified another of Hannibal’s problems: he had no general good enough to entrust with control of another front. Hannibal had no Parmenio, whom Alexander had sent off to Gordium, and no Antigonus, who had skillfully defeated the Persians’ counteroffensive in Anatolia. The Carthaginians lacked bench strength, to use a sports analogy. Hannibal could not be in two places at once, and that problem would bedevil their armies throughout the war.

The lack of a first-rate subordinate in Spain was, so to speak, a weakness in Hannibal’s infrastructure, and it wasn’t the only one. At the end of 217, after more than a year in Italy, Hannibal didn’t have a base. Small and depopulated, Gerunium was no solution. Unless Hannibal got a major city to welcome him, his army would break apart soon enough. But no city would accept Hannibal unless he won another victory.

Hannibal had not broken Rome and he remained far from his goal of bringing Rome to the negotiating table.

We might argue that with the Scipios advancing in Spain and Fabius blunting the edge of Hannibal’s offensive in Italy, Rome was winning. Yet Carthage would strike back in Spain and Fabius left office in Rome by the end of 217. Luckily for Hannibal, Minucius represented Rome better than did Fabius.


Unlike Darius, Pompey had no intention of giving his enemy pitched battle. Pompey had no illusions about his chances against Caesar’s veteran legions. Instead, he would make Caesar dance to his tune. At least, he would try.

The Dunkirk of Italy

For Pompey, Brundisium was where the real war began. Brundisium was his Dunkirk. Dunkirk, of course, symbolizes British resistance to Nazi Germany. When the Germans invaded France in May 1940, they cut off Britain’s huge army and threatened to destroy it. But the British retreated to a French city on the English Channel: Dunkirk. From there the British evacuated most of their army by ship to England. It was a brilliant operation, the first step on the road back to victory.

Brundisium (modern Brindisi) was an Italian city on the Adriatic Sea to which Pompey’s men retreated from Caesar. Located at the southern end of the Appian Way, Brundisium was the main port for sailing to Greece. From there, in March 49 (by the Roman calendar, January 49 by the solar calendar), Pompey evacuated about 27,000 men in two sailings. It was the nucleus of the new army that he was building in Greece.

Pompey was a first-class strategist. He implemented a variant of Fabius’s strategy: refusing to fight. Each man withdrew his army from the battlefield, if in a different manner. Fabius didn’t have a strategy for victory, however, merely for avoiding defeat. Pompey had a strategy for victory, but some questioned whether he would be fast or aggressive enough to employ it against Caesar—or whether his rivals in the Senate would trip him up, as they had at Corfinium. Brundisium would be a big test.

Caesar arrived at Brundisium on March 9 with six legions, three veteran and three new. Pompey’s fleet had already left, ferrying off about half of his army as well as the two consuls and a large number of senators, though not Pompey himself. The ships would land at the major port city of Dyrrachium (modern Durrës, Albania), disembark the men, and pivot back to Brundisium to pick up the other half of the army. Pompey was still there, waiting to direct their final escape.

Caesar sent two high-ranking officers to negotiate with Pompey: Pompey’s chief engineer, captured by Caesar, and one of Caesar’s commanders who was friends with a leading Pompeian officer. Caesar asked Pompey for a face-to-face meeting; surely they could iron out their differences. Pompey sent his regrets that, with the consuls already gone, his hands were tied. It made a good show. Neither man wanted the blame for war but neither intended to give an inch.

The real action was taking place in and around the port. Like Alexander, Caesar wanted to defeat his enemy’s navy on land. Brundisium’s harbor was shaped something like an inverted letter Y. The fortified city was located between the two oblique arms of the letter. The harbor emptied out into the Adriatic through the letter’s perpendicular leg. Outside the city walls, and at the spot where the arms met the leg, the mouth of the port was at its narrowest.

It was here that Caesar had his engineers try to block off the harbor. They built a barrier, starting at each shore with breakwaters and earth banks that were joined, in the deep water, by a series of anchored rafts to close the gap. Then they erected screens and towers to defend the barrier against attack by ships or fire.

Caesar was audacious, but so was Pompey. He seized large merchant ships, outfitted them with three-story towers, armed them with catapults, slingers, and archers, and launched them against Caesar’s rafts. The two sides thrusted and parried for over a week, which kept Caesar from completing his barrier.

By then, Pompey’s ships had returned from Dyrrachium and picked up the rest of his forces. He left behind only a few light-armed veterans to mount the walls. When the signal came to go, they would have to retreat quickly to the harbor, with Caesar’s men coming over the walls after them. But Pompey’s troops knew the way, while the enemy would have to contend with walls and stake-filled trenches left to slow them down.

Pompey timed his ships’ departure to take place at nightfall. The gathering darkness put Caesar’s men at greater risk of falling into the Pompeians’ traps. The townspeople helped Caesar’s soldiers make their way to the harbor, either because they were pro-Caesar or just pro-survival. Still, they had to wind their way around the barriers and by the time they reached the harbor, all of Pompey’s ships had escaped except for two that had caught on Caesar’s breakwaters. It was March 17, 49 B.C.

For Pompey, Brundisium was a great success. Some people, wrote Plutarch, consider the evacuation “among his best stratagems.” Caesar feigned surprise that Pompey had given up Italy without more of a fight, but he knew better. Yet “wars are not won by evacuations,” as Churchill said after Dunkirk.

Caesar held Italy, which he had conquered in less than two months. The masses showed no sign of opposition; on the contrary, they prized both the cash he had sent from Gaul and the mildness of his men since crossing the Rubicon. The few senators left in Italy were less impressed. Caesar won little new support when he finally entered Rome soon after leaving Brundisium. What he did get was money—a king’s ransom, in fact, from the treasury. But to get it, Caesar had been forced to threaten to kill Lucius Metellus, a tribune of the people who had blocked his way. For once he dropped the mask of clemency.

Thunder in the West

The conquest of Italy did not put Caesar in control. On the contrary, it made him a target. Pompey flanked him on either side. In the west, Pompey’s stronghold was Spain. He had close to 100,000 men there. His main force consisted of 5 legions, 80 cohorts of Spanish auxiliaries, and 5,000 cavalry: a total of 70,000 men. Another army, consisting of two legions as well as auxiliaries, was stationed in western Spain.

In the east, Pompey had five legions or about 27,000 men, with the potential of more to come from new recruits. He could train them while gathering support from the eastern provinces that he had conquered and organized for Rome in the 60s B.C. Meanwhile, Pompey controlled the sea. He could use his ships to prevent the shipment of grain to Italy. Since Italy could not grow enough food for its own needs, the result would be to starve out Caesar.

Caesar, then, couldn’t afford to rest in Italy. He had to go on the attack and he had to do so immediately—but not recklessly. He might have been itching to go after Pompey, who was just a short trip away across the Adriatic, but Caesar was as shrewd as he was aggressive. Caesar could not afford to leave those Spanish armies in his rear when he turned eastward because they might join Pompey. But unless Pompey sailed to Spain to join them, they lacked good leadership. So he attacked Spain first. In spite of his famous boldness in battle, Caesar’s strategy was methodical, even cautious. He would take out the enemy’s strengths piecemeal, one by one.

Caesar had another, less complicated reason to begin with Spain: he could get there. He had enough ships to send three legions, commanded by Curio, on an expedition to Sicily, Sardinia, and North Africa (modern Tunisia), all key sources of Italy’s food supply. But that was it for his fleet; Caesar could reach other places only by land. Excellent roads linked Italy and Spain via Gaul. Poor roads and hostile tribes lined the land route to Greece. For Caesar, therefore, all signs pointed to Spain.

Although he was an invader, like Alexander, in attacking Spain, Caesar behaved more like Memnon. Just as Memnon went after Alexander’s “soft underbelly” in Greece, so Caesar went after Pompey’s “soft underbelly” in Spain.

As he left for Spain, Caesar is supposed to have told his friends that he was going against an army without a leader and that he would return and fight a leader without an army. He meant that the enemy had many troops in Spain but not Pompey, while Pompey had far fewer troops with him in the east.

On the way to Spain, Caesar ran into an obstacle at Massilia (Marseille), an important city that closed its gates to him. Caesar’s old enemy Lucius Domitius Ahenobarbus, last seen at Corfinium, was there; Pompey had sent him to take charge of the defense of Massilia. Caesar moved on and left a force behind to besiege the city, but he dearly felt the absence of Masillia’s rich supplies. Yet in spite of these setbacks, Caesar conducted another lightning campaign. How did he do it—and do it against Pompey’s hardened and veteran Spanish troops?

It helped, of course, that Pompey was passive. Pompey was the opposite of Caesar, because Pompey joined a bold strategy with operational timidity. On the strategic level, Pompey risked everything on giving up Italy and building a new army in the east. But when it came to actual military operations, Pompey handed over the initiative to Caesar. Alexander had made a similar mistake with Memnon and the Persian navy, but Divine Providence stepped in and saved Alexander. Pompey was not as fortunate. He learned a harsh lesson in the cost of letting the enemy decide when and where to fight.

Spain is a good example. Instead of waiting for Caesar to invade Spain, Pompey could have seized the reins by marching his men from Spain to attack Caesar in Italy. Better yet, he could have gone to Spain himself to take command. Instead, he left everything to his generals in Spain, Lucius Afranius and Marcus Petreius. They were good and experienced commanders, but Caesar was already a living legend. Only Pompey himself could keep his men’s morale up if the going got rough—as it surely would against Caesar.

The conqueror of Gaul was dangerous beyond measure once he got near the combat zone. Spain was no exception. As soon as he arrived, Caesar displayed the qualities for which he is famous: audacity, agility, good judgment, a strategy that mixed military force with political persuasion, and the leadership skill to hold his men together despite defeat. He turned his weaknesses into strengths and pressed his advantages to the hilt.

Caesar found the Pompeians west of modern Barcelona, near the town of Ilerda (Lérida) on the Sicoris (modern Segre) River. He went rapidly on the attack. Caesar’s forces had more cavalry but the two armies were evenly matched in infantry, and the Pompeians held their own, so the attack failed. Caesar planned to go back on the offensive, but first he needed access to food and supplies. The situation was difficult, though, because Pompey’s men held the best ground, and the collapse of a bridge over the river further cut off Caesar.

As usual, failure only made Caesar try harder. What he did was both resourceful and energetic. He had his men build small boats, carried them on wagons about twenty miles to a good crossing point, ferried a legion across, and had them build a new bridge. It proved to be a war-winning operation. Caesar could now harass the enemy with his superior cavalry. In addition, he brought his diplomatic skills to bear and began to win over local tribes that had long hated Pompey. They furnished supplies for Caesar’s army.

Afranius and Petreius saw the tide turning so they chose to move to safer territory. It would not be easy to outrun Caesar, especially not when he had more horses. He not only followed the enemy but headed them off, which he was able to do by another bold operation: he had thousands of his soldiers wade through the freezing water of the Sicoris. Caesar and his men, now well supplied themselves, trapped the Pompeians without supplies. They merely had to wait for the enemy to give up. To hasten that, Caesar encouraged his men to mix and mingle with the soldiers in the enemy army. This was not difficult to do, as the two forces were camped near each other, and they both, after all, were Roman. The plan worked and the Pompeians surrendered. Caesar pardoned them and some of them joined his ranks. Meanwhile, Pompey’s other forces, in western Spain, quickly surrendered as well.

It took Caesar only three months to conquer Spain and disarm Pompey’s best troops, and he did it with little or no bloodshed. It was a triumph of maneuver warfare. Caesar could now turn eastward to Pompey without worrying about an attack from Spain on Gaul or Italy. Meanwhile, Masillia finally fell to him, after a months-long siege, in spite of reinforcements sent by Pompey. Domitius escaped.

Not everything had gone well for Caesar, though. After taking Sardinia and Sicily, Curio had met with disaster in North Africa. The Numidian king Juba, a Pompeian ally who loathed Caesar, sprang a trap for Curio. The Romans lost virtually all ten thousand to fifteen thousand men in their three legions and Curio himself was killed. The loss cut off the people of Italy from a major source of grain. Another setback came in the Adriatic Sea, where Pompey’s navy put one small Caesarian fleet out of action and captured another, adding an additional five thousand to seven thousand men to their forces.

In fact, no fewer than three of Caesar’s generals had gone down in death or defeat in recent months. Never mind: Caesar himself still strode, magnificent and conquering. Pompey still remained on the defensive. He might have sent a fleet across the Adriatic to bottle Caesar’s forces up in Brundisium. He did not, though, and that left Caesar free to move east when he was ready.

Still, there was the enemy within. Caesar’s own troops mutinied in Placentia (modern Piacenza) in northern Italy. Civil war frustrated them. The war in Gaul had left them awash in loot, but this time, they had to show clemency and restraint when they wanted more loot. Caesar took a hard line in response. Instead of negotiating, he called an assembly of the entire army. When he rose to speak, Caesar defended the principles of discipline and patriotism. He insisted that Italy must not be sacked. Then, he followed the old Roman strategy of divide and conquer, by singling out one legion. The ninth legion had led the mutiny, and now Caesar promised to decimate it. Decimation was an old-fashioned punishment in which every tenth man was executed. The rest of the army begged for mercy, and Caesar agreed to be satisfied with the heads of a dozen ringleaders. Caesar had won, as one source says, “not through lenience but by the authority of the leader.”

The mutiny was over and the army was bound even closer to its commander than before. Rebellion and repression: a ritual dance, no doubt, but Caesar’s mastery of the steps might have made his enemy shiver.

Bring Me the Head of Julius Caesar

After grabbing Spain and its armies from Pompey, Caesar deserved a break, especially in the wake of mutiny and defeats elsewhere. But, being Caesar, he plunged into another offensive instead. After returning to Italy at the end of 49 B.C., he spent only eleven days in Rome. It was time enough to have himself elected consul and to impress the public with his moderation. Standard behavior in Rome’s civil wars was to round up one’s enemies for execution; Caesar continued his policy of clemency instead. Once again, Caesar distinguished his brand.

Caesar now began a very risky military operation, which he had a real chance of losing. Strategically, however, it was a sober choice. It would have been suicide to stay in Italy and wait for Pompey to invade in the spring—with a grand fleet, an ever-growing army, and a limitless supply of money. While Caesar had conquered Spain and lost North Africa, Pompey had gathered a massive army, which he had begun training vigorously. He had 9 legions, with 2 more on the way, as well as 5,000 light infantry and 7,000cavalry, a total of roughly 55,000 men. Caesar had 12 legions and 1,000 cavalry, but attrition had cut his legions down to 2,000 to 3,000 men instead of the full complement of 4,800, for a total of roughly 30,000 men.

Pompey’s army greatly outnumbered Caesar’s, and Pompey threatened to come roaring after him as soon as Pompey was ready. Toward the end of the year 49 B.C., Pompey finally gained the title of supreme commander. It wasn’t quite enough to corral the senators and aristocrats who sat in his councils of war, each of them convinced that he knew more than the man who called himself “the Great,” but at least Pompey now had legal authority.

Many men admired the supreme commander but few gave Pompey the kind of loyalty that Caesar’s troops had rendered him ever since Gaul. They were, as a Roman writer put it, “et devotissimi . . . et fortissimi”: both extremely devoted and extremely brave. Caesar had that advantage, and he grabbed another advantage in turn—surprise. As he is said to have told his army around this time, “the most potent thing in war is the unexpected.” In short, things had changed little since the Rubicon: if he wanted to stay in power, Caesar had to attack.

He began with a gamble. He shipped his men across the Adriatic Sea from Brundisium in late autumn—January 4, 48 B.C. (early November 49 B.C. by the modern calendar). It was about one year since he had crossed the Rubicon. Because he had no warships, Caesar used merchant ships. Because he lacked enough ships to transport all his men, he took only half of them. Expecting that Pompey’s fleet would have its guard down, he hoped to slip by them and land on the Albanian coastline, and he succeeded. Once on the alert, however, the Pompeians prevented Caesar’s ships from returning to Italy. It took four months before Caesar’s lieutenant, Mark Antony, finally had the chance to evade Pompey’s fleet and bring the rest of Caesar’s troops across the Adriatic.

Alexander too had moved rapidly and decisively in his day, but Caesar took greater chances. Like Caesar, Alexander set out against his main enemy about one year after first launching his invasion (Alexander crossed the Dardanelles in spring 334 and marched toward Darius in spring 333). But Macedonian troops had invaded Anatolia two years earlier and begun laying the groundwork for victory, giving Alexander a head start compared with Caesar. Nor did Alexander do anything as drastic as ship an army across the sea in late autumn. The truth is, Caesar darted ahead of Alexander.

When he crossed the Adriatic, Caesar landed on the coast of Epirus (roughly, modern Albania). His ultimate target was Dyrrachium, about seventy-five miles to the north as the crow flies. Dyrrachium was a Roman naval base at the head of the via Egnatia, the road that led eastward through Epirus, Macedonia, and Thrace (modern Albania, Greece, and Turkey) to Byzantium (Istanbul), linking the Adriatic and the Bosphorus. Pompey planned to winter in Dyrrachium with his army and to cross to Italy as soon as the spring sailing season began. Then he planned to crush Caesar.

But with so few forces at his disposal, Caesar was in no position to attack Dyrrachium. The most he could do was make threatening moves in its direction by taking a few towns that lay on the way. As it happens, Pompey and his army were to the east of Dyrrachium at the time, but they hurried there at the news of Caesar’s arrival and beat him to the city.

Then one of those little things happened, one of those rare moments of enlightenment in the fog of wartime. It took place during one of the stabs at negotiation that Caesar made from time to time. He was, after all, a great politician as well as a great general, and he knew how much the average Roman yearned for peace. So, as he had done earlier outside Brundisium, Caesar now called for talks.

Pompey said no. He was ahead in the military game and he had no intention of throwing away his advantage. Still, refusing the offer made him seem unreasonable. Even some of his men thought so: since the two armies were camped close to each other, Caesar sent a negotiator to Pompey’s troops, and they welcomed him. But Pompey’s officers firmly opposed talks and one of them came forward and started arguing with Caesar’s representative. Suddenly, Pompey’s soldiers began to throw javelins and wounded a number of Caesar’s men.

The peace talks collapsed but not before one of Pompey’s lieutenants laid things on the line: “There can be no peace for us,” he said, “until Caesar’s head is brought in.” The Latin rings with power: nam nobis nisi Caesaris capite relato pax esse nulla potest.

It boiled the war down to its essentials—one man. As long as Caesar was alive, peace was impossible. He would never back down. If he died, no one else could hold his army together. But Pompey’s death would have been a different story, engendering among his supporters an equal measure of mourning and relief. His goal was power but theirs was a republican government, and they would be glad to go on fighting for it without him. Without Caesar, though, there would be no Caesarians, as the followers of Caesar were called.

If Pompey thought he could win a direct assault on Caesar, he would have made one. He preferred instead to starve out the enemy. It was Pompey’s by-now-familiar caution, but it made sense, as the enemy had limited food and supplies and no way to return to Italy.

The situation drove Caesar to distraction. At one point, he made the improbable move of slipping out of camp and hiring the captain of a small boat to bring him back to Brundisium. The weather turned rough and the captain wanted to turn back, but Caesar insisted on continuing because of “Caesar’s good fortune.” Luckily, Caesar came to his senses before the boat was swamped and returned to shore. Was it just a stunt to boost morale? Back at his camp, Caesar’s men hailed his safety and vowed to beat Pompey without reinforcements, all on their own.

They didn’t have to. Three months after their arrival, in April 48 B.C. (February 48, by the modern calendar), Antony finally managed to show up with the rest of Caesar’s legions. Once again, Pompey’s blockade had failed. In fact, the fault looks even greater when we consider that a Pompeian squadron of fifty ships raided Antony’s base at Brundisium. Antony fought them off, but just think what a full-scale attack could have achieved. As so often, Pompey gave up the initiative to the enemy.

Antony had actually been driven off course and landed forty miles north of Caesar. Caesar marched north to meet him, and Pompey tried to block him. Pompey failed in that, although his navy did manage to capture all of Antony’s ships, leaving Caesar’s forces cut off from Italy. Ever wily, though, Caesar beat Pompey back to Dyrrachium and cut him off from his supplies in the city. Pompey made camp on Petra, a fortified hill near the sea and a harbor, with Dyrrachium to his north and Caesar’s camp in between.

And there, the two sides sat and dug in. After more than a year of mobile warfare from Spain to the Adriatic, the struggle to control the Roman empire settled down to a rumble over a twenty-mile-square strip of hills and sand on the coast of Albania.

Pompey’s Game

Caesar had cut Pompey off from Dyrrachium but only by land. Since Pompey held command of the sea, he could ferry supplies to Petra. Caesar couldn’t stop that, but he could prevent Pompey from sending his cavalry into the hills in search of the fodder they needed for their horses.

It was a small victory but Caesar wanted to turn it into a big one. He decided to have his men build a wall, punctuated by forts, to blockade Pompey’s army. The wall eventually stretched for seventeen miles over hilly terrain. Pompey answered by building a fifteen-mile long “counterwall” to keep Caesar’s army away from his troops. There now followed the strangest battle of the war. For more than three months, the two sides were locked in a kind of armed wrestling match of raids and counter-raids.

It was a war of attrition, and attrition was Pompey’s element. He was a great organizer who liked nothing better than to twist the noose slowly around another army’s neck. Caesar was all speed. He jabbed brilliantly, looking for an opening against the foe, but Pompey ground him down.

Caesar made the mistake of playing Pompey’s game at Dyrrachium, although he tried to play it differently. As soon as he linked up with Antony, Caesar challenged Pompey to a pitched battle against his reunited forces. But Pompey was too smart to fall for that, knowing that his men were not ready to take on Caesar’s veterans in deadly combat. Later, on another occasion, Caesar led an assault on the city of Dyrrachium, but it nearly cost him his life, and the attempt failed. So Caesar put his hopes in his wall.

As a military strategy, it could hardly succeed. The wall would reduce Pompey’s supplies but not destroy them. Cut off from the city and the sea, Caesar’s men would suffer more. It was nearly a year since the last harvest, and there was little food to be found by foraging. In fact, Caesar’s troops were reduced to eating roots, which left Pompey to dub them animals and not men.

But the wall’s purpose was as much political as military. It meant to humiliate Pompey by showing that a smaller army could cut him off—an army that he feared to face in conventional battle. Dolabella, who was with Caesar at Dyrrachium as an officer—apparently forgiven for earlier losing a fleet in the Adriatic—wrote to Cicero, his famous father-in-law, to tell him to dump Pompey and switch to Caesar’s side, because only losers allow themselves to be blockaded.

“So what?” Pompey might have responded, and rightly so. (Cicero stayed loyal to Pompey, by the way). Pompey figured that eventually Caesar’s men would crack, and they did. After three months of siege, two of Caesar’s Gallic cavalry officers defected to Pompey because Caesar had caught them stealing money. They brought key intelligence about weak points in Caesar’s defenses. In early July (early May by our calendar), Pompey launched a series of joint land-sea attacks. Although Caesar’s forces managed to drive them back, it was not easy, and they took heavy casualties. Caesar himself had to jump in at the head of the reserves.

Not long afterward, Caesar led a counterattack. At first it went well, but then, to quote Caesar, “fortune . . . produces great changes out of little movements, as it happened then.” Caesar’s men mistakenly entered a kind of maze of abandoned walls and ditches. They paid for their error—Pompey attacked them and they panicked. Caesar now risked his life—and almost lost it—in an effort to stop them: the incident with which this book began.

But not even Caesar could stem the tide of panic. The result was a major disaster: about a thousand of his men, including thirty-two officers, were killed and others taken prisoner. Also lost were thirty-two battle standards, a sign of shame to a Roman army.

Caesar’s position looked grim, but then a surprising thing happened: nothing. Caesar expected Pompey to close in for the kill but Pompey held back. He suspected an ambush and he thought it was an unnecessary risk to attack. As far as he was concerned, he had won the war. He expected that Caesar’s hungry and defeated army would simply break up. If they managed to hang on, they could no longer do real damage.

Pompey’s soldiers now saluted him as “Imperator!”—that is, “victorious general.” Jubilant, Pompey accepted the tribute, but he didn’t repeat it. Calling himself “Imperator” would offend many, because in this case, the title came from a battle in which he had killed fellow Romans, not foreign enemies.

Anyway, Pompey had a bigger problem to worry about. Caesar was unbeaten. Caesar had expected Pompey to follow up his success and deliver the crowning blow, but he never came. Caesar felt surprise and contempt. He said to his friends, “Today the enemy would have won, if they had a commander who was a winner.”

Looking back later, Caesar accused Pompey of overconfidence, and of forgetting that the victory was due more to Caesar’s men’s bad luck than to any prowess on Pompey’s part. By not finishing the job, Pompey gave Caesar breathing space to come up with a new plan, while not bothering to do the same himself, as Caesar later sneered.

Caesar had no intention of giving up. Success spoiled Pompey, but failure stiffened Caesar’s spine. He realized that he was finished at Dyrrachium. Better withdraw eastward, over the mountains into central Greece, specifically into the rich and fertile region of Thessaly. By now, it was mid-July (mid-May by our calendar) and the winter wheat would be ripening in the fields. Caesar’s men could harvest it and eat. He also recognized that he needed to rebuild his men’s morale before risking another fight. He gathered the army, told the troops to take heart, and punished a few of his standard-bearers for good measure. Then, after sending the baggage train ahead at night, he withdrew his army at dawn.

In private, Caesar is supposed to have confessed that he was wrong to blockade Dyrrachium. In public, he admitted nothing. He told the troops that they should blame their loss on anyone but him. It was arrogant but shrewd. Caesar considered the army to be like a child that would be lost without faith in its father—himself. Shake that trust and he would orphan them.

As he retreated to Thessaly, Caesar did nothing less than save his army. It was an inspired display of leadership. No surprise, for, aside from the strategic blunder of blockading Dyrrachium, Caesar had offered brilliant leadership throughout the winter—spring campaign of 48 B.C. He led at every level, from the front line to intermediate-sized units to the strategist’s tent. He led directly and indirectly, by example and by mental agility. He showed an extraordinary knowledge of his men and clearheadedness about their strengths and weaknesses. He accepted setbacks but never defeat. Caesar proved himself to be a man without illusions but also without gloom.

When it came to cunning and strategic insight, Pompey was Caesar’s equal. In organizational skill, Pompey was his superior. His strategic withdrawal from Italy was masterful. His defense of Dyrrachium was shrewd. But he lacked Caesar’s audacity and speed. His army could not compete in pitched battle. He failed to destroy Caesar when he had him at his mercy at Dyrrachium. Worst of all, Pompey was capable of self-delusion. Eventually, Caesar too would fall prey to this weakness, but in 48 B.C., his mind was still as cold as the snows of Gaul and as sharp as a wolf’s tooth.

The Essence of Decision

“War is a harsh teacher.” After his experience in the first year and a half of war, each of our three generals would have nodded in agreement to this saying of Thucydides. They each faced surprises and reversals.

About a year and a half after the outbreak of war, Hannibal and Caesar had each penetrated to the heart of enemy territory. Although they took great risks to get there, neither succeeded in conquering his opponent’s stronghold. Caesar was driven back from Dyrrachium, while Hannibal didn’t even try to take Rome. Neither man had taken his last shot yet, however—far from it.

About eighteen months after the start of his war, Alexander had not yet reached the enemy’s homeland, but he had conquered its rich, western rim. Like Hannibal, he had defeated the enemy in two pitched battles; Hannibal also won a third battle that was effectively a massacre. Caesar hadn’t found an enemy willing to fight him in a pitched battle, but he had conquered Italy and Spain as well as Sicily and Sardinia even so, with seemingly little effort.

Alexander, Hannibal, and Caesar each found himself challenged by the enemy’s game. Each man began the war with the hope that the enemy would honor the standard protocols of warfare in the Greek, Carthaginian, and Roman worlds: decision by pitched battle. The enemy had other options, though, and he chose to exercise them, and none of the three would-be conquerors found it easy going.

Take Alexander. When he crossed the Hellespont, he thought that he had a viable fleet. He quickly came to the conclusion that he didn’t, and sent most of his ships home. But he was hasty, as the fleet would have come in handy in later operations. Alexander thought that he could shut down the Persian navy by making war on it by land and taking its naval bases. He turned out to be too optimistic. The siege of Halicarnassus was costly and left the harbor in Persia’s hands. Some of Persia’s ports on the mainland proved too difficult to take, and Persia easily reconquered the islands that had gone over to Alexander. In Memnon of Rhodes, Alexander had a frighteningly competent opponent. In fact, a year after he invaded Anatolia, Alexander faced the real threat of a Persian invasion of Greece.

Two things saved him. First and foremost, Divine Providence intervened. Memnon died of a sudden illness in spring 333. Second, Alexander had superb strategic intuition, which let him guess Persia’s default mode correctly. As soon as Memnon died, Darius called off the invasion of Greece and called his Greek mercenaries into service in a land battle against Alexander instead. For Persia, it was strategic suicide. For the Macedonians, it was confirmation of the enemy’s fatal flaws.

Hannibal too learned hard lessons. Losing the sight in one eye was the least of them for a tough soldier. He faced the frustration of leading an army that was too tired to make more of its victory than to eat and rest. He got the first glimpse of an enemy that, no matter the size of its defeat, had no intention of surrendering. And he learned that Rome knew how to fight back, not merely with power but cunning.

By its attack on Spain, Rome threatened Hannibal’s base. It demonstrated as well a strategic tenacity that Persia lacked. In order to respond, Hannibal needed support and reinforcements. The home government in Carthage could provide those in time, if it agreed. What it could not provide, however, was another general as good as Hannibal. The great man had no peer.

Fabius’s strategy in Italy might have troubled Hannibal even more than the battle for Spain. If the Romans avoided pitched battle, he could not win but at best survive. Hannibal needed big victories to attract allies away from Rome and toward him. Otherwise, his small army could harass the Romans but not defeat them. His main hope was to lure Rome back into the arena of pitched battle. It was a good hope, as things turned out, because the Romans did not stick to Fabius’s strategy.

As for Caesar; he had the most serious trouble of all with an enemy who refused to play by his rules. That reflected both Pompey’s clearheadedness and Caesar’s philosophy of the offensive. Had Caesar been less aggressive, he would have evacuated Dyrrachium when Pompey’s refusal to fight a pitched battle there became clear. Instead, Caesar could have gone to Thessaly and either tempted Pompey into battle there or at least wintered in easier conditions. But Caesar risked everything on a battle of attrition at Dyrrachium,where he stood at a distinct disadvantage. Like Fabius, Pompey preferred attrition to pitched battle. At Dyrrachium, Caesar lost not only the battle but nearly the entire war. Only Pompey’s overconfidence allowed Caesar to live to fight another day.

Like Hannibal, Caesar suffered from a subordinate who was not up to his level of competence: Curio lost North Africa for Caesar as Hasdrubal had cost Carthage major setbacks in Spain. Alexander did better with Antigonus in Anatolia.

After eighteen months of war, all three men had suffered setbacks. Alexander had responded most effectively, but he faced the least competent enemy. Caesar was in the most serious trouble, Hannibal somewhere in between.

But the period of coping with the enemy’s initial resistance was over. Each of our generals was about to face a crisis that could decide the war.

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