Military history



I am a success today because I had a friend who believed in me, and I didn’t have the heart to let him down.

—quote attributed to ABRAHAM LINCOLN

THE SHARP-DRESSED STRANGER wore a heavy gold ring on his left hand. He was tall, perhaps six feet or so, sixty-five years of age, and “very erect and commanding in his appearance.” As he rode his horse through the center of the village on a fine, clear day in July 1847, it was obvious that trouble was coming.

Henry Hunt, the owner of a general store at the center of town, knew all too well what would happen next. Few outsiders ever troubled to visit Dundee, a quiet Illinois farming settlement about fifty miles northwest of Chicago. Lately, the appearance of a visitor signaled that a ruinous flood of counterfeit coins and notes was about to wash over the town. Hunt’s business had barely recovered from the last wave of bogus currency, and he was determined not to let it happen again. In his view, there was only one man who had the skills to deal with the matter. Keeping an anxious eye fixed upon the stranger, Hunt sent his errand boy to fetch Allan Pinkerton, the town cooper.

“I was busy at my work,” Pinkerton recalled, “bareheaded, barefooted, and having no other clothing on my body than a pair of blue denim overalls and a coarse hickory shirt—my then almost invariable costume—but I started down the street at once.”

Arriving at the store, Pinkerton found Hunt and another shopkeeper, Increase Bosworth, waiting behind the counter. “Come in here, Allan,” Hunt said, leading him to a room at the back of the store; “we want you to do a little job in the detective line.” Pinkerton greeted this proposal with a burst of incredulous laughter. “Detective line!” he cried. “What do I know about that sort of thing?”

It was a fair question. Pinkerton was still a newcomer in Dundee, struggling to make a success in the coopering trade. After his turbulent departure from Scotland five years earlier, he and his bride had alighted briefly in Chicago, where his old friend Robert Fergus helped him land a job at the Lill & Diversey brewery, making beer kegs for fifty cents a day.

Soon, Pinkerton set his sights on a business of his own. In the spring of 1843, he heard talk of a community of Scottish farmers on the Fox River in Kane County, and he realized that there would be plenty of work for a man who could make barrels, churns, and tubs. He told Joan that he would go ahead and “get a roof over my head” while she waited in Chicago.

For Joan, married barely one year, it was a tearful parting. After a lingering farewell on the banks of the Chicago River, Pinkerton turned and crossed a pontoon bridge, his bag of tools slung across his shoulder. Upon reaching the other side, he looked back and waved, then set off into the tall grasses that lay beyond, whistling a Scottish ballad. “I couldna bear it when the great grass swallowed him up so quick,” Joan recalled, but long after he disappeared from view, she could hear him whistling, and was comforted by the thought that “there’d be a wee home soon for us.”

In Dundee, near a bridge that crossed the Fox River, Pinkerton hand-built a small log cabin and work shed. Farmers and cattle drovers passing on their way to market could not fail to notice the bright new sign: ALLAN PINKERTON, ONLY AND ORIGINAL COOPER OF DUNDEE. After a few weeks, he headed back to Chicago to collect Joan, who soon turned her hand to growing vegetables and tending chickens. “In the little shop at Dundee,” she recalled, “with the blue river purling down the valley, the auld Scotch farmers trundling past with the grist for the mill or their loads for the market, and Allan, with his rat-tat-tat on the barrels, whistling and keeping tune with my singing, were the bonniest days the good Father gave me in all my life.”

Pinkerton, too, seems to have enjoyed the quiet charms of Dundee, and his hard work soon brought dividends. By 1846, he had eight men working for him, a mix of fellow Scots and more recent German immigrants. “I felt proud of my success,” he wrote, “because I owed no man.” Pinkerton’s family, too, was growing. In April of that year, Joan gave birth to a son—the first of six children—named William, after both of his grandfathers.

Now twenty-seven, Pinkerton became regular, even rigid, in his habits, going to bed each night at 8:30 and rising each morning at 4:30, a schedule that seldom varied for the rest of his life. He neither drank nor smoked, but he might indulge himself at bedtime with a novel by Edward Bulwer-Lytton, whose florid historical melodramas, widely ridiculed today, were hugely popular at the time. Though Pinkerton would surely have read the novel Paul Clifford—with its much-parodied “dark and stormy night”—his favorite was Eugene Aram, which drew on the career of a real-life murderer and his eventual capture. At the outset, Bulwer-Lytton declared his belief that the case was “perhaps the most remarkable in the register of English crime,” and he insisted that the reader must examine the “physical circumstances and condition of the criminal” in order to “comprehend fully the lessons which belong to so terrible a picture of frenzy and guilt.” These lessons were not lost on Pinkerton, who judged the novel to be the greatest ever written. As a Dundee friend later recalled, “He didn’t think much of you if you disagreed with him on that.”

If Bulwer-Lytton fired his imagination, Frederick Douglass sparked Pinkerton’s conscience. The newspapers at that time were filled with stories about Douglass, the escaped slave whose 1845 memoir—Narrative of the Life of Frederick Douglass, An American Slave—was becoming a touchstone of the abolitionist movement. Pinkerton was deeply moved by Douglass’s struggle, as well as by his eloquence. Soon, the political ideals of Pinkerton’s Chartist days found a new channel. “This institution of human bondage always received my earnest opposition,” he later wrote. “Believing it to be a curse to the American nation, and an evidence of barbarism, no efforts of mine were ever spared in behalf of the slave.” The first of these efforts, it appears, was to offer his services to Charles V. Dyer, a leading force in the Chicago chapter of an organization called the American Anti-Slavery Society. Dyer soon found a way for the only and original cooper of Dundee to make himself useful.

The Underground Railroad—a secret network of meeting points, back-channel routes, and safe houses used by abolitionists to ferry runaway slaves north to free states and Canada—had been up and running for many years by this time. Writing in 1860, one former slave claimed that the operation got its name from a disgruntled slaveholder who could not understand how his “escaped chattel” had disappeared so completely: “The damned abolitionists must have a railroad under the ground,” he complained. Pinkerton admired the cunning and subterfuge of the enterprise. The circuitous routes were changed frequently to throw marshals and bounty hunters off the track, and the organizers made use of coded railroad terminology to protect the individual components of the system from discovery. The planners of the escape routes were known as “presidents of the road,” the guides who escorted the fugitives from place to place were “conductors,” the hiding places and safe houses were “stations,” and the ever-changing routes were “lines.” The fugitives themselves were variously known as “passengers,” “cargo,” or “commissions.”

Within months, Pinkerton’s log cabin on the Fox River would become an active station on the Underground Railroad, being a useful stopping point on the journey north to Wisconsin and Canada. Though some of the Illinois stationmasters would be prosecuted for harboring slaves, Pinkerton made little effort to conceal his activities. Some of his passengers stayed long enough to receive instruction in the basics of barrel making, in the hope that the skills might prove useful to them as free men. Years later, Pinkerton spoke feelingly of his efforts at this time, and of his growing awareness that the issue of slavery threatened to divide the nation. “Above all,” he said, “I had hoped for the oppressed and shackled race of the South that the downfall of slavery would be early accomplished, and their freedom permanently established. I had the anti-slavery cause very much at heart, and would never have been satisfied until that gigantic curse was effectually removed.”

For the moment, at least, Pinkerton had more immediate concerns. Although he claimed to be content with his “quiet, but altogether happy mode of life” in Dundee, he often found himself pressed for cash. “There was plenty of dickering, but no money,” Pinkerton complained. “My barrels would be sold to the farmers or merchants for produce, and this I would be compelled to send in to Chicago, to secure as best I could a few dollars, perhaps.” A series of bank failures earlier in the decade compounded the problem. “There was but little money in the West,” he wrote, and a workingman such as himself “could get but little.” Looking to save whatever he could, Pinkerton found ways to scavenge for the raw materials he needed for his barrels and casks. “I was actually too poor to purchase outright a wheelbarrow-load of hoop-poles, or staves, and was consequently compelled to cut my own,” he recalled. To this end, he often roamed along the banks of the Fox River, and in time he found a small island a few miles north “where the poles were both plentiful and of the best quality.”

One day, as Pinkerton took a raft upriver to cut a fresh supply, he stumbled across the smoldering remains of a campfire. For months, he had heard talk of gangs of counterfeiters in the region and concluded that the island was being used for unlawful purposes. “There was no picnicking in those days,” he recalled, “people had more serious matters to attend to, and it required no great keenness to conclude that no honest men were in the habit of occupying the place.” Curious, and perhaps offended at the thought of sinister doings on his patch, Pinkerton decided to investigate. He returned again and again over the next few days, hoping to catch sight of the visitors. One evening, hearing a splash of oars as a small boat rowed out of the darkness, Pinkerton hid himself in a stand of tall grass and watched as several men scrambled ashore and lit a fire. After hearing a few snatches of conversation, Pinkerton felt sure he had uncovered a criminal hideout.

The following day, Pinkerton took his suspicions to the sheriff of Kane County. Rounding up a posse of men, Pinkerton and the sheriff led a raid on the island a few nights later and discovered an elaborate counterfeiting ring. “I led the officers who captured the entire gang,” Pinkerton reported proudly, “securing their implements and a large amount of bogus coin.” The sheriff subsequently discovered that the ringleaders were well-known swindlers, or “coney men,” who were also wanted for cattle rustling and for horse theft. The episode brought Pinkerton a great deal of attention, with eager villagers stopping him in the street to hear details of the raid. “In honor of the event,” he recalled years later, “the island ever since has been known as ‘Bogus Island.’”

The matter would likely have ended there but for the arrival a short time later of the tall, well-dressed stranger. It seemed obvious to the shopkeepers Henry Hunt and Increase Bosworth that Pinkerton, the hero of Bogus Island, would be just the man to prevent another outbreak of counterfeiting. Pinkerton himself, standing barefoot in the back room of the general store, felt dubious. He had no skills, he told the two men, and no experience. “Never mind now,” one of the shopkeepers told him. “We are sure you can do work of this sort, if only you will do it.” If Pinkerton could catch the stranger in the act of passing bad paper, they insisted, the plague might be cut off at its source.

This, Pinkerton later realized, was the turning point of his career:

There I stood, a young, strong, agile, hard-working cooper, daring enough and ready for any reckless emergency which might transpire in the living of an honest life, but decidedly averse to doing something entirely out of my line, and which in all probability I would make an utter failure of. I had not been but four years in America altogether. I had had a hard time of it for the time I had been here. A great detective I would make under such circumstances, I thought.

Privately, his reservations were more practical. He could see little advantage in neglecting his cooperage for this “will-o’-the-wisp piece of business.” He wavered for a moment or two—“What do I know about counterfeiting?” he asked—but Hunt and Bosworth persisted, certain he would succeed if he put his mind to it. Pinkerton, flattered by their confidence, made an impulsive decision: “I suddenly resolved to do just that and no less,” he recalled, “although I must confess that, at that time, I had not the remotest idea how to set about the matter.”

For all his reservations, Pinkerton wasted no time. Posing as a “country gawker,” he strolled into town to strike up a conversation with the stranger, and he soon found himself invited to have a quiet chat on the outskirts of town, away from prying eyes. There, the visitor opened a cautious line of questioning, identifying himself as John Craig, a farmer from Vermont, and hinting that he needed a local partner to join him in a lucrative scheme. Not wishing to seem too eager, Pinkerton gave measured responses, admitting that times were “fearfully hard” and that he would be open to a scheme “better adapted to getting more ready cash.” All the while, Pinkerton noted, Craig studied him closely with “a pair of the keenest, coldest small gray eyes I have ever seen.” Worse yet, Pinkerton glimpsed the handles of a pair of pistols protruding from Craig’s coat. “I had nothing for self-protection,” he recalled, “save my two big fists.” As Craig continued his questioning, Pinkerton felt “a sense of insignificance” as he measured himself against the older man. “There I was, hardly more than a plodding country cooper,” he said. “I felt wholly unable to cope with this keen man of the world.”

As it turned out, however, a plodding country cooper was just what Craig wanted. Turning suddenly, the older man asked point-blank if Pinkerton had ever passed any counterfeit currency. “Yes, Mr. Craig,” Pinkerton replied promptly, “but only when I could get a first-class article. I frequently ‘work off’ the stuff in paying my men Saturday nights. Have you something really good, now?”

Craig answered that he had a “bang up article,” and passed over a pair of bogus ten-dollar bills. Pinkerton had never seen a ten-dollar bill—real or bogus—in his entire life, but for Craig’s benefit he pretended to be a shrewd judge of forgeries. “I looked at them very, very wisely,” he recalled, “and after a little expressed myself as very much pleased with them.”

Craig now made his proposal. He would sell Pinkerton five hundred dollars’ worth of phony bills for twenty-five cents on the dollar, or $125 in genuine “eastern bills.” If all went well, he would take Pinkerton on as his local partner, allowing the young cooper a chance to clear more cash in one year than Dundee’s most prosperous merchant would see in a decade. Pinkerton took a moment to weigh the offer, then put out his hand to seal the deal. The two men arranged to carry out the exchange later that day at an appropriately remote spot—an unfinished church building in nearby Elgin.

This would be the first great test of Pinkerton’s career, and he bungled it badly. As Craig rode off toward Elgin, Pinkerton headed back to Dundee to report to Hunt and Bosworth, who immediately supplied the cash needed to make the exchange, confident that Craig’s arrest and prosecution would soon follow. At the deserted church in Elgin, however, Pinkerton’s inexperience showed itself. As he passed the bundle of cash over to Craig, the older man asked him to step outside for a few minutes to see if anyone happened to be watching. Pinkerton did as directed, realizing too late that he had “placed myself in the man’s power completely” by taking his eyes off the money. A moment later, Craig reappeared, telling an absurd story: A shadowy colleague had swooped in unexpectedly, he claimed, and left a mysterious parcel behind. “He is never seen by any living person with whom I have business,” Craig insisted. “Look under that stone over yonder. I think you will find what you bought.” Pinkerton saw at once that he had been badly outmaneuvered. Craig had arranged matters so that he could not be apprehended in possession of incriminating evidence. Reaching down, Pinkerton took the parcel from under the stone and found fifty ten-dollar bills inside. Glancing at Craig, Pinkerton saw a steely, self-satisfied expression on the older man’s face. “Old John Craig is never caught napping, young man,” he said pointedly.

Pinkerton hesitated for a moment, badly unsettled, as Craig continued to study him carefully. Recovering himself, Pinkerton saw that he had no choice but to continue playing his role, in the hope that the situation might yet be turned to his advantage. Thumbing through the packet of bills, he asked Craig how much more of his “product” happened to be available. The counterfeiter hedged, but he allowed as how he might be able to get his hands on an additional four thousand dollars. Pinkerton leapt at the opening. “Look here, Craig,” he said, “if you wouldn’t be in too big a hurry about getting back home, I’ll tell you what I’ll do. I believe I could make arrangements to buy you out altogether.” Clutching the forged notes, Pinkerton hastily improvised a plan. If Craig would allow him a few days to gather up the necessary “eastern bills” from friends in the area, Pinkerton would meet him in Chicago, at a hotel called the Sauganash, to make the exchange. After a moment’s consideration, Craig agreed. In the meantime, he said, he would lay low at the home of a friend. “Good-bye, then,” said Craig shaking Pinkerton’s hand. “But, mind you, be discreet!”

Being discreet was now the least of Pinkerton’s problems. He had, in effect, made an all-or-nothing bet on the integrity of a counterfeiter. If Craig were to have second thoughts, or receive a better offer, Pinkerton would have nothing to show for Hunt and Bosworth’s money but a pile of worthless paper. Even so, as the two men parted ways, some previously untapped instinct told Pinkerton that Craig could be trusted to keep their bargain: “Criminal though he was, he was a man who, when he had passed his word, would be certain to keep it.”

Returning to Dundee, Pinkerton found that Hunt and Bosworth did not share this opinion. Craig had ridden off with a great deal of their money in his saddlebags and they feared that he “would leave us all in the lurch.” Shaken by their doubts, Pinkerton went to bed that night filled with dread, “and fully satisfied in my own mind that I was not born to become a detective.”

By the following morning, however, he had formed a plan of action. For three days, he devoted “very little attention to my casks and barrels” and gave himself over entirely to “a good deal of nervous plotting and planning.” Having learned a bitter lesson at the church in Elgin, Pinkerton anticipated that Craig would arrange matters in Chicago so that no incriminating bills would be found in his hands. “Circumstances and my own youth and inexperience were against me,” Pinkerton admitted, but he was determined to atone for his earlier failure. At last, on the appointed day, Pinkerton saddled a horse and rode into Chicago.

The Sauganash, Chicago’s first hotel, was a whitewashed log structure at Wolf Point, where the main stem of the Chicago River divides into its north and south branches. Described by one early visitor as a “vile two-storied barrack,” the Sauganash featured a tavern on the ground floor, where traders and other visitors were known to gather. Arriving well ahead of time, Pinkerton made a few final arrangements with a pair of Chicago constables. He positioned one of the officers inside the tavern, where the meeting was to take place, while the second would keep watch outside the building for any unexpected arrivals or departures. Satisfied, Pinkerton took a seat in the hotel’s front room and waited.

At the appointed hour, John Craig entered the room and “sauntered about for a time,” apparently in no rush to acknowledge Pinkerton. Finally, he snatched up a newspaper and dropped into an adjacent seat, pretending to be absorbed in reading. Without taking his eyes off the paper, he asked in a lowered voice if Pinkerton had managed to bring the money. Pinkerton, keeping his eyes fixed straight ahead, acknowledged that he had. Craig instructed him to pass it over, promising that a package of bills would be in his hands “in the course of an hour.” Pinkerton was ready for this. Drawing a deep breath, he said that the friend who had loaned him the money, a man named Boyd, was having second thoughts. Boyd insisted on seeing the merchandise in advance, Pinkerton explained, and had accompanied him to Chicago in order to supervise the transaction. In fact, Pinkerton said, he expected Boyd to appear at any moment. The man was a lawyer, and a “stickler for form.”

Craig appeared deeply unsettled by this development. He insisted “with some warmth” that he did not want an outsider complicating matters. Pinkerton answered in a tone that suggested the matter was out of his hands. “You know I would trust you with ten times this sum,” he said, “but I’ve placed myself in this damned lawyer’s power, and he insists like an idiot on having the thing done only in one way.”

As Craig’s objections mounted, Pinkerton admitted to himself that his chances of success were now “beginning to look a little misty.” The two men adjourned to the hotel’s tavern, where Craig knocked back a fortifying drink as Pinkerton continued to plead his case. After a few moments, Craig took himself off to consider the matter in private. Pinkerton later learned, from the constable posted outside, that the older man passed the next half hour walking aimlessly in various directions, making sudden stops and turns, and looking frequently over his shoulder to see if he was being followed. After a time, he drew up short, as though he had come to an abrupt decision, and made his way back to the hotel.

Seeing Craig reappear in the hotel’s front room, Pinkerton at once stepped forward. “Well, Craig, are you going to let me have the money?” he asked. The older man looked back at him with an air of polite surprise, as if Pinkerton were a total stranger.

“What money?” Craig asked.

Pinkerton hadn’t expected this. At a stroke, all his careful planning appeared to be undone. “The money you promised me,” he stammered.

Craig remained unflappable. “I haven’t the honor of your acquaintance, sir,” he said coolly, “and therefore cannot imagine to what you allude.”

Pinkerton was utterly dumbfounded. “If the Sauganash Hotel had fallen upon me,” he would later say, “I could not have been more surprised.”

Staggered as he was, Pinkerton knew that he had to take action. His entire scheme depended on apprehending Craig in the act of selling the forged bills. Now, with the older man feigning ignorance of Pinkerton and his designs, the would-be detective had no evidence that would stand up in court. Craig, he knew, was far too slippery to allow himself to be apprehended with counterfeit money in his pockets. If the case came before a judge, it would come down to one man’s word against another’s. The situation appeared hopeless, but Pinkerton felt obligated to follow through with his plans. Otherwise, Craig would simply slip away and return to his home in Vermont, out of the jurisdiction of the local authorities, carrying Hunt and Bosworth’s money off with him.

“There was only one thing to do,” Pinkerton concluded, “and that was to make Mr. Craig my prisoner.” Pinkerton signaled the constable across the room, who hurried over to make the arrest. Craig, still pretending ignorance of both Pinkerton and his accusations, loudly protested his innocence. A large crowd gathered, and “considerable sympathy was expressed for the stately, gray-haired man who was being borne into captivity by the green-looking countryman cooper from Dundee.” Pinkerton’s first big case—which he would one day recount under the heading of “How I Became a Detective”—ended with a swarm of bystanders raining insults on his head.

As it happened, Pinkerton’s flimsy evidence was never tested in court. Although Craig was duly arrested and locked up to await trial, it was discovered one morning that he had mysteriously vanished from his jail cell—leaving, it was said, at least one jailer considerably richer. The episode taught Pinkerton a valuable lesson in what he would call “the perfidy of officials.” A second, more personal lesson had already been taken to heart. Writing of the episode many years later, Pinkerton reflected on a moment at the church in Elgin when he found himself lingering over Craig’s bundle of fifty ten-dollar bills: “For a moment the greatest temptation of my life swept over me,” he admitted. “A thousand thoughts of sudden wealth and a life free from the grinding labor which I had always known, came rushing into my mind. Here in my hands were five hundred dollars, or what professed to be, every one of them as good as gold, if I only chose to use it.” He would resist the temptation, but Pinkerton never forgot it. Throughout his career, he claimed that he could never look on those who had fallen prey to greedy impulses without “a touch of genuine human sympathy.”

Returning to Dundee, Pinkerton found that his latest exploit brought him even more notice than the Bogus Island adventure. “The country being new, and great sensations scarce, the affair was in everybody’s mouth,” he wrote, “and I suddenly found myself called upon, from every quarter, to undertake matters requiring detective skill.” Before long, Pinkerton was offered the post of deputy sheriff of Kane County. The duties were not terribly demanding, mostly serving court papers and chasing down an occasional horse thief, but his days as a country cooper were coming to an end—“all of which,” he later admitted, “I owe to Old John Craig.”

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