Chapter 17

Crime Pays

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WAYNE WHEELER RARELY had much trouble with congressional committees. When he wanted a change in the law—the banning of medicinal beer, say, or tougher penalties—he could count on one of his Capitol Hill allies to serve up a hearing custom made for a Wheeler star turn. When those hearings were momentarily seized by a wet representative or senator trying to pillory Wheeler and the ASL, he still managed to perform with poise. By nature a polite and cordial man, at times even jovial, he was as cool under pressure as he was hot when applying it. He didn’t even complain in 1922 when Representative George Tinkham, a big-game hunter from Massachusetts, tried to mount Wheeler’s head on his wall.

The superwet Tinkham, who once said he considered Wheeler’s “very presence in the Capitol an offense against decency,” compelled him during a committee hearing to read aloud a lengthy list of wet political committees, by way of demonstrating the alleged breadth of opposition to Prohibition. Wheeler could have been reciting a school honor roll as he tripped amiably through the list: “The American Liberties League . . . the Constitutional Liberty League . . . the Light Wine and Beer League of America . . . the National Order of Camels . . .”—no explanation asked, none given—“the Self Determination League of Liberties . . . the Sanity League of America . . . the Auxiliary of Caravans for Women, Order of Camels . . .” It was likely that some of these groups had fewer members than syllables in their names. When the hearing concluded, Wheeler noted that portions of the proceedings were hardly germane. But, he said, he had wanted to demonstrate his willingness to cooperate.

Wheeler’s adroit manipulation of congressional opponents finally failed him in April 1926. A subcommittee of the Senate Judiciary Committee convened that month ostensibly to consider various amendments to the Volstead Act. No one believed that was its actual mission. For one thing, the likelihood of any moderating amendment getting through the still-dry Senate was nil. For another, one of the five members of the subcommittee was H. L. Mencken’s “supreme artist of assault,” the ungovernable James A. Reed of Missouri, who treated his political enemies as if they were fish he had landed. He’d inflict as much pain as he could as he yanked out the hook.

Back when Reed compared Andrew Volstead to “the burners of witches,” he had won the unprecedented censure of the House of Representatives (by a vote of 181–3). Reed loathed the League of Nations, despised woman suffrage, and detested the “snooping spinsters” who supported federal aid to state maternity programs. Oswald Garrison Villard, editor of the Nation, said, “No other public man has such a mastery of bitter sarcasm, or is a better hater” than Jim Reed. If there was anyone in public life Reed hated more than Wayne Wheeler, he managed to keep it a secret.

In the 1926 hearings the “truculent Senior Senator from Missouri,” said the New Republic, “assumed with his usual lordly manner the real leadership of the wet cause in Washington.” As a member of the Senate’s Democratic minority, Reed did not control the subcommittee’s gavel, but he nonetheless dominated the hearings, which the New York Times called “a war of words as bitter as any Washington has known in a generation.” Over three long weeks of testimony he elbowed aside the other subcommittee members, all of them drys. At times Reed demonstrated why he was called “the Bellowing Bull of Missouri”; at other moments he filleted dry witnesses with a stiletto; and when friendly wets stepped up to testify, he displayed the manners of a maitre d’, presented with the charm of your favorite uncle.

The wet witnesses and their sympathizers took the stage first. The opening lines of this tightly scripted drama were delivered by Senator William Cabell Bruce of Maryland, who would soon celebrate the marriage of his son David to Andrew Mellon’s daughter Ailsa at a lavish and evidently dry reception. (This might have been why Bruce called Prohibition “a blight upon the entire joyous side of human existence.”) But he had more practical reasons for opposing it as well: most of the $443,839,544.98 in liquor tax revenues the federal government had collected in the last fully wet year, he said, was now going into “the pockets of foreign and domestic lawbreakers.” Reed gave a great deal of time to the testimony of Emory Buckner, whose criticism of the underfunded and ill-designed federal enforcement effort was both informed and eloquent, and he welcomed twenty congressmen from New York City, Albany, and Buffalo who dropped by en masse from the opposite wing of the Capitol Building to condemn the ASL and make the case for the legalization of light wines and beer.

The wide berth Reed gave wet witnesses turned claustrophobic when it came time to hear the parade of drys summoned by his colleagues. When Patrick H. Callahan, a varnish manufacturer from Louisville, stepped forward in behalf of the Association of Catholics Favoring Prohibition, Reed made certain to find out how many members the organization had (320) and how that compared to the number of Catholics in the United States (an abashed Callahan was forced to admit there were something between eighteen and twenty million). The unprepossessing Fred T. Smith, chairman of something called the Citizens’ Committee of 1000 for Law Enforcement, hardly fared better. Pressed by Reed to state his occupation, Smith said, “I preach law enforcement and patriotism and religion up and down the country, and sell asbestos when I have a little extra time.”

Reed pushed dry witnesses as if they were playthings and pulled them as if they were taffy, taking so much time with his questions, his badgering interjections, and his own speechifying that the briefly rebellious majority members of the committee voted to grant the drys extra time because Reed had consumed so much of it. Bishop Cannon, Ella Boole of the WCTU, a black woman named Marie Madre-Marshall “representing,” said another dry witness, “the 15 million colored people who have suffered from lack of enforcement”—for seven long days the drys took their places at the witness table to offer their fervid testimony, to endure Reed’s unrelenting inquisition, and, happily or not, to adorn the front pages of newspapers across the nation. Each morning crowds lined up hours before the hearing room opened; the small portion that managed to squeeze in—maybe a third of those waiting—were treated to the Jim Reed Show, which they watched either in strangled horror or with unchecked awe. The only light moment came when Reed, his blue-gray eyes wide with theatrical innocence, asserted that he himself was impartial and only trying to find out the facts. The anxious and tired crowd exploded in tension-relieving laughter. Reed immediately reached for the acid; their outburst, he said, was “the laughter of fanatics and fools.”

The hearings, said the Times, were “the all-absorbing topic of comment and debate” throughout Washington. By the time the third week began, the coming confrontation between Jim Reed and Wayne Wheeler was anticipated in drawing rooms and on street corners, a heavyweight contest with more explosive potential than any battle the Prohibition debate had produced. Wheeler had been taking his place in the front row of the audience every day, to provide support for his fellow drys and also because Reed refused to let him know on what day he might be asked to testify. Wheeler was not well in the spring of 1926; doctors had diagnosed chronic heart trouble, he told a colleague, caused by “long years of overdraft on my reserve force.” When the committee was not in session, he remained in bed at his apartment near the National Zoo. He “looked like a corpse,” a colleague would recall, “haggard, weary, and spent.”

Finally, on a Saturday that the Times expected to culminate in “a spectacular war of words between Mr. Wheeler and Sen. Reed,” the last half of the last scheduled day of hearings arrived. By then the committee had spent fifteen days taking more than 1,400 pages of testimony from 133 witnesses. It was shortly after the lunchtime recess when Wheeler finally settled in his chair at the witness table and began to read his prepared remarks. He took most of an hour to present his rebuttal of the wet witnesses. He attacked the unfaithful Emory Buckner, he challenged the licentious pro-beer congressmen, and he defended a federal police apparatus that had been assaulted by several witnesses who were part of that apparatus. Crime may have been rampant, and illegal liquor may have been everywhere—Wheeler could hardly deny it. But that did not mean he lacked an explanation. In one sentence near the end of his speech he alit upon a formulation on which one could have balanced the entire war between the wets and the drys. “The very fact that the law is difficult to enforce,” said Wayne B. Wheeler, “is the clearest proof of the need of its existence.”

At least he didn’t have to endure much in the way of questions. Jim Reed had not bothered to come back after lunch.

REFLECTING ON THE two years he had spent teaching school back in the 1880s, Wayne Wheeler once said, “No one can hold the confidence of his pupils or associates who cannot keep a smiling exterior, no matter how disturbed he is inside.” Reed had scratched Wheeler’s smiling exterior and disturbed his insides so severely that he traveled to Battle Creek for a three-week rest cure as soon as the hearings ended. His friend Dr. Kellogg prescribed green vegetables, fig bran, and three or four enemas a week at bedtime. Wheeler was wary when he returned to Washington and told Scott McBride it had proved impossible to “overdraw on [my] health account for twenty years and get it back in [just] twenty days.”

Jim Reed, of course, couldn’t have felt better. Writing in 1943, the dry publicist Ernest Gordon described the critical impact of the hearings: they “gave the impression that Prohibition,” for the first time since its enactment, “was not a settled question.” That may not have been Reed’s primary intention—he doubtless would have been gratified simply for having inflicted punishment and provoked humiliation—but there was no question that he had turned Prohibition, six years into its dominion, from a fact into a debate. It was a change of circumstance so delightful he immediately hopped aboard another Senate committee, this one investigating campaign spending, and zeroed in on the finances of the ASL and other dry groups.

Reed’s most gleeful moment in these proceedings may have come when he forced one of Gifford Pinchot’s advisors, whose salary was paid by the Pennsylvania WCTU, to admit that the governor’s WCTU-funded field agents were each spending eight to ten dollars a day on drinks while gathering evidence—all the more impressive when you consider that a shot of rye in a Philadelphia speakeasy went for just fifty cents. But that was sideshow. The earlier hearings had altered the rules of engagement between wet and dry. Where the discussion had previously concerned the evils of alcohol, the Reed Committee forced a change of subject. At issue was not the law itself, or the reasons for the law, but what the drys insisted was the enforcement of the law. Ten years earlier, “submission”—as in, submission to the states for ratification—had been the euphemism congressional drys had used in place of the scarier “Prohibition.” Now “enforcement,” or in formal usage “law enforcement,” became the stand-in for the real issue that propelled the Prohibition wars: who would control the country, the wets or the drys?

From the dry perspective, the power of the enforcement trope lay in its incontrovertibility: who could be against law enforcement? This was especially the case as the criminal activity that had blossomed at Prohibition’s dawn—largely local, infrequently violent—multiplied in scale and in carnage. It wasn’t as if the police sirens and the tommy guns hadn’t sounded before 1926; the New York Times wrote about the new-style gangster as early as 1923 (“He shoots from ambush, and preferably at backs”), and in 1924 Senator Frank L. Greene of Vermont was severely wounded in a crossfire between Prohibition agents and bootleggers just blocks from the Capitol Building. But by mid-decade the trials of George Remus and, later, “Big Bill” Dwyer—the New York bootlegger who claimed Emory Buckner had almost convinced him of his guilt—revealed criminal operations of a size and sophistication Americans had never known.* And as often as the drys used the rise of organized crime to underscore the need for Prohibition, the wets used it to demonstrate Prohibition’s failure.

It was true that criminal activity had been “organized” before Prohibition; in 1919 Henry B. Chamberlin, director of the Chicago Crime Commission, noted that “modern crime, like modern business, is tending toward centralization, organization, and commercialization.” But Prohibition offered a graduate course for training in the crime industry. John Torrio, originally from Brooklyn, began to bring Chicago mobsters into the illegal liquor business on a large scale (with the assistance of another Brooklyn import, twenty-year-old Al Capone). Until then the Torrio operation had largely devoted its organizational skills to running gambling operations and brothels, many of whose managerial requirements—servicing a wide range of locations, handling large sums of money, seeing to the safety of one’s allies and the discomfort of one’s foes—were identical to those required by the booze trade.

But those earlier businesses had not required the transportation and distribution networks that would make crime not only organized but interregional. First, Torrio, Capone, and similar entrepreneurs across the country needed vehicles. In New York, Meyer Lansky launched his bootlegging business from the car and truck rental operation he ran from a garage underneath the Williamsburg Bridge. Once the mobsters had wheels, they still had to build alliances with confederates in distant cities. Chicago’s supply of Canadian whiskey arrived courtesy of the efficient forwarding services of Detroit’s Purple Gang. Boo Boo Hoff needed western associates to unload and distribute the goods he shipped by rail from Philadelphia to St. Louis and St. Paul. Moe Dalitz’s operation in Cleveland, using planes as well as boats, ferried Bronfman liquor across Lake Erie—“the Jewish lake,” bootleggers called it—and distributed it through a network that included various Ohio and Pennsylvania affiliates, as well as Lansky’s New York operation. After internecine warfare and a more effective Coast Guard crippled Rum Row, Massachusetts had to get its liquor via an eight-hundred-mile overland corridor from Detroit. During his Mobile investigations, Hugo Black established that the city’s bootleggers had business relationships with mobsters in Detroit and Chicago.

These alliances were the first manifestations of a crime syndicate operating on a national scale. In time they became the foundation of multilateral “peace conferences,” such as the 1929 meeting in the Hotel President in Atlantic City, when mobsters from Chicago, Cleveland, Philadelphia, Newark, and New York granted each other territorial exclusivity, enabling them to operate unencumbered in their respective cities. Eventually this sort of arrangement would harden into formal partnerships, such as the cartel established by Lansky and his fellow New Yorker Lucky Luciano, Abner “Longy” Zwillman of Newark, Charles “King” Solomon of Boston, Daniel Walsh of Providence, and a few others who together would control the entire bootleg business from Boston to Philadelphia. They fixed prices throughout their territory, struck an exclusive distribution deal with their Canadian suppliers, and rewarded John Torrio for brokering the arrangement by granting him a fungible inventory of five thousand cases of liquor a month.

Most of the actors on this lucrative stage were young men who had seen opportunity and grabbed it. By 1926 Lansky, already running his “most efficient international shipping business in the world,” was only twenty-four years old. The elegant Longy Zwillman, who eventually would sell his legal post-Repeal distribution business to his pre-Repeal trading partner Sam Bronfman for $7.5 million, was either twenty-two, twenty-three, or twenty-seven, depending on which of his birth certificates you consulted. Luciano was twenty-seven, and so was Capone. The image of Capone refracted through decades of popular culture gets jarred somewhat when his age is factored in: he was only twenty-five when he took over Chicago from his mentor Torrio, was fundamentally gone from the city before he turned thirty, and when he emerged from his eventual prison sentence a syphilitic wreck, he was only forty.

Despite their youth, their ghetto origins, and the fact that they were by any measure engaged in criminal activities, an odd respectability accrued to many of these mobsters. In some places their ethnic loyalties and their hatred of dry vigilantes led them to take part in anti–Ku Klux Klan campaigns. They also acquired a certain glamour from their involvement in the entertainment industry; Longy Zwillman had a very public romance with Jean Harlow, and several big-time mobsters owned popular nightclubs. The New York thug Owney Madden (whose romance with Mae West led her to describe him as “sweet, but oh so vicious”) opened the Cotton Club in a nightspot he had taken over while serving a manslaughter sentence in Sing Sing.

Capone was especially mindful of his public image. Thanks to newspapermen who were either amused or seduced by his accessibility, Chicagoans knew that Capone extended charity to the poor and shared his house on South Prairie Avenue with his siblings and his widowed mother. When Chicago got too hot for him and he sought repose in Miami Beach, Capone announced that he intended to join the Rotary Club. Some might have disputed his description of himself as a “public benefactor,” but few could have disagreed when he said, “I give the public what the public wants. I never had to send out high pressure salesmen. Why, I could never meet the demand.” He had a point: if you separated the customer service aspect of the bootlegging business from the other pastimes that engaged the mobsters, they could seem about as criminal as a group of jaywalkers. The bootleggers, wrote historian Mark H. Haller, “had customers, not victims.” Whoremongers brutalized the women who worked for them, and numbers racketeers and gambling house operators took an extortionate cut off the top, but except when they were pouring colored industrial alcohol into Haig & Haig bottles, the bootleggers gave their customers exactly what they wanted, at a price no one was forced to pay.

The money to be made by violating the Eighteenth Amendment’s proscriptions against the sale, manufacture, and transport of intoxicating liquors was spectacular. Emory Buckner believed annual sales of bootleg liquor had reached $3.6 billion nationally by 1926. By way of comparison, that was almost precisely the same as the entire federal budget that year—army, navy, and every other government function included. In 1925 the Bureau of Printing and Engraving printed nearly $300 million more in large-denomination bills than it had in 1920. “What honest businessman deals in $10,000 bills?” Fiorello La Guardia asked the Reed Committee. “Surely these bills were not used to pay the salaries of ministers.” Instead, the abundant cash bought armor-plated automobiles (Capone’s cost the 2009 equivalent of $350,000), solid silver toilet seats (that was the prize possession of Chicago bootlegger Terry Druggan), and, by the truckload, cops and politicians and judges.

Political corruption had been baked into the system almost from the beginning. Early Prohibition directors for New York and Pennsylvania—a judge and a state senator, respectively—were under indictment within a year of assuming their jobs. On the very day that the director for the Ohio region, former congressman Joshua E. Russell, was telling an audience at the Sidney Baptist Church that “we are now engaged in a struggle with the forces of lawlessness in an effort to sustain the majesty of the law,” he and his top aide were in the process of diverting 22,416 gallons of alcohol from a distillery in Troy, Ohio.

Russell served two years in prison for his crimes. So did John W. Langley, a bone-dry congressman of expansive girth and melodious diction who was known in his eastern Kentucky district as either “Promissory John” or “Pork Barrel John,” for the vows he made to his constituents and for his ability to fulfill them. On a congressman’s annual salary of $7,500, Langley managed to deposit $115,000 in his bank account over a three-year period in exchange for arranging the release of a million gallons of “medicinal” liquor to New York–based bootleggers. He was reelected despite his conviction; then, after losing his appeal and entering prison, his wife was twice elected in his place.

Yet even if the stench of corruption did not linger around some of the politicians who extracted profit from Prohibition—a man who delivered jobs, projects, and pork to his district could be forgiven much—their coconspirators came from a shadowland filled with nightmares for dry and wet alike. The cash that went into the bank account of a popular politician was easily ignored by complacent voters, but the liquor money cascading through the bootlegging industry and into the hands of mobsters—all of it untaxed, of course—also underwrote the expansion of associated rackets like gambling and loan-sharking; created opportunities for new ones, like money laundering; and funded escalating arms races whenever treaties crafted by criminals (you take the north side, I’ll take the south) broke down and gave way to intramural gang wars.

Unable to turn to civil authorities to settle disputes, the mobsters had to find other means of conflict resolution. Seattle bootleggers sought to forestall discord when they convened in a ballroom at the New Washington Hotel in 1922; operating under Robert’s Rules of Order, they fashioned an agreement to set prices and establish other forms of self-regulation (no doubt impressing an out-of-town associate, Sam Bronfman, who had dropped in on the meeting). In Philadelphia, conflicts between rival gangs were arbitrated in a netherworld one of the local papers called “Racketville,” a sort of parallel City of Brotherly Hoodlums with its own mob-selected judges, lawyers, and others “rendering decisions which [its] vassals must obey without question.”

But in most cities such civilized proceedings were unknown. The warfare that led to 215 mob killings in Chicago in one three-year period was a direct by-product of broken contracts that did not lend themselves to polite resolution. Clarence Darrow, who despised Prohibition (and was known to represent the occasional indicted bootlegger), gave the best explanation of the bootleggers’ dilemma. “The business pays very well,” Darrow said, “but it is outside the law and they can’t go to court, like shoe dealers or real-estate men or grocers when they think an injustice has been done them, or unfair competition has arisen in their territory.

“So,” Darrow concluded, “they naturally shoot.”

SOME HISTORIANS ARGUE that our sense of epidemic violence in the 1920s is a distortion fostered by Hollywood. In fact, it did increase by quite a bit, from slightly less than twelve murders or assaults per hundred thousand population in 1920 to sixteen in Prohibition’s last year, 1933 (and then subsided to fewer than ten by 1940). But if you had been reading the newspapers of the age, you might have felt the rise in violence was even steeper. When Prohibition was inching toward birth in the summer of 1919, an institution that would grow stronger with every bloody manifestation of the liquor wars also came into being: the American tabloid press, born with the launch of the New York Daily News. Seeking to build readership on the trail of bodies that Prohibition left in its wake, “the newspapers began talking about [gangsters’] hiring of torpedoes, trigger men, gorillas, and rods,” wrote lexicographer Stuart Berg Flexner, and “their use of pineapples . . . and Tommy guns.” Bishop Cannon condemned the press for “the sewage which pours into our homes almost daily from the[ir] columns.” But you could move a lot of papers when the front page was painted with gun battles, sordid deaths, and mob funerals like the one that sent off Brooklyn gangster Frankie Yale. Laid out in a $15,000 silver coffin, accompanied by a cortege of more than two hundred limousines (thirty-eight of them packed with flower arrangements), and guarded by a hundred city cops, Yale starred on front pages all the way to California.

Although the papers made celebrities out of the gangsters, they did not fail to suggest the causal relationship of the Prohibition laws and the bloodshed, not least because wet papers realized that linking the Volstead Act to murderous violence could help the wet cause.* This wasn’t hard to do: from the assassination of Dion O’Banion in his Chicago flower shop in 1924 through the St. Valentine’s Day Massacre five years later, the most famous killings of the era were ignited by alcohol. With 3.6 billion untaxed dollars at stake, how could it be otherwise? Owney Madden once said, “I like an investment where you can put your money in this week and pull it out double next week, or the next.” To secure a cash flow like that, murder could seem like bookkeeping—just another thing you had to do to keep your business on track.

ON FRONT STREET in New Bedford, Massachusetts, you didn’t have to go far to find entertainment in the early 1920s. Out in the harbor most mornings, a small fleet of motorboats buzzed and roared from Pope’s Island to Fort Phoenix and back. They may have looked like bees roused from a hive, but on some days they made a sound that suggested some sort of nautical Armageddon. That was because many of the boats were equipped with full-throated Liberty V-12 engines that you could buy from the federal government for one hundred dollars each, delivered in their original crates. A few years earlier, the four-hundred-horsepower Libertys had powered American military aircraft; now, converted to maritime use by the speedboat racer Gar Wood and other entrepreneurs, the Libertys that had been on the assembly lines when the war ended had become the sine qua non of the rum-running fleet.

As the New Bedford rumrunners prepared to put on their daily harbor show, you could walk along the wharves and see them engaged in congenial conversation with Coast Guard officers. One local boy recalled a guardsman bumming a cigarette from a former fisherman. “Thanks, Charlie. See you tonight,” the guardsman said. The rumrunner replied affably, “Not if I can help it.” This was characteristic of the early days of Rum Row, just as it would have been in western border towns, or on the waterfront in Windsor, Ontario, or in the woods of northern New England. “We knew the officers and they knew us,” a Vermont bootlegger told an interviewer. “You know, the same as you know football players on another team, something like that.”

But by mid-decade the value of the goods afloat on American coastal waters had brought a vicious element into the rum-running business: nautical auxiliaries of the violent urban gangs. For crewmen on the mother ships, the days when your customers would bring you groceries or carry your mail ashore had given way to fear-filled nights. The sanguinary chill that settled over Rum Row had been signaled by the scuttling, in 1923, of the John Dwight, a 107-foot steam trawler hauling a Canadian cargo of Frontenac Export Ale (“Contains all the alcohol needed for long sea travel,” the label read) through “Rum Lane,” near Martha’s Vineyard. The bodies of eight Dwight crewmen were later found in the surf off the Vineyard hamlet of Menemsha. Three had had the skin stripped from their faces. Others had had their eyes burned out, their fingerprints scarred beyond recognition by acid. The son of the Dwight’s captain was found adrift in a dinghy, his skull fractured, his body wedged beneath a seat. One of the dead men was known to have been carrying $100,000 in cash for an impending purchase.

From the earliest days of Rum Row, there had been the threat of hijackers looking to commandeer a boat and seize its cargo. But a duffle filled with bills was much easier to handle than a hold jammed with beer, so the early breed of seagoing thieves was soon supplanted by men like those who ravaged the John Dwight, predators more interested in cash than in cargo. These pirates, known in the trade as “go-through guys,” needed to have decent intelligence sources—disloyal crewmen were prime informants—but beyond that they required only a small boat, a few weapons, and murderous intent.

In time these freebooters were themselves put out of business by the big syndicates, which were savvy enough to remove cash from the equation and powerful enough to scare off freelancing pirates. Contracts were consummated when the captain of the cargo ship and the men receiving the goods on shore could match the halves of a dollar bill that had been torn in two by their respective employers. “Rum running has altered almost unbelievably,” reported the New York Times in late 1924. “The rules are changed. The amateur is no more.”

Given the congenital ineffectiveness of the federal enforcement effort, the big-time smugglers could not have been prepared for the government response to the professionalization of Rum Row: for virtually the only time in the fourteen-year Age of Volstead, federal officials rose to the enforcement challenge. The fleet of fifty-five seaworthy vessels the Coast Guard had had at the beginning of Prohibition had grown somewhat, but was as able to cover 5,000 miles of saltwater coastline, plus another 1,450 miles of shoreline along the Great Lakes and the St. Lawrence River, about as effectively as a napkin could cover Nebraska. Calvin Coolidge’s unexpected request for additional funds reflected how grave the situation was. Heeding the words of the Coast Guard’s founder—the original Guard, Alexander Hamilton had said, was meant to be a “show of force” directed at “the fraudulent few”—Coolidge suppressed his chronic parsimony and asked Congress for a supplemental appropriation of $14 million to expand and modernize the fleet. Heeding the words of Wayne Wheeler (the boats of Rum Row, he wrote, had been conducting “a practical attack on our sovereignty” by “shooting actual holes in our Constitution”), Congress obliged.

Soon four thousand new guardsmen that Wheeler characterized as “incorruptible” were assigned to twenty reconditioned destroyers and three hundred brand-new small craft. Within months the beefed up “Dry Navy” seized three British rum-running boats in international waters in the North Atlantic, and scores of smaller vessels were apprehended and impounded up and down the Atlantic and Pacific coasts, along the Gulf of Mexico, and in the Great Lakes. In May 1925 an operation that became known as the “Great Offensive” dislodged fifty mother ships from the section of Rum Row that ran from Block Island to Brooklyn. And on the West Coast, what might have been the single most successful bootlegging operation in the nation foundered on the shoals of a new law enforcement technique called wiretapping.

But in the end, additional expenditures and focused effort were not enough. Except for wiretapping, each of these developments turned out to be less effective than it had first appeared. (This should not have been a surprise; even the twelve-mile limit extracted from the British through strenuous negotiation had not worked out, for it required the Coast Guard to patrol a vastly increased area.) Most of the ships chased away from Rum Row retreated to Canada, where their suppliers were led to devise new ways of getting their product to the U.S. market—chiefly, in the case of the Bronfman brothers, by the much more efficient shipment of goods by train through Ontario and across the river to Detroit (or, as Sam Bronfman always called it, “the Windsor market”). The seizure of the three British rumrunners provoked a new outbreak of diplomatic friction with the United Kingdom. Most of the impounded inshore boats, sold at government auction after the conclusion of legal proceedings, were simply repurchased by their original owners, who were usually the only bidders, as if by tacit agreement among the rum-running syndicates. In a single year the steamer Underwriter was seized four times, auctioned four times, and returned four times to its role as a rumrunner at the eastern end of Long Island Sound.

The four thousand new uniformed seamen in the Coast Guard, who were working for thirty-six dollars a month plus room and board, found it difficult (if not pointless) to remain incorruptible, and the newspapers were awash in reports of misdeeds, court-martial, and convictions. In 1928 the secretary of the Elks Lodge in Niagara Falls, New York, who had no liquor in his possession and no previous record, was fatally shot through the head after he was apprehended by a Coast Guard crew. “I would not have shot him, and probably you would not,” said a philosophical Seymour Lowman, the assistant secretary of the Treasury ultimately responsible for Prohibition enforcement, “but you want to recollect that the men engaged as Coast Guardsmen there are not college professors or lawyers.”

Even the well-funded development of the Guard’s swift new boats miscarried. Required to make its specifications available to any boatyard interested in bidding on the construction contracts, the government was effectively providing blueprints to the rumrunners, who paid the very same boatbuilders to design vessels that could outrun the ones they were building for the Guard. The Freeport Point Boatyard on the south shore of Long Island built fifteen vessels for the Coast Guard and thirty for the rumrunners they were supposed to chase down, including a trio of forty-two-foot boats for the notorious bootlegger Dutch Schultz, each one equipped with three Packard Liberator 500-horsepower air-cooled engines, bulletproof gas tanks, and room for 600 cases of liquor. On a larger scale, by 1930 a 150-foot blockade runner equipped with diesel engines, Maxim silencers, shortwave radio, armor plating, and a capacity of 8,000 cases could be had for $100,000. At a gross profit of $1 per bottle, any self-respecting bootlegger could have made back virtually his entire investment on a single run.

Just as World War I had accelerated the evolution of airplane technology, the battle between the rumrunners and the Coast Guard provoked the rapid development of powerboat design. The motorized version of the nimble Jersey Sea Skiff, with a nearly flat hull that enabled it to run its payload right up on shore, was a Prohibition product. When the New Orleans levees were breached during the Great Mississippi Flood of 1927, the first rescue boats on the scene were the exceptionally speedy craft developed for, and operated by, upriver bootleggers.

Rumrunners also copied the design of a famous boat celebrated for its speed, and according to the New York Times they intended to improve it by equipping it with machine guns. In this particular instance, the Coast Guard eventually acquired the legendary speedster by seizing it from hijackers who had been preying on rumrunners operating near Coney Island. Like its original owners, who were interested only in cash or hostages, the Coast Guard was not concerned with cargo capacity; speed was everything, and this vessel was the fastest boat in the water. Once it became government property, it was known as CG-911; before that, it had earned its reputation with a name that would in time signify thousands of boats built to a modernized version of its revolutionary, Prohibition-bred design: Cigarette.

AS THE 1920s rolled forward, accompanied by the roar of hyperthyroid speedboat engines and punctuated by the rat-a-tat of the Thompson submachine gun (during World War I it was called the “Trench Broom”; now it became known as the “Chicago Typewriter”), virtually the only good news for the party of enforcement came from an unlikely place: the United States Supreme Court.

Despite Elihu Root’s failed effort in 1920 to persuade the Court that a constitutional amendment could be unconstitutional, wets had hung their hopes for judicial sympathy on a Court that seemed genetically sympathetic to their cause. Before his appointment as an associate justice, Louis D. Brandeis had lobbied the Massachusetts legislature in behalf of the state’s breweries, and the ASL, in its maiden venture into Supreme Court politics, had actively opposed his confirmation. Justice Harlan Fiske Stone was a connoisseur of fine wines—he had a 1912 Chateau Ausone in his collection, and a 1916 Beychevelle—who had earlier tried (vainly) to move the contents of his cellar from New York to Washington when he was appointed attorney general; late in life, he would contemplate the unkind destiny that had “inflict[ed] public office and prohibition on me at one and the same time.” The court’s senior member, Oliver Wendell Holmes, was known to appreciate his whiskey (in 1927 he registered his gratitude for an illegal gift bottle with a characteristically Holmesian aphorism: “I have not forgotten the prayer ‘Lead us into temptation’ ”). And a bloc of archconservative justices led by the reactionary James C. McReynolds was instinctively aligned with James Montgomery Beck and other legal theorists who so loathed the authority of the federal government they would have strangled it had they had the chance.*

But wets hoping for a Supreme Court hostile toward Prohibition enforcement had placed most of their optimism in the capacious lap of the chief justice, former president William Howard Taft. The Anti-Saloon League loathed him (an ASL publication once referred to him as “the huge, beer-swilled Taft”). Adolphus Busch, whose personal lawyer, Charles Nagel, served in Taft’s cabinet, considered him a friend and ally (and offered Taft $50,000 a year to assume the presidency of a St. Louis bank after he left the White House). In his last month as president, Taft had vetoed the Webb-Kenyon Act and its restrictions on the interstate shipment of liquor. Congress overrode his veto, but until the Eighteenth Amendment was ratified, Taft did not moderate his views on constitutional efforts to limit alcohol consumption. Not only did he once declare Prohibition “unenforceable,” he also believed it “would put on the shoulders of the Government the duty of sweeping the doorsteps of every home in the land. If national prohibition legislation is passed, local government would be destroyed.”

Coming from a professor at Yale Law School—Taft’s home between his presidency and his appointment to the Court—this seemed a clear statement of belief, suggesting emphatic support for strong proscriptions against unreasonable search and seizure, and for the prerogatives of local authority. But Taft also believed that the citizen who obeys only laws that he endorses “is willing to govern, but not be governed”—willing, in other words, to destroy the rule of law. Consequently, Taft led a fairly stable bloc of justices who rendered a series of decisions expanding the power of the federal government, over the generally consistent objections of McReynolds and his conservative allies. Two key decisions weakened the Fifth Amendment. In 1922 the Court brushed aside the amendment’s proscription against double jeopardy, declaring that the Eighteenth Amendment’s “concurrent power to enforce” clause allowed Prohibition violators to be prosecuted in both state and federal courts for the same violation unless Congress enacted legislation barring the practice. Five years later the justices found that requiring a bootlegger to file a tax return on his illegal earnings did not infringe on the Fifth Amendment’s protection against self-incrimination.*

But it was the Fourth Amendment’s bar against unreasonable search and seizure that captured the Court’s attention most firmly, and led it, in twenty separate cases between 1920 and 1933, to a broad-strokes rewriting of a century’s worth of Supreme Court jurisprudence. The theory behind the Fourth Amendment, which dated back to the colonial era, was embedded in the primacy of the rights of the individual vis-à-vis the powers of the government, and particularly protected the sanctity of the home. During the latter part of the nineteenth century and into the twentieth, it had been judicially extended to foster the freedoms of a laissez-faire economy, shielding businessmen from raids on their premises. But once Prohibition was in place, judges realized that tight limits on searches crippled the government’s ability to enforce the Volstead Act. Long-honored restraints on police authority soon gave way. In a New York World cartoon by Rollin Kirby, a figure representing the Eighteenth Amendment was shown lynching a representation of the Fourth, with a delighted member of the ASL looking on. Defendants played an active role in this explosion of Fourth Amendment jurisprudence as well: big-time bootleggers could afford expensive lawyers who could chase a case up the judicial ladder to the Supreme Court. The Cyclopedia of Law and Practice, published in 1910, gave 15 pages to discussion of searches and seizures; its 1932 successor required 114. Eventually, half of the training classes given to new Prohibition agents were devoted strictly to search-warrant requirements and procedures. In an era when possession seemed ten-tenths of the law, cellars and suitcases and speakeasies and cars no longer appeared to be quite as sacrosanct as they once had seemed.

Especially cars. In some cities they were mobile taverns, their proprietors parking outside factory gates, peddling shots of liquor for twenty cents apiece and speeding off at the first scent of an honest Prohibition agent. As early as 1915 William Jennings Bryan had made the case that the danger of an automobile driven by an inebriated person negated the “personal liberty” argument against Prohibition—when a drunk could take to the streets behind the wheel of a powerful machine, Bryan argued, the health and safety of the driest teetotaler was placed at risk, rendering the driver’s rights irrelevant. Drunk driving in fact skyrocketed during the 1920s (in Chicago it multiplied nearly fivefold). This was accurately attributed to the steep increase in the number of cars on the road, but writing it off strictly to that was like blaming the size of an influenza epidemic on population growth. And no one disputed the role of cars in the gangster-dominated bootlegging business and the protection their operators were afforded under the Fourth Amendment. Writing to his brother Horace in 1925, Chief Justice Taft insisted that “the automobile is the greatest instrument for promoting immunity of crimes of violence . . . in the history of civilization.”

His letter to Horace was a preview of the decision the Chief Justice, speaking for the Court, would issue the next day. In Carroll v. United States, Taft dismantled a constitutional roadblock in favor of a literal one, declaring that Prohibition agents no longer needed a warrant to stop and search a car they believed to be carrying contraband liquor. One justification for this “reasonable” search: the Oldsmobile roadster in Carroll was proceeding westward from Detroit, wrote Taft, “one of the most active centers for introducing illegally into this country spirituous liquors for distribution into the interior.”

THE RUM ROW that developed along the Pacific Coast never quite grew to the size of the fleet stationed along the Atlantic seaboard and the Gulf of Mexico, nor did the traffic ever become quite as deadly. The West was much less populated than the East, of course (in 1930 there were over a million more people in New York City than in all of California), and robust domestic production in northern California kept the Coast’s thirstiest city, San Francisco, stocked with wine. But the Pacific states did have their own version of Detroit in the far Northwest, where spirituous liquors stored near the docks in Vancouver and Victoria could be shipped across the Strait of Juan de Fuca, saturate Seattle, and flow all the way down the coast to Los Angeles. The unlikely figure dominating this trade was Roy Olmstead, who became known locally as “the good bootlegger” and nationally as the appellant in what was arguably the most important and farthest-reaching Supreme Court decision that emerged from the fourteen years of Prohibition.

Olmstead had entered public life as a promising member of the Seattle Police Department, praised by the department’s very dry chief as “quick and responsive . . . bright and competent.” But Olmstead’s competence extended beyond ordinary police work, and while still a member of the department—he had been named a lieutenant when he was only thirty—he began running liquor from Canada. Roy Olmstead was handsome, personable, intelligent, and remarkably ethical. He never diluted his imports or blended them with industrial alcohol as so many other bootleggers did, and he dealt in such volume that he was able to undersell every other bootlegger in the Pacific Northwest. Historian Norman H. Clark wrote that Olmstead “avoided the sordid behavior of others in the same business—no murder, no narcotics, no rings of prostitution or gambling”—and, as a result, “many people could not regard him as an authentic criminal.” The Seattle Post-Intelligencer explained his popularity: he “served a social purpose.”

In time, Olmstead moved out of the retail business, effectively becoming wholesaler to most of the bootleggers in Greater Seattle. He established the city’s first radio station, and although Olmstead later denied it, Mabel Willebrandt believed the bedtime stories Olmstead’s wife read over the air “constituted code signals to the boats at sea, advising them when the coast was clear and where the Coast Guard boats were likely to be.” He bought a grand house in the Mount Baker section of town and socialized with the city’s leading figures, who considered him good company. Even more, they considered him useful. In the frescoed dining room of the Arctic Club, Olmstead’s services were all but invaluable.

But the Seattle office of the Prohibition Bureau was the personal property of Senator Wesley L. Jones, the very dry Senate majority whip. Determined to arrest and prosecute Olmstead, dry agents in Seattle brought in a gentleman named Richard Fryant to help build their case. Olmstead considered federal agents “too slow to catch cold,” but they were nimble enough to realize that Fryant had a practical, and novel, skill: he knew how to tap telephones. Soon the bureau had a collection of transcripts that may have read like a bad film script (“I have seen Doc and all is OK”), but nonetheless helped smother Olmstead and his associates under ninety-one separate indictments.

When he was attorney general, Harlan Fiske Stone had declared that Justice Department personnel (including members of J. Edgar Hoover’s brand-new Bureau of Investigation) were forbidden to use wiretaps, which he considered unethical. But Stone had no authority over Treasury Department personnel, including Prohibition agents, nor was his proscription enforced by his successor at justice, John G. Sargent. Still, Mabel Willebrandt, who would normally have represented the government before the Court, declared that she “thoroughly disapproved” of wiretapping tactics, and could not in good conscience argue the case. The solicitor general brought in outside counsel, and Chief Justice Taft led a 5–4 majority that found private telephone communication between two individuals no different from casual conversations overheard in a public place.

Can it be that the Constitution affords no protection against such invasions of individual security?” asked Brandeis. For the first time, the Court said it did not.

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THE LAW MADE in Olmstead v. United States stayed on the books until it was overturned in 1967, when the only dissenting vote was cast by the old Prohibition prosecutor, Justice Hugo Black. Law yet more enduring was made by Brandeis’s Olmstead dissent, in which he articulated a constitutional “right to be let alone”—words invoked by the majority nearly half a century later in Roe v. Wade.

At the time, though, the most striking response to Olmstead came from the Anti-Saloon League. Extracting the gist of comments made by S. E. Nicholson, the ASL’s New York superintendent, the Times summarized the league position: “It is feared by the dry forces that Prohibition will fall into ‘disrepute’ and suffer ‘irreparable harm’ if the American public concludes that ‘universal snooping’ is favored for enforcing the Eighteenth Amendment.” Said Nicholson, “We do not favor the decision unless it is to be interpreted as applying to all criminal cases of every kind.” It was an impossible position. On the one hand, the league was acknowledging the unpopularity of this particular expansion of federal authority. But, in an attempt to dodge responsibility for Olmsteadand the other unpopular snips and slices that were increasingly perforating the Bill of Rights, the league wanted to suggest that these alterations were meant to address crime in general and were not specifically about Prohibition at all.

The ASL leaders were wise to be worried. The only thing that seemed to be multiplying faster than federal power was criminal violence. No sooner had the flow of liquor from Rum Row in the Northeast been stanched than it began to gush in unprecedented quantities through the sluiceway that was Detroit, where an overmatched prosecutor said, “The greatest obstacle to the attainment of Prohibition is the Constitution of the United States, the instrument that decreed its birth.” Corruption and incompetence had metastasized throughout the Prohibition bureau to such a degree that Wayne Wheeler had been forced to capitulate and allow bureau agents to be placed under the protection of the Civil Service, even at the cost of ceding the ASL’s rich garden of patronage. On the Supreme Court, William Howard Taft, who had once feared the destructive power of Prohibition but had since become its most influential defender, sensed the looming breakup of his coalition as Justices Holmes, Brandeis, and Stone increasingly abandoned pro-enforcement positions.

The tightrope that Wheeler and the ASL walked—the one suspended between its hunger for stiff enforcement and its wish not to offend public sensibilities with federal overreaching—had first threatened to snap in early 1927. Several New Yorkers died and hundreds had been rendered gravely ill during the 1926 holiday season; all had consumed industrial products that had been denatured with poisonous wood alcohol. Wheeler’s response was chilling. “The government is under no obligation to furnish the people with alcohol that is drinkable, when the Constitution prohibits it,” he told the press. “The person who drinks this alcohol is a deliberate suicide.”

Reaction was swift, and enraged. Senator Edward I. Edwards of New Jersey said Wheeler was condoning “legalized murder.” Andrew Mellon declared his opposition to the use of toxic denaturants, a practice he considered “inexcusable.” Morris Sheppard, trying to bail Wheeler out, argued that overindulgence in alcohol was the real killer. But wets who’d endured years of lectures about the dangers of alcohol easily punctured this argument. “If the Senator’s theory is that alcohol is so poisonous,” asked wet Senator Edwin S. Broussard of Louisiana, “then why put poison in it?”

Such was the prelude to Wheeler’s appearance on the stage of Carnegie Hall three months later, his most widely noticed public appearance since the disastrous Reed hearings. Now he was stepping into the den of a lion who was every bit Jim Reed’s equal. Wheeler had agreed to debate Clarence Darrow in front of a sure-to-be-hostile New York audience, despite his own increasingly ill health and Darrow’s certain invocation of the still-simmering poison controversy. Darrow did not disappoint, ripping into Wheeler and other drys who, he said, believed that “any man who takes a drink of alcohol today may be poisoned without a trial by a jury, without anything, just be poisoned because he dared take it!” For this one time Darrow was on the prosecution’s side, and the prisoner in the dock was Prohibition itself. Vigorous and theatrical, alternating between corrosive sarcasm and heaven-shaking grandiloquence, the seventy-year-old Darrow deployed all his courtroom skills. It was as if he were addressing a jury, but in this case a jury composed of twenty-five hundred New Yorkers, the overwhelming majority of whom had come to Carnegie intent on delivering a conviction. So intent, in fact, that those in the first-tier seats had paid $11 apiece—the 2009 equivalent of $135—for the privilege.

Wheeler’s arguments were sharper than Darrow’s, and his command of the facts he had invoked so many times over the preceding quarter century was firmer. But he didn’t stand a chance. He was steamrollered by his opponent’s rhetorical power, overwhelmed by the audience’s hunger for blood, and disabled by his physical condition. Wearing his finest uniform—full evening dress, complete with white tie—Wheeler nonetheless looked pale, withered, somehow empty. He didn’t even present his opening remarks himself; instead, his colleague Scott McBride read from a prepared text while the audience booed and hissed and jeered. Even the ferociously anti-Wheeler New York World expressed sympathy. He was, the paper said, “engaged in a one-handed fight against 2,000 booing, hooting, caterwauling New Yorkers, who tried all at once to tell him where to get off.”

But, the paper continued, “the small, spunky, bespectacled, baldish man in the clawhammer coat didn’t get off at all.” Freeing McBride from his ventriloquist duties during the rebuttal, speaking in a voice that could barely be heard beyond the first few rows, Wheeler presented a logical, acute, and shapely response that took into account every familiar argument for Prohibition and a few others besides (“Did you ever hear of a man eating so much pie or cake or anything of that kind that he’d go home and shoot up the family?”).

Near the end of his talk Wheeler landed, like Chief Justice Taft, in Prohibition’s best-defended fortress: the rule of law, as established by the will of the people. He declared that the people had placed the Eighteenth Amendment in the Constitution, and only the people could remove it, and everyone in the hall knew that to accomplish that, anti-Prohibition forces would have to muster the support of two-thirds of a dry Congress and three-quarters of a collection of states that were very dissimilar to New York. This was something the night’s only other speaker, Mayor Jimmy Walker, had acknowledged. Arriving midway through the event, Walker addressed the audience in his characteristically jovial fashion. To this crowd of knowing New Yorkers, most of whom might have come to Carnegie Hall either on the way to or from a speakeasy, the mayor proclaimed that although he was a confirmed wet, “Prohibition might be a good thing—but I don’t know who is going to arrange it.”

Yet even Walker knew when it was time to stop with the wisecracks and address the real issue. “Those of us who don’t like Prohibition,” he concluded, “ought to stop complaining and organize and get rid of it, or shut up.”

* The Dwyer trial involved sixty defendants, including thirteen Coast Guardsmen and a rising young hood named Francesco Castiglia, who were charged with a conspiracy that reached as far as the Gulf and the Pacific Coast, and was alleged to have been responsible for millions of dollars in smuggled liquor, official corruption on a grand scale, and twelve deaths. Dwyer served barely a year in prison; Castiglia, who would soon become known as Frank Costello, was the beneficiary of a hung jury.

* The very few dry papers in major cities included the Des Moines Register, the Los Angeles Times, and the Brooklyn Eagle. Another, the Detroit Free Press, started off dry but in 1925, wishing to “save the youth of the nation from its present position,” declared its earlier stance “a fearful error.”

* McReynolds, who had been appointed by Woodrow Wilson, hated Prohibition—but hatred was his defining characteristic. Unembarrassed by his virulent anti-Semitism, he not only refused to speak to Justice Brandeis (and, later, Justice Benjamin Cardozo), but he turned his back to them when they spoke during oral arguments. He displayed his consuming misogyny by doing the same to Mabel Willebrandt and other female attorneys who appeared before the Court.

* This case, United States v. Manly S. Sullivan, became the foundation of the government’s eventual conviction of Al Capone for income tax evasion. It also provoked from Justice Holmes a bemused consideration of the defendant’s argument that requiring the filing of a return for illegal income would logically entitle the filer to deduct illegal expenses, such as bribery. Wrote Holmes, “This by no means follows, but it will be time to consider the question when a taxpayer has the temerity to raise it.”

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