A true child of the jazz age, Thompson had been born in Boston in 1867 to a family of considerable means. Detesting school and the confines of the East, he went west in search of adventure and worked as a brakeman for the Union Pacific Railroad, a ranch hand, and a self-styled cowboy. He gravitated toward Chicago to indulge his taste for lavish living and subsequently entered politics, it was said, on a fifty-dollar bet. Scandal pursued him wherever he went. During one campaign, he was forced to admit he had frequented Chicago brothels. Sexual hypocrisy came naturally to him; he married a proper dowager, who lent him an aura of Victorian respectability even as he kept an attractive Jewish mistress. He ate and drank with abandon. Flamboyance was his trademark. During the Dever administration, for instance, Thompson built himself a $25,000 yacht, christened her Big Bill, arranged for a figurehead depicting none other than the ship’s owner, and, to the vast amusement of the press, declared his intention to lead an expedition to capture a certain fish reputed to climb trees. He traveled down the Mississippi River on the Big Bill, pausing at towns along the way to make political speeches and to do whatever he could to attract attention to himself.
He never did find his tree-climbing fish, but he did manage to start a Thompson-for-mayor boom, which he cultivated carefully on his return to Chicago. There the race already included two of his protégés, Fred Lundin and Dr. John Dill Robertson, who had served as the city’s health commissioner. Thompson viewed their entry into the mayoral race as treachery, and he was greatly annoyed. To exhibit his displeasure, he rented the Cort Theatre, where he staged a political vaudeville in the form of a Rat Show, in which he appeared on stage bearing a cage holding two rats. One, he told the audience, was called Fred and the other Doc, after his rivals. “Fred,” he addressed one of the rats, “wasn’t I one of the best friends you ever had?” And to the other rat, he said, “I can tell this is Doc because he hadn’t had a bath in twenty years until we washed him yesterday.” (This was a reference to Robertson’s position as health commissioner.) Thompson ended his demonstration by explaining that the cage had formerly held six rats, but Doc and Fred had devoured the others. The audience loved the show, and Thompson suddenly became a viable candidate for mayor. His opponent was, once again, William E. Dever, whom Thompson began denouncing as that “left-handed Irishman.” Wherever he went, he whipped up anti-Catholic prejudice against Dever. The articulate, decent Dever was by no means an easy target, for he enjoyed immense prestige, though much of it came from outside Chicago. In fact, he was widely regarded as the nation’s ablest mayor, the man Chicago required to defeat its gangsters. As the campaign wore on, Dever took the high road, and a dull journey that proved to be, while Thompson took the low, and far more entertaining, route to power.
As the race narrowed in the early months of 1927, Thompson deftly shifted from vaudeville stunts to outlandish demagoguery. Once again he lambasted the tyrannical King George and attained new heights of absurdity when he criticized the number of pro-British books in Chicago’s libraries; “treason-tainted histories,” he labeled them. To rid themselves of this menace, he urged the citizens of that fair city to pillage the treacherous libraries and burn the offending books. Thus did Thompson distract the populace and inflame their imaginations with spurious campaign issues of his own devising.
Attempting to parry Thompson’s fatuous remarks, Mayor Dever threw up his hands in frustration. “How can I campaign against a brain like that?” he complained. Even he had to admit that his commonsense, literal-minded campaign paled before the fanciful guile Thompson spouted, especially on the subject of Prohibition. Ever the harlot of the voting booth, Thompson insisted that he was “wetter than the middle of the Atlantic Ocean,” and to prove his point, he vowed to allow every speakeasy Dever had shut down to open once again and to add 10,000 new speakeasies to the already-sodden Chicago landscape. To lend credibility to this promise, the Thompson campaign headquarters served some of the best bootleg booze to be had in the entire city.
Chicago’s reputation as a crime-ridden haven for gangsters inevitably became an important issue in the campaign, perhaps the only real issue. Although Dever could lay claim to honesty, if not effectiveness, in this regard, Thompson quickly seized the initiative by blaming the city’s criminal atmosphere on his opponent. He took out a large ad in the Chicago Tribune in which he warned, “The city is overrun with morons and other vicious elements. The papers teem with accounts of murders and other horrible lawlessness. Thompson pledges himself to change these conditions and make life and property once again secure in Chicago.” “Big Bill” saw nothing inconsistent about condemning gangsters even as he sought backing from Capone and other racketeers. The only thing that mattered to him was getting the vote, even if it meant creating a carnival of hysteria.
For all his anticrime propaganda, it would be difficult to imagine a politician better suited to further the aims of Chicago’s racketeers than Thompson, but Capone, becalmed in a premature retirement, resisted Thompson’s sweaty overtures. They were both Republicans, it was true, but even though Thompson was infinitely corruptible, Capone considered him a fool, untrustworthy and unreliable. The racketeer preferred the public servants he controlled to be low-profile, no-nonsense types, like his man in Cicero, Edward Z. Klenha. Capone valued discretion, the appearance of honesty, but Thompson was a walking scandal, altogether too messy, provocative, and colorful. When Thompson courted the favor and financial backing of racketeers, he received an outpouring of cash from saloon owners, who were understandably delighted with his determination to ignore Prohibition, and he attracted the support of “Schemer” Drucci and Jack Zuta, who oversaw vice and gambling operations for “Bugs” Moran and came forward with a $50,000 contribution.
Not to be outdone by his dimwitted but dangerous rivals, Capone secretly contributed $260,000 to the Thompson campaign, more in self-defense than from a genuine desire to see the man elected. This was strictly a cash transaction, casually dispensed during the campaign. According to the Chicago Crime Commission’s investigation of the election, the “money was ladled out to Thompson workers from a bathtub in the Hotel Sherman, filled with packages of $5 bills.” The money naturally came with various strings attached. The first concerned territory: “Capone should have the undisputed right to houses of prostitution and gambling houses, to operate slot machines, and control the sale of beer and booze in all the territory of the city south of Madison street,” the Chicago Tribune revealed. The second quid pro quo involved people. The Thompson Republican Club soon numbered various Capone cronies such as Morris and Emmanuel Eller, a father-and-son team who paid men to vote twice, and Daniel Serritella, who represented the Unione Sicilione. All of them received influential appointments under Thompson. When news of the Capone contribution eventually leaked out, Thompson’s political rivals and the press outdid one another to denounce the arrangement.
As the April election approached, the Chicago police braced for an outbreak of gangland violence. Election eve found the deputy chief of police, John Stege, carefully instructing his men on the use of the tommy gun. Two hundred fifty “flivver squads” patrolled the length and breadth of the city on election day, but police encountered little of the wanton slugging and kidnapping associated with past elections. It was true that one or two election judges were kidnapped and beaten within an inch of their lives, and five shots were fired, and a couple of Democratic clubs were bombed, but considering this was a Chicago election, these incidents barely registered. Voters joked nervously whenever a passing automobile backfired; no, they reminded themselves, it was not a shotgun blast.
Everyone from the police to the Dever supporters expected Capone to send his troops into battle, but unenthusiastic about Thompson and determined to preserve his “retired” status, Capone and his men were nowhere in evidence. “Schemer” Drucci, however, could not resist throwing himself into the fray. To help out his man, “Big Bill,” Drucci decided to kidnap a Dever supporter, Alderman Dorsey Crowe, on election day, Apri
l 4, and hold him overnight. But Drucci wasted precious time destroying the office and pummeling Crowe’s secretary and never did accomplish his goal. He and two colleagues were caught on the corner of Diversey Parkway and Clark Street the same day. The police relieved Drucci of his .45 and held him in custody. Eventually his lawyer, Maurice Green, came forward to demand his client’s release, and four policemen were assigned to escort Drucci to the Criminal Courts Building, where Green waited. The police detail included Danny Healy, a tough cop who had once dared to beat up “Polack Joe” Saltis, the bootlegger. As the police car sped through the streets of Chicago, Healy taunted Drucci until the gangster was in a rage, restrained only by the gun the cop aimed at his heart. Healy later gave this account of the ensuing struggle: “Drucci said, ‘You—I’ll get you. I’ll wait on your doorstep for you.’ I told him to shut his mouth. Drucci said, ‘Go on, you kid copper—I’ll fix you for this.’ I told him to keep quiet. Drucci said, ‘You take your gun off me or I’ll kick hell out of you.’ He got up on one leg and struck me on the right side of the head with his left hand, saying, ‘I’ll take you and your tool. I’ll fix you,’ grabbing hold of me by the right hand. I grabbed my gun with my left hand and fired four shots at him.’ ” Drucci collapsed, and by the time the car arrived at the Criminal Courts Building, he had died.
Drucci’s lawyer cried for Healy to be arrested for murder, but on hearing the demand, William Schoemaker, the chief of detectives, replied, “I don’t know anything about anyone being murdered. I know Drucci was killed trying to take a gun away from an officer. We’re having a medal made for Healy.” The police could barely conceal their amazement that “Schemer” Drucci was dead and that one of their number had killed him. A cop actually killing a gangster—not taking his money, not drinking his bootleg booze, not looking the other way—this was a rare event in Chicago. In fact, Drucci was the first racketeer of significance to die at the hands of the police since the shooting of Frank Capone three years earlier. Another day in Chicago brought another gangster funeral, this one with a military flourish (“Schemer” Drucci was a veteran), another silver casket at Sbarbaro’s Funeral Home, and another burial at Mt. Carmel Cemetery, fast becoming the Arlington National Cemetery of Chicago’s gangland wars. His widow, who stood to inherit his $400,000 estate, was not especially grief-stricken. Cecilia Drucci—the picture of a flapper—sighed sweetly and said to a reporter, “A policeman murdered him, but we sure gave him a grand funeral.”
If Cecilia Drucci was strangely heartened and the chief of detectives delighted by Drucci’s death, Capone’s pleasure at hearing the news can only be imagined. At a stroke, Drucci was gone. Weiss was gone. Everything was breaking Capone’s way. Of his worst enemies, only “Bugs” Moran was left, along with his ragged crew of bootleggers and gunmen, and they were no match for Capone’s well-heeled, experienced organization. But anyone with a machine gun and sufficient nerve was dangerous, and Capone maintained a healthy fear of Moran and a mounting conviction that something would have to be done about him at the right time and place.
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To no one’s surprise, William Hale Thompson carried the election, receiving 515,716 votes to Dever’s 432,678. That night the Thompson forces held their victory celebration in the opulent Louis XIV Ballroom at the Sherman House, where they shouted their hero’s campaign anthem until they were hoarse, and “Big Bill” himself cavorted in a ten-gallon hat. Later that night he invited his supporters to toast the victory aboard his yacht, the Big Bill. The crowd accepted his offer in such numbers that his ship of fools sank to the bottom under their weight. Thompson scrambled to safety, as wet, cold, and boisterous as ever. Vowing to discharge the responsibilities of his office with the same gusto he had brought to his campaign, he took the oath of office on April 13, 1927. Shortly afterward he established the custom of driving around the streets of Chicago at night in an open touring car with a spotlight trained on him. “The people like to see their mayor,” he explained. And so they did.
Now that Thompson was back in office, Capone realized that his contribution had been the best quarter of a million dollars he had ever spent. Without lifting a finger or exposing himself to criticism, he had gotten rid of the detested Drucci, and Thompson, bigoted oaf though he was, removed all local obstacles to the smooth operation of Capone’s organization. Indeed, one of the mayor’s favorite nightspots was Ralph Capone’s Cotton Club in Cicero, which became the common ground of racketeers and politicians alike. With the return of “Big Bill” to City Hall, Chicago politics underwent a rapid transformation; Dever’s impotent fury at gangsters and Prohibition violators yielded to Thompson’s easy indulgence and pandering. He took care to pay off his backers; Capone’s ally, Dan Serritella, received an appointment as city sealer, and as the inspector of weights and measures he was ideally positioned to receive an endless supply of bribes. (Several years later, he was convicted of defrauding the city.) He also became Republican committeeman in the First Ward and as such Capone’s principal link to City Hall.
Buoyed by his success, Thompson developed ambitions extending far beyond Chicago. He interpreted his victory as a mandate to launch a national campaign. When President Coolidge declared he would not run for reelection in 1928, Thompson promoted himself—and, even more remarkably, people began to consider him—as the next Republican candidate for president. If Warren G. Harding could make it to the White House, why not William Hale Thompson?
To whip up enthusiasm for his presidential candidacy, “Big Bill” invited his friends and a Police Department quartet to accompany him in a private railway car, and the troupe set off on a ten-thousand-mile cross-country speaking tour, stopping at state fairs and prairie towns to denounce such infamies as the League of Nations and the World Court, anything that threatened, in Thompson’s view, the idea of “America First.” Thompson was greeted with affection and respect throughout the Midwest, as far west as San Francisco, and as far south as New Orleans, where the Kingfish himself, Huey Long, soon to become the governor of Louisiana, held a banquet in Thompson’s honor. At a loss for conventional words to describe the boom, the New York Times coined the term “Bigbillism.”
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In May 1927, the U.S. Supreme Court handed down a ruling that was but a whisper amid the din of “Big Bill”’s Chicago, although eventually it would have profound consequences for that beleaguered city, “DECIDES BOOTLEGGERS MUST MAKE TAX RETURN,” the headline in the New York Times neatly summarized. “Supreme Court Holds They Are Not Immune Because of Violating Dry Law.” The decision had come about as a result of a case that arose in Charleston, South Carolina, where lawyers argued that the Fifth Amendment to the Constitution forbidding self-incrimination protected their client, a bootlegger named Manley Sullivan, from the necessity of filing a tax return and paying taxes on his ill-gotten gains. In response the Court amended the law in a small but significant way by ruling that from now on income derived from illegal sources of revenue must also be reported and was subject to income tax. The author of the opinion, Associate Justice Oliver Wendell Holmes, wrote, “We are of the opinion that the protection of the Fifth Amendment was stretched too far,” and he proceeded to explain, “It would be an extreme if not extravagant application of the Fifth Amendment to say it authorized a man to refuse to state the amount of his income because it had been made in crime.” In other words, income was income, whether legitimate or not. The ruling was aimed at two large shadow industries that had grown mightily during Prohibition; one was gambling, such as betting on horses, and the other was bootlegging. What the ruling said, in effect, was that bootleggers such as Al Capone must pay taxes on their entire incomes.
The Supreme Court ruling caused a brief flurry. The Times commended the decision and emphasized its application to bootleggers who “make fabulous profits, but . . . must pay their taxes just the same as less favored mortals.” At first, the ruling did little to change the status quo, and bootleggers did not start inundating the IRS with their r
eturns. However, the Internal Revenue Service took the ruling as a legal basis to demand that gamblers and bootleggers pay taxes on their ill-gotten gains, and they were prepared to prosecute to achieve this goal. The racketeers scoffed; none of them was foolish enough to pay taxes on their illegal gains. They might just as well walk into the office of the U.S. attorney general and surrender. Like every other racketeer, Al Capone would no more dream of filing an income tax return than he would allow an honest race to be run at the Hawthorne Race Track.
At first glance, the ability of the IRS to catch Capone or any other bootlegger of consequence appeared extremely limited. Ever since Congress first began imposing a federal tax on income in 1913, the IRS had faced the problem of compliance, especially when it came to tax dodgers such as Capone. Under the stewardship of a former Post Office stenographer named Elmer Irey, the agency set up a Special Intelligence Unit designed to catch these offenders; despite its exalted title, which often struck other government bureaucrats as more than a little pompous, the unit toiled in the shadow of the Federal Bureau of Investigation; few people were aware of the unit’s existence and even fewer cared. Furthermore, Irey’s enemies constantly deprecated him and spread groundless tales of drunken behavior. Now, at a stroke, the Supreme Court decision gave the IRS and its Special Intelligence Unit real power. Irey, a prickly, self-effacing civil servant, rolled up his sleeves and began to investigate the most visible racketeer in the country’s most corrupt city: Al Capone.
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