THE STREETS AROUND Arcadia Hall began to fill sometime after dusk on January 14. As evening fell, swarms of people began streaming from the North Side streetcars, joining pedestrians already on their way toward the large barrel-roofed structure at Broadway and Sunnyside in Uptown. By seven, large crowds—including many women, legal voters in Illinois municipal elections since 1913—had formed around the main entrance, spilling out into traffic on the street.

Once the doors opened, the cavernous auditorium quickly filled to capacity. Spectators crammed themselves into every available space, including the gallery at the back of the hall and the area behind the broad elevated stage. While some of these people were clearly Republican Party hacks and members of the campaign’s “portable audience” (hired to fill out rooms around the city), many others had come of their own accord, simply to witness what they knew would be the best free entertainment in the city: Tonight, the mayor of Chicago would announce his candidacy for a second term.¹

At eight o’clock, Samuel Hamilton, vice president of the Twenty-fifth Ward William Hale Thompson Club, called the assembly to order. He introduced the Chicago Marine Band, which warmed up the audience with a varied program of music, including a sing-along of the anthem “America,” two violin solos by a young soldier named W. A. Dalpé, and “The Cycle of Life,” a soprano solo sung by Mrs. Milton Severinghaus, wife of the program’s musical director. Finally, the audience joined the singers on stage in a rousing performance of “The Man of the Hour,” the latest Thompson campaign song, reading the newly minted lyrics from a signboard hoisted above the stage for all to see:

Over here we have a leader

Who’s been fighting for you and me.

Ever since he’s been elected

He’s been square as man could be.

Though lying newspapers may lie,

You hear the honest voters cry:

We’ll elect Big Bill for our next mayor!

To warm applause, the members of the mayor’s cabinet and other dignitaries filed onto the stage. The evening’s emcee—Irene Pease Montoya, daughter of Republican warhorse James Pease—rose to give the introductory address, praising the man who had given Chicago “the best administration in its history.” She then introduced City Health Commissioner John Dill Robertson, who whipped the crowd to further heights of enthusiasm until, with a shout, the guest of honor appeared in the hall to interrupt Robertson’s accolades. Waving his trademark ten-gallon cowboy hat to acknowledge the riotous reception, he pushed his way through the cheering throngs, mounted the platform, and strode to the center of the stage. And there he stood for several minutes, jubilantly drinking in the applause and cheers he loved above all else: the man of the hour himself, Big Bill Thompson.²

No one could deny that the mayor of Chicago knew how to command a stage. A six-foot-plus bear of a man, his 225 pounds straining the seams of an indifferently tailored suit, he was not one to blend into a crowd. Decades of banquets and gravity had taken their toll on the former athlete’s physique, but he was, at fifty-one, an impressive figure nonetheless, with a thick bull neck and a barrel-shaped chest that still seemed sturdy enough to stop a rushing fullback in his tracks. Rumor had it that a younger Big Bill had once knocked out three men in a bar fight in Wyoming. Those days were perhaps gone, but although he now sported a paunch (known as an “alderman” in the parlance of the day) as well as an extra chin or two, he still looked like the man you’d want to stand beside—or behind—when the bar stools and whiskey bottles started flying.

But the nickname “Big Bill” referred to more than just the mayor’s physical proportions. There was something about the expansiveness of his personality, too, that made the title apt—his boyish enthusiasm, his flamboyant sense of showmanship, his sloppy and uncritical optimism, his Rabelaisian appetite for life. Thompson was naturally gregarious, so much so that even his enemies—of which there were many—admitted that they found him disconcertingly likable once they actually sat down with him. And the mayor’s affection for Chicago, the city he grew up with, was nothing if not genuine and infectious. William Hale Thompson, as one of those enemies later wrote, “loved Chicago like a boy loves his dog—heavily and sentimentally.”³

And, to a large extent, Chicago loved him back. Not, admittedly, the Chicago of prim-faced college professors, teetotaling clergymen, and settlement house do-gooders; but the rank and file of the city—the button makers and the livery drivers, the hotel porters and the packinghouse butchers, the small shopkeepers, the grocery clerks, and the tavern owners. These Chicagoans recognized Big Bill as one of their own. He spoke their language—“slangy, vulgar, and alive”—and seemed to understand their concerns better than an institute full of good-government reformers. Granted, maybe he wasn’t entirely honest, but what politician was? Besides, he got things done. Under Big Bill’s administration, unemployed sons and brothers-in-law were given jobs; viaducts and playgrounds were built; money was spread around. The best administration in the city’s history? On this day, in this auditorium, and among this crowd, who would dare to deny it?

When the ballyhoo at his appearance finally abated, Big Bill stepped forward and thanked the audience for its generous and hearty welcome. “I have been requested by petition from more than 200,000 men and women voters of Chicago to become a candidate for reelection to the office of mayor,” he announced. And then, with perfect dramatic timing, he added, in his familiar “big, boozy, bellowing” roar: “I take this opportunity to announce that I will comply!”

The hall erupted yet again with boisterous applause and cheering. Not that anyone in the audience had been in doubt about his intentions, but now it was official: Big Bill wasn’t going to let them down. One of the most remarkable and controversial political figures in American history was about to pick up the cudgels and fight for a second term.⁴

*   *   *

He was not the likeliest of mayors, even in a city notorious for unlikely chief executives. Given the trajectory of his early life, it was remarkable that he had even entered politics in the first place. Born in 1867 to a wealthy Brahmin family on Beacon Street in Boston, he was brought to Chicago when he was still an infant.⁵ His father, William Hale Thompson Sr., was a prominent businessman who had graduated from Yale, served with Admiral David G. Farragut at Mobile Bay during the Civil War, and then established himself as a successful Chicago real estate developer. Bill Jr. was groomed to follow in these footsteps. Related on his mother’s side to one of Chicago’s original founding families and on his father’s side to an intimate of George Washington, he seemed destined to become a pillar of Chicago’s educated and moneyed elite. Except, that is, for one small peculiarity: Young Bill really wanted to be a cowboy. Never one for study and discipline, he instead harbored dreams of busting broncos under a spacious Western sky. And so, at the age of fourteen, he had made a deal with his parents. After an embarrassing incident in which he was briefly jailed for riding his horse recklessly across the State Street Bridge (allegedly toward a make-believe Indian battle in Lincoln Park), he promised to make amends. He would buckle down and get a job in a grocery, he said—if his parents would allow him to use his earnings to pay for an extended adventure out West. They agreed to these terms, perhaps suspecting that the boy would lack the discipline to save money. It would not be the last time someone underestimated Billy Thompson’s resolve. The following autumn, the boy was happily riding in the caboose of an empty cattle train, heading west.⁶

The Great Plains, as it turned out, suited Thompson perfectly. For the next six years, he spent the warmer months on the prairie (as a brakeman for the Union Pacific Railroad and a wagon driver at a Wyoming cattle ranch) and his winters back in Chicago (at the Metropolitan Business College, where he was known to appear occasionally in full cowboy garb). By 1888—convinced finally that their son really wasn’t cut out for a career spent uneventfully multiplying the family fortune—the Thompsons purchased a ranch in Ewing, Nebraska, and asked Bill to run it. He was delighted to obey.

For three more years, he lived the life of the Western rancher, this time on a year-round basis. He led packs of his cowboy compadres on wild horseback rides down Ewing’s Main Street. He hosted visits by city-slicker friends from Chicago (among them a young Flo Ziegfeld, well before his theater-producing days) and staged mock gunfights for them. High jinks aside, he also saw to the business of buying, feeding, and selling cattle at profit. Again exceeding low expectations, he turned the ranch into a highly lucrative business venture, clearing a profit of $30,000 (roughly $700,000 in current dollars) over the course of three years.

This western idyll, however, could not last forever. When William Hale Sr. died suddenly in 1891 (leaving an ample estate of more than $2 million), the twenty-four-year-old cowboy was forced to return to Chicago to take over the family real estate business. But even then, politics was the furthest thing from Big Bill’s mind. Instead, he threw himself into the nearest urban equivalent of cowpunching—amateur sports. At the prompting of his childhood friend Eugene Pike (another young millionaire with time on his hands), he joined the Chicago Athletic Club. Within a year, he was captain of the club’s water polo team, competing successfully against teams from Princeton, Harvard, and Yale. In the national finals against the New York Athletic Club, Bill reacted to some aggressive play by unceremoniously walloping his opponent in the nose. His team ultimately lost the match, but Thompson himself won the adoration of Chicago’s sports fans, who took to calling him “Fighting Bill.”

From there, he moved on to other sporting triumphs—in baseball, football, diving, handball, even the aerial trapeze.⁷ By the late 1890s, he had become a well-known figure around Chicago—not only on its playing fields, but also (to the chagrin of his mother) in the taverns and brothels of the Levee, the city’s notorious South Side entertainment district. Then, one day in 1899, during a card game with friends at the club, Gene Pike tried to convince him to go into politics. Pike himself had just won election as one of the Second Ward’s two aldermen. Now he wanted Big Bill to run for the ward’s other council seat. But Thompson was unsure he wanted to jump in.

George Jenney, another club member, scoffed at Thompson’s hesitation, claiming that Big Bill was afraid to run. Jenney took a fifty-dollar bill from his wallet and put it down on the card table. “This money says Bill Thompson is scared!”

It was a challenge no true sportsman could leave unmet. Acting before Pike could answer, Thompson put his hand out and covered the bill. “I’ll take this one myself,” he said. “George Jenney, you’ve got yourself a bet!”⁸

*   *   *

Once the Arcadia Hall crowd settled down after his opening announcement, the mayor wasted no time before launching into his campaign pitch. It was a speech that, in one form or another, he would deliver in countless venues before countless audiences over the next few months. As usual, he began on a positive note, his manner calm and confident, his diction almost formal. The fireworks would come later.

“An examination of the past four years,” he declaimed, “will prove that I have given Chicago an honest, economical business administration, abounding with constructive achievements!”⁹

Holding up an index finger in one of his trademark gestures, he proceeded to enumerate these achievements—a reduction in crime citywide; the divorcing of the police from politics; preservation of the five-cent transit fare; and, of course, his ongoing building projects. He boasted shamelessly about the widening and improvement of city streets, the gargantuan Michigan Avenue development, and all of the other Chicago Plan endeavors that he had been working so hard to bring to fruition. All of this, he claimed, amounted to a mighty record of accomplishment, and yet it had been achieved without undue strain on Chicago taxpayers. The city’s government, in fact, had been run “with less revenue … and with greater efficiency in every department than ever before!”

Arcadia Hall erupted once again with applause and shouts. Yes, this was the capable, can-do mayor Chicago had elected four years ago. Never mind the venal and incompetent Mayor Thompson depicted by the “lying newspapers.” This was “the People’s David,” who fought for the common man’s interests in the name of the common man. This was Big Bill the Builder!

“I know that a vast majority of the people desire good government,” the mayor went on, shifting to a quieter tone, “[and that] the most important element in securing good government is an intelligent vote of the people. If people are to vote intelligently, they must know the truth about their public servants and public affairs. [But] how are the people to know the truth? What are their sources of information?”

He let the question hang in that great space for a moment. The audience, he knew, was in his hands now. And they, in turn, knew exactly what was coming next. It was, in fact, the reason many of them had attended the meeting in the first place. The mayor was getting ready to start the real show of the evening. He was about to go on the attack against his enemies. The fireworks were about to begin.¹⁰

*   *   *

He had taken to politics immediately. Elections, after all, were not so different from the sporting matches he loved—you played hard, you worked your advantages, and at the end of the game there was a winner and a loser. Big Bill liked being a winner, and so he had thrown himself wholeheartedly into that first campaign. The Second Ward in 1900 was a diverse area, embracing part of the red-light district as well as the Prairie Avenue silk-stocking neighborhood, but Thompson proved adept at appealing to both constituencies. Nominated at Freiberg’s Hall, one of the Levee’s most notorious dens of vice, he nonetheless ran on a reform platform, promising to clean up the streets and battle crime, which pleased the well-heeled progressive set. He also proved to be an indefatigable and openhanded campaigner, buying drinks for prospective supporters at every one of the ward’s 270 saloons. “I’m spending $175 a day,” he remarked to friends during the campaign. “I’ve worn out two pairs of shoes and I’ve gained 14 pounds. Fellows, politics is really the life!”

The strenuous glad-handing paid off. Thompson won the election by a comfortable margin and joined his friend Gene Pike on the city council. He proceeded to get married (to Maysie Wyse, a pretty secretary from his real estate office) and tried to interest himself in the day-to-day operations of city government. But Big Bill soon found that actually serving as alderman was somewhat less enjoyable than campaigning for the job. He proved to be an indifferent councilman, rarely attending sessions and racking up few legislative accomplishments. Tricked by his savvier colleagues in the First Ward (the legendarily corrupt Michael “Hinky Dink” Kenna and “Bathhouse John” Coughlin), he even naively voted for a redistricting ordinance that changed the boundaries of the Second Ward, essentially moving his own residence out of the ward and making it impossible for him to seek reelection. The erstwhile cowboy, it seemed, had shot himself in the foot with his own six-shooter.¹¹

It was obvious that if Thompson wanted to go any further in politics, he would need a mentor. And he soon found one in the person of William Lorimer. Known as “the Blond Boss” of Illinois politics, Lorimer was head of the city’s West Side Republican organization, and he saw in Thompson the raw material of a political comer. Lorimer discouraged Big Bill from trying to get revenge on Bathhouse John by running against him in the First Ward. “No one’s going to beat Bathhouse,” Lorimer told the young alderman. “You turn your ward delegates over to me and I’ll put you up for county commissioner. That way you can run where there are some Republican votes. Tie to me, Bill.”

Never one to balk at a blatant quid pro quo, Thompson gladly accepted the offer. Associating himself with the powerful Lorimer machine, he ran for county commissioner in 1902 and won. This was gratifying, especially since the position didn’t require all that much work. But again Thompson ended up serving just a single undistinguished term. Losing his bid for reelection in 1904, he decided to quit public office and return to his sporting activities, reinventing himself this time as a successful yachtsman. Even so, he remained active in politics as a party committeeman, working tirelessly in the Lorimer cause as the Blond Boss managed to win himself a seat in the U.S. Senate. Meanwhile, Thompson cultivated other political connections, particularly with fellow wealthy pols George F. Harding and James Pugh (who had helped Big Bill during the 1902 campaign by sitting in the front row at Thompson’s stump speeches and dropping a brick whenever the candidate forgot to smile).¹²

The most important connection Thompson made during these years, however, was with Fred Lundin, a one-term congressman who had quickly risen to become a major figure in the Lorimer organization. Widely known as “the Poor Swede” (evocative nicknames were something of an obsession in Chicago politics), Lundin was a true eccentric—a diminutive, bucktoothed “square head” who wore enormous eyeglasses and an old-fashioned black frock coat with flowing bow tie. Affecting the modest persona of an immigrant yokel with just an average citizen’s interest in politics, he was actually a fiercely ambitious and ruthlessly manipulative operator, a former patent medicine salesman who had parlayed a one-wagon peddling enterprise into a substantial business empire. As such, he knew the value of hoopla and razzle-dazzle, especially when selling something, even a political candidate, to the public. “Get a tent,” he was wont to tell his protégés in a lilting Swedish accent. “Give them a show, forget about the issues. Give them a good time and you get the votes.”

In Thompson—a crowd-pleasing showman who loved the bare-fisted combat of campaigning—the Poor Swede recognized the perfect receptacle for this political wisdom. The fact that Big Bill wasn’t overburdened with scruples or philosophical convictions only increased his appeal. “He may not be too much on brains,” Lundin allegedly once said of him, “but he gets through to people.” And so Lundin became Big Bill’s new mentor and proceeded to lay the groundwork for his political future.¹³

Even so, it took over ten years and the demise of William Lorimer to put Thompson and Lundin in a position to make their move. In 1912, Lorimer, accused of bribing several Illinois state representatives to win election, was expelled from his Senate seat. For the Blond Boss, of course, this was a career-breaking disaster. For the Poor Swede it was a golden opportunity, a chance to pick up the pieces of a shattered political organization and rebuild it in his own image. And so, from the routed elements of the West Side Republican machine, he gathered together a core group that would come to be known as “the Five Friends,” including Lundin himself, Thompson, George Harding, the brick-dropping James Pugh, and Thompson’s old friend Gene Pike. Together they planned what one historian called “a thrust for power never before attempted by any little political group.” Their goal, as far-fetched as it may have sounded at the time, was to elect from their number a mayor, a governor, and, finally, if they were lucky enough, a president of the United States.¹⁴

There was, of course, no shortage of people in Chicago determined to stand in their way.

*   *   *

He began, as usual, with the newspaper editors. As the Arcadia Hall crowd stirred with anticipation, Thompson started lashing out at the members of the Chicago press who had opposed him from the start of his career. All but the two Hearst papers—the American and the Herald and Examiner—had been consistently antagonistic to his administration, but his wrath was concentrated on the two major Chicago dailies: the Chicago Daily News, under its owner-publisher Victor F. Lawson, and the Tribune, run by Colonel Robert R. McCormick. To Thompson, these were the “lying, crooked, thieving, rotten newspaper editors”; they were the “great cancer gnawing at the very heart of our city of Chicago.” Calling them “crooks” and “hypocrites,” he claimed that they used their enormous influence “to destroy men in public life, men who had the courage to fight for the people!”

But Lawson and McCormick were not alone in their perfidy. There were other villains afoot in the city, such as the tack-head academics at the University of Chicago, the corrupt Democrats on the city council, and the treacherous reformers of the Municipal Voters’ League, an alleged civic watchdog organization that had been especially hard on Big Bill’s administration. All of them opposed the mayor because all of them were merely instruments of the “sinister interests.” They were beholden, in other words, to the rich utility barons, who wanted to gouge the people with high gas and electricity rates, and to the rich traction barons, who wanted to bleed the people dry with high fares for streetcars and L trains. Those sinister interests, in fact, were the true enemy in the war against the people of Chicago. “Gold is their God!” the mayor proclaimed. And to get their gold, they had “betrayed and sold out the people!”

Fortunately, however, the people had a champion to defend them against those who schemed to get rich at the public expense. “The People’s David” wasn’t afraid to stand up against the interests. He had done so numerous times over the past four years, taking up arms against rotten traction ordinances, venal school officials, and the meddling of corporate lawyers in city affairs. Wasn’t that the kind of mayor they wanted to lead Chicago forward to its “wonderful future”—someone willing to do battle for the common people? “I fought,” the mayor cried, as applause once again echoed through the hall. “I fought for weeks and months to protect you!”¹⁵

*   *   *

The first step in Lundin’s grand plan was to get Big Bill Thompson into the mayor’s office. The Poor Swede was convinced that this was possible—as long as his protégé did exactly as he was told. As the Trib would later put it, Thompson was to be the mouthpiece, while Lundin would supply the song. And so the two became an inseparable team. Big Bill made the speeches while the Poor Swede worked behind the scenes, calling in favors, making promises, patching together coalitions from the numerous factions that always fought for influence in this hugely heterogeneous city. The Republican Party was in disarray at this time—not just in Chicago, but in the whole country, torn apart by the rift between Roosevelt progressives and Taft party regulars. But Lundin was tireless, willing to compromise, and supremely well organized. Working with his soon-to-be notorious card files (containing records of favors owed and favors promised), he soon assembled the base of support necessary to put Thompson on the ballot for the Republican primary.¹⁶

On December 22, 1914, Thompson stood before a packed house at the Auditorium Theatre in the Loop. Onstage beside him stood a Christmas tree adorned with signature cards of 142,111 Chicago citizens, all of them ostensibly committed to sending Big Bill to city hall. Thompson feigned reluctance at first, but as he later said, in his best cowboy drawl: “I could no longer hold out agin ’em.” Just as he would do some four years later at Arcadia Hall, the big man announced his candidacy for mayor.

At first, most people scoffed at the idea. Without the backing of an established political machine, they said, Thompson wouldn’t even make it through the primary. Even when—thanks in part to an all-out effort to win the city’s African American vote—he eked out a narrow victory to become the official Republican candidate, few doubts were shaken. Opponents were quick to point out that the hard-fought Democratic primary, won by Cook County clerk Robert Sweitzer, had attracted 50 percent more voters than its Republican counterpart. With so much of the town voting for the party of President Woodrow Wilson, everyone expected Sweitzer to run away with the election.¹⁷

Any less sanguine candidate than Thompson might have lost heart. The obstacles before him seemed insurmountable. Most of the city’s newspapers, having initially discounted his candidacy, grew downright hostile once they realized that a creature of the disgraced Lorimer might actually have a chance to become mayor. Thompson was “simply impossible,” stewed Victor Lawson of the Chicago Daily News. Big Bill’s opponent was equally dismissive. “Just who is this Bill Thompson?” Sweitzer complained. “I find he is a man who plays with sailboats.”¹⁸

But while newspapers and political rivals jeered, an awful lot of regular Chicagoans seemed to like what they saw of Thompson on the hustings. For one thing, the man was an entertaining campaigner, always free with a joke or a gibe. And he knew the value of a campaign promise. Just about every voter heard from his lips an appealing pledge: To women, Bill promised a mother on the board of education; to blacks, he promised respect and equal opportunity; to workers, jobs on his big building projects; and to everyone else, an honest administration, a full dinner pail, and a cleaned-up city. He emphasized the bread-and-butter issues that would come to be a hallmark of his later campaigns—reduced gas rates, preservation of the five-cent car fare, greater home rule for Chicago. And always, the emphasis was on boosting the city he loved to a brighter future: “You’re going to build a new Chicago with Bill Thompson!”¹⁹

On Election Day—following Lundin’s dictum, “When in doubt, give a parade”—the Thompson forces hired extras from a circus menagerie to march through the city streets. The animals included three elephants, a bull moose, and a donkey (symbolizing the candidate’s hoped-for appeal to Republicans, Progressives, and Democrats). The electorate seemed to take the hint. When the ballots were counted, Thompson stunned everyone by staging a landslide victory, winning by no fewer than 147,477 votes—the largest victory margin of any mayoral candidate in Chicago history.

“Hoorah for Bill!” cheered an incredulous Gene Pike that night at Thompson headquarters. Jim Pugh, meanwhile, danced around the room, yelling: “Bill, you’re the greatest sonofabitch Chicago ever saw!”

But Thompson himself knew just whom to thank for his victory. “Fred, you’re a wizard,” he said to Lundin, heartily shaking his mentor’s slender hand. “You did it all, and I’m not ever going to forget this!”

William Hale Thompson—surpassing low expectations yet again—had become the forty-first mayor of the city of Chicago. “In six months,” quipped Tribune columnist Bert Leston Taylor, “we’ll know if it’s Big Bill or Big Bull.”

It actually took more like three.²⁰

*   *   *

After about an hour of fiery oratory, Big Bill finally started bringing his speech to a close. In that hour he had given his Arcadia Hall audience just the show they’d been looking for. He had lambasted his enemies in no uncertain terms; he had roared, whispered, crooned, and bellowed; and he had put the upcoming vote in terms easy to understand—as a fight “between the people, on the one hand, and the corporate interests, on the other,” a story with good guys, bad guys, and a massive conspiracy to confuse the electorate about which was which.

And so he made his final plea: “If continued in the office of mayor of Chicago by the suffrage of the people,” he concluded in grand style, “I shall go on yielding to their influence only. I shall sink personal and political considerations in seeking the good of the city. And I shall give myself unreservedly—henceforth as heretofore—to the support of Law, Liberty, and Justice!”

The band broke out with a rousing rendition of “The Star-Spangled Banner” as Big Bill, smiling his beaming, gap-toothed smile, waved his cowboy hat at the crowd and then strode off the stage. Anyone looking for signs that the audience was not 100 percent behind their mayor would have been hard-pressed to find any. According to one report, “the audience stood on its feet, and on the chairs, and cheered and sang” for their candidate. Fred Lundin—looking on, one supposes, from some inconspicuous corner of the hall—could not have been anything but pleased. His great plan had faltered once or twice since he first lifted Thompson from obscurity, but now his efforts were definitely back on track. “A Mayor, a Governor, a President”: There was still a long way to go to achieve all of those goals, but winning for Thompson a second term in office—despite the rabid opposition of their numerous enemies—would be the vital next step.²¹