by Gary Krist
Then, on January 6—as if to underline the passing of the old to make way for the new—the city learned that former president Theodore Roosevelt had died unexpectedly at his Sagamore Hill home. Shocked, Chicago went into mourning. Local dignitaries such as Jane Addams and Clarence Darrow published encomiums to the great man in the newspapers. Two days later—at 1:45 p.m., the exact time of Roosevelt’s funeral—all business throughout the city stopped for five minutes. Streetcars and elevated trains shut down; schools and factories suspended operations; crowds gathered on street corners for a moment of silence. For three hundred seconds, the “mighty, roaring, sweltering, pushing, screaming, magnificent, hideous steel giant that was Chicago” came to a standstill.
And then it started up again as before, and moved on.8
Chicago was, in any case, more preoccupied with the future than with the past. The “youngest great city in the world” had important business to attend to—in particular, the upcoming mayoral election. In April voters would have to decide who would lead the city through its “greatest year” ahead. And that decision would ultimately amount to a referendum on the incumbent, the controversial figure who, for better or worse, had come to represent Chicago in the public mind both in the United States and abroad. Though many different candidates would compete in the race, all eyes would be on the current occupant of city hall: the blustering, flamboyant, unscrupulous, but always entertaining political phenomenon known to all as “Big Bill”—Chicago’s mayor, William Hale Thompson.
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 f
ounding 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 savvi
er 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
