Election Special: Chicago’s Worst of the Worst

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A photo of a ferris wheel full of KKK members
Corrupt Illinois Governor Len Small was a longtime friend of the Ku Klux Klan, allowing them use of state facilities for robe initiations and cross burnings. This bizarre picture shows the hooded hoodlums enjoying a day at the fairgrounds.

It’s almost over. After what feels like an endless campaign season, no matter who wins, thank heavens above, it’s almost over. Actually, there’s something else to be grateful for: that none of the candidates in this election have sunk to the level that Chicago’s politicians set a century ago.

Oh, we know what you’re thinking. But take our word for it—Washington, DC in 2020 has nothing on the Prairie State in the 1920s. Still don’t believe us? Then allow historian Jim Ridings to introduce you to a rogue’s gallery of some of the most crooked, corrupt, and damnable pols ever to hold public office—including those openly endorsed by the Ku Klux Klan. All these images come from Ridings’ book Chicago to Springfield: Crime and Politics in the 1920s, and if your blood pressure suddenly spikes, don’t say we didn’t warn you.

Bill Thompson posing in a chair reading a newspaper
Big Bill Thompson was a colorful character who amused and outraged people at the same time. During World War I, Thompson was pro-German and anti-British. He once promised to hold a book burning on the shores of Lake Michigan for books of British history. He promised to punch the king of England “in the snoot” if he ever came to Chicago. While out of office in 1924, Thompson set sail on a “scientific” expedition to search for tree-climbing fish in the South Seas; his boat did not even get to the Mississippi River. Thompson held a debate between himself and two live rats, which he used to portray his opponents, in the 1927 election. Thompson is credited with coining the Chicago term, ‘Vote early and often. Image sourced from Chicago to Springfield: Crime and Politics in the 1920s.
Photo of William Lorimer
William Lorimer was elected to Congress in 1894 and then to the U.S. Senate in 1909. In those days, senators were chosen by the state legislature, not by the popular vote. It was proven that Lorimer spent about $100,000 to bribe several state legislators to vote for him. The U.S. Senate held hearings and decided that Lorimer won his seat by “corrupt practices” and threw him out of office in 1912. Lorimer made his comeback into public life when Big Bill Thompson took office as Chicago’s mayor in 1915, and he helped build the Chicago Republican machine bigger than ever. Image sourced from Chicago to Springfield: Crime and Politics in the 1920s.
Will Colvin (left), Governor Small (center), and Chauncey Jenkins (right) photographed together during Small's trial in Waukegan.
With Mayor Thompson’s police on gang payrolls, and Thompson’s wide-open town policy for gangsters and bootleggers, organized crime was further aided by Governor Small’s pardon and parole policy. Small’s pardons had been scandalous from the beginning. The matter blew up into a huge scandal in 1926, when it was revealed the Small administration had been operating a pardon mill. For a price, anyone could buy his or her way out of the penitentiary. Spike O’Donnell and Bugs Moran paid their bribes and were able to get their gangs back together to commit more mayhem on the streets of Chicago. The scheme was headed by Will Colvin (left), supervisor of paroles, and Chauncey Jenkins (right), director of prisons. They are pictured here with Governor Small during Small’s trial in Waukegan. Image sourced from Chicago to Springfield: Crime and Politics in the 1920s.
A photo of Edward Curtis.
During Len Small’s term as state treasurer from 1917 to 1919, he and state senator Edward Curtis operated a money-laundering scheme that netted them about $2 million. Small deposited half the state’s money across 350 banks, and the other half he deposited in just one bank—a bank that did not exist. Curtis owned Grant Park Trust and Savings Bank. He set up a sham operation called the Grant Park Bank. This bank had no furniture, no vault, and no building. It existed only on paper for the purpose of defrauding the state. Curtis loaned money to the Swift and Armour packing houses at six to eight percent interest, paid the state two percent interest, and kept the difference for himself and Small. Image sourced from Chicago to Springfield: Crime and Politics in the 1920s.

Related: Mike McDonald: Chicago’s King Schemer

A headshot of Will Colvin
Will Colvin, chairman of the pardons and paroles board, boldly solicited bribes. Mrs. F. J. Haveland told a grand jury investigating the scandal that Colvin asked her for money if she wanted her son paroled. Governor Small also testified before the grand jury. The scandal became so hot that Colvin was forced to resign. Small then appointed him to the Illinois Commerce Commission at a high salary. Image sourced from Chicago to Springfield: Crime and Politics in the 1920s.
A photo of Frank Leslie Smith
Frank Leslie Smith was appointed by Governor Small as head of the Illinois Commerce Commission in 1921. Smith used his position to shake down the heads of the utility companies he was regulating (including taking $125,000 from Samuel Insull). Smith used that money to run for the U.S. Senate in 1926, which he won. But the Senate decided that Smith bought his seat by corrupt practices, and it refused to admit him. Missouri senator Jim Reed, who chaired the hearings, said, “If this man is to be seated, let us hang over the door of the Senate, ‘Seats For Sale.’ Image sourced from Chicago to Springfield: Crime and Politics in the 1920s.
Governor Len Small standing with his fist raised in the air in defiance.
A defiant Gov. Len Small poses for the camera. When Len Small was indicted for his theft as state treasurer, the governor had his lawyers argue in court that he was immune from prosecution based on an old English doctrine that “the king can do no wrong.” His defiance was answered by a judge who said there was no king in Illinois and that Small would have to stand trial. Image sourced from Chicago to Springfield: Crime and Politics in the 1920s.

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