![\"Illustration](\"https:\/\/www.europesays.com\/us\/wp-content\/uploads\/2025\/10\/C202304-City-of-Big-Questions-illustration-2.jpg\")
Illustration: Greg Clarke<\/p>\nIllustration: Greg Clarke<\/p>\n
Yes, several\u2009\u2014\u2009the GOP was the party of Lincoln, after all\u2009\u2014\u2009but it\u2019s been nearly a century. Chicago\u2019s last Republican chief was William Hale \u201cBig Bill\u201d Thompson, who served from 1915 to 1923, then from 1927 to 1931. He was best known for his isolationism, his feud with Britain\u2019s King George V (whom he once vowed to punch in the \u201csnoot\u201d if he ever came to Chicago), and his alliance with one Al Capone.<\/p>\n
Thompson was defeated in 1923 by a Democrat, William Dever, who shut down thousands of speakeasies across the city. But after four years, Chicagoans were tired of reform. They wanted beer. Capone donated at least $100,000 to Thompson\u2019s campaign. In return, after Thompson was reelected, the mayor didn\u2019t interfere with the gangster\u2019s operations.<\/p>\n
The wildest days of Chicago\u2019s Roaring Twenties took place under Thompson\u2019s watch, including the St. Valentine\u2019s Day Massacre. On the positive side of his legacy, Thompson was a supporter of Oscar Stanton De Priest, who was the only Black member of Congress when he was elected in 1928. Overall, though, a 1993 survey of historians ranked Thompson the worst big-city mayor in American history. No wonder we haven\u2019t had another Republican since.<\/p>\n