Yes, several — the GOP was the party of Lincoln, after all — but it’s been nearly a century. Chicago’s last Republican chief was William Hale “Big Bill” Thompson, who served from 1915 to 1923, then from 1927 to 1931. He was best known for his isolationism, his feud with Britain’s King George V (whom he once vowed to punch in the “snoot” if he ever came to Chicago), and his alliance with one Al Capone.

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’s campaign. In return, after Thompson was reelected, the mayor didn’t interfere with the gangster’s operations.

The wildest days of Chicago’s Roaring Twenties took place under Thompson’s watch, including the St. Valentine’s 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’t had another Republican since.

Send your questions about the Chicago area to emcclelland@chicagomag.com.