Yes. In fact, it’s happened twice. The first murdered mayor was Carter Harrison. On October 28, 1893, two days before the closing of the World’s Columbian Exposition, the 68-year-old former lawyer and real estate baron was relaxing in his mansion on South Ashland Avenue. Harrison, who was midway through his fifth term, always made himself available to the public, and that night, he was visited by Patrick Eugene Prendergast, an Irish immigrant who was angry with the mayor for not appointing him city attorney. Prendergast shot Harrison three times. Despite a defense by the great Clarence Darrow, the assassin was hanged.

The other victim was Anton Cermak, though he wasn’t the intended target. On February 15, 1933, the first-term mayor, 59, was in Miami to meet with President-elect Franklin D. Roosevelt. As Cermak was leaving FDR’s car, an Italian immigrant named Giuseppe Zangara fired on the vehicle. A bystander supposedly hit Zangara with her purse, causing him to miss Roosevelt, but Cermak was hit in the chest. At first, his condition improved, but he developed colitis and died on March 6. The Tribune reported that Cermak told FDR, “I’m glad it was me, not you,” but most scholars today believe he probably didn’t say that — and in any case, surely wasn’t glad at all.

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