at the start of the 20th century, there was a millionaire in the Chicago North Shore area (in Winnetka) named Willam Bross Lloyd (son of the newspaperman and philanthropist Henry Demarest Lloyd), who helped to fund the Socialist Party and ran for U.S. senator as a Socialist in 1918. He was tried in 1920 for being a communist as a result of the Palmer Raids (he one of the organizers of the Communist Labor party in America) and defended by Clarence Darrow.
There's a statue of him, hidden behind some bushes, with a socialist slogan on it. I think it may be "workers of the world unite!"
There's also a beach named after his family. -- Jim Devine / "There can be no real individual freedom in the presence of economic insecurity." -- Chester Bowles