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Big Bill Thompson — Mayor of Chicago
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Big Bill Thompson ran Chicago twice, from 1915 to 1923 and again from 1927 to 1931, on a platform of loud promises and looser enforcement.
Al Capone reportedly poured $260,000 into his final campaign — and got the wide-open city he paid for. History has not been kind to the verdict.
Quick Facts
Q: When was Big Bill Thompson mayor of Chicago?
A: Twice — from 1915 to 1923, and again from 1927 to 1931.
Q: What was his connection to Al Capone?
A: Capone reportedly contributed roughly $260,000 to Thompson's final campaign in exchange for a loosely enforced city.