AL CAPONE CHICAGO OUTFIT MAYOR BIG BILL THOMPSON POLITICAL CORRUPTION HISTORY IL For Sale

An antique ashtray of Capone\'s corrupt Governor from the high point of Al Capone and the Chicago Outfit. Thanks for looking.

The relationship between William Hale \"Big Bill\" Thompson (the Mayor of Chicago from 19151923 and 19271931) and infamous mob boss Al Capone is widely recognized by historians as one of the most flagrant examples of political corruption and alliance between local government and organized crime in American history. 1. Financial Backing of the 1927 Election After opting not to run for re-election in 1923, Thompson staged a political comeback for the 1927 Chicago mayoral election against the reform-minded incumbent, William Emmett Dever. Al Capone was heavily invested in ensuring a Thompson victory so that his illegal bootlegging, gambling, and prostitution operations could run unbothered. Capone reportedly funneled anywhere between $100,000 and $250,000 directly into Thompsons campaign coffers. 2. Open Campaigning and Public Alliances Unlike politicians who hid their underworld ties, Thompson\'s alliance with Capone was a matter of public knowledge. Thompson ran on a aggressively theatrical \"wet\" platform, explicitly promising voters that he would halt the enforcement of Prohibition and stop local police from looking through windows to catch citizens having a drink. Capone even opened campaign headquarters for Thompson in the city, using the mob\'s muscle to enforce political compliance. 3. The \"Pineapple Primary\" and Voter Intimidation The alliance reached a violent peak during the April 10, 1928 Republican primary, infamously known as the \"Pineapple Primary\" (named after the slang for the hand grenades used by the mob). Capone\'s chief enforcers and bombers targeted voting booths and polling stations in wards where Thompsons political rivals held support. The targeted violence resulted in the deaths of at least 15 peopleincluding Octavius Granady, an African-American lawyer who dared to challenge Thompson\'s hand-picked candidate for the Black vote. 4. City Hall Infiltration Once back in office, Thompson rewarded Capone\'s financial and physical backing by essentially turning a blind eye to the Chicago Outfit. He appointed Daniel Serritella, a known associate of Al Capone, as the city sealer. This appointment effectively placed a Capone agent inside City Hall to oversee the administration\'s activities and protect the mob\'s interests. Under Thompson\'s tenure, Capone was able to operate gambling rings and speakeasies mere blocks away from the Mayor\'s office with absolute impunity. 5. Fall from Power and Legacy The rampant lawlessness and violent headlinesincluding the 1929 St. Valentine\'s Day Massacre gradually soured public opinion against Thompson\'s circus-like administration. In 1931, voters overwhelmingly ousted \"Big Bill\" in favor of Democrat Anton Cermak, effectively ending Thompson\'s political career. The depth of Thompson\'s corruption was fully realized after his death in 1944. Despite earning a modest mayoral salary of no more than $22,500 a year, investigators uncovered safe-deposit boxes belonging to Thompson that were crammed with nearly $1.84 million in cash and securitiesa massive fortune heavily tied to the bribes and payoffs distributed by Capone\'s syndicates. Today, exhibits tracking this era can be explored via resources at the Chicago History Museum.