Background
The Pineapple Primary took place in 1928, during the administration of the notoriously corrupt Chicago Mayor William Hale ("Big Bill") Thompson, a Republican. Thompson had served two corruption-marred terms as mayor in 1915 and 1919. Following exposure of several scandals tied to his machine, Thompson sat out the 1923 contest, with the result that reformer William E. Dever, a Democrat, was elected mayor.
After four years away from City Hall, Thompson cast his hat in the ring for the 1927 mayoral campaign, capitalizing on public displeasure with the zealous enforcement of the Prohibition laws under Dever. The always-bombastic Thompson campaigned for a wide open town, at one time hinting that he'd reopen illegal saloons closed by Dever's police. Such a proclamation helped Thompson's campaign gain the support of mobster Al Capone. Thompson's campaign allegedly accepted a contribution of $250,000 from the gangster. In the 1927 mayoral race, Thompson beat Dever by a relatively slim margin.
Once he returned to City Hall in the spring of 1927, Thompson turned the city's resources away from fighting the bootleggers, and toward fighting those who advocated reforming the city government.
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