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William Hale Thompson head shot
Chicago Mayor William Hale Thompson accepted campaign contributions from gangster Al Capone. Thompson led the faction that supported lax enforcement of Prohibition in the Illinois 1928 Republican campaign
C.S. Deneen LCCN2014716647 (cropped)
U.S. Senator Charles S. Deneen, a former state representative and governor, opposed Thompson's slate. Deneen led the reformist faction in the Illinois 1928 Republican campaign

The Pineapple Primary was the name given to the primary election held in Illinois on April 10, 1928. The campaign was marked by numerous acts of violence, mostly in Chicago and elsewhere in Cook County. In the six months prior to the primary election, 62 bombings took place in the city, and at least two politicians were killed. The term "Pineapple Primary" originates with the contemporary slang term "pineapple" to describe a hand grenade.

Underlying the violent campaign was the lucrative Prohibition-era bootlegging trade, a corrupt city government, politicians with ties to organized crime, and a deep-seated and bitter political rivalry between several of the Illinois Republican candidates. The threat of election day violence was so severe that Chicago's U.S. Marshal requested the U.S. Attorney General for authority to deputize 500 additional federal marshals to assure the electorate to cast their ballots in safety.

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 political organization, 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 into 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 ($4211686 in 2017) 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.

Outcome

The voters sided with Deneen's slate, with all three of his candidates winning the Primary. Louis Emmerson defeated Len Small by 400,000 votes and went on to win the Governor's office. John Swanson defeated Crowe by 120,000. The Tribune attributed his win to Democrats crossing over to vote Republican following the earlier bombings. Otis Glenn defeated Small for the Senate seat. Glenn's victory spelled the end of Smith's convoluted attempts to be seated in the Senate following an earlier appointment that the Senate denied.

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