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.
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The Pineapple Primary took place in 1928, during the administration of the notoriously corrupt Chicago Mayor William Hale ("Big Bill") Thompson, a Republican.
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During the 1927 Chicago primary elections, to be called "The Pineapple Primary", Belcastro launched a bombing campaign against then Mayor William Hale Thompson.