The Pineapple Primary was the name given to the primary election held in Illinois on April 10, 1928. The campaign electoral contest was marked by numerous acts of violence, mostly in Chicago and elsewhere in Cook County; more than 60 bombings occurred during the campaign, and at least two politicians were killed. The name derives from the slang description of a hand grenade as a "pineapple". Underlying the violent campaign was the lucrative Prohibition-era bootlegging trade, a corrupt city government, and politicians with ties to organized crime. 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.[1]
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The Pineapple Primary took place during the administration of the notoriously corrupt Chicago Mayor William Hale ("Big Bill") Thompson, a Republican. Thompson had campaigned for a wide open town in the 1927 mayoral election and bested reformer William E. Dever in Dever's bid for a second term as mayor. Once elected, Thompson turned the city's resources away from fighting the bootleggers and toward fighting those who advocated reforming the city government. Thompson had the support of mobster Al Capone and, significantly, was alleged to have accepted a $250,000 contribution from the gangster toward his campaign.[2][3]
Thompson was part of one faction of the state Republican Party. Other key players allied with "Big Bill" included Governor Len Small, and State's Attorney for Cook County Robert E. Crowe. Both Small and Crowe were vying for a primary victory that would lead to them being the Republican candidate on the ballot in the November general election. Crowe — was described in one news account as "the overlordship of Chicago crime and vice."[4][5]
The competing Republican faction — considered less corrupt than the Thompson faction, but also less effectively organized — was led by U. S. Senator Charles Deneen, and included Louis Emmerson, incumbent Secretary of State who was battling Small for the 1928 Republican nomination for governor, and John A. Swanson, then a Circuit Court judge in Cook County, who opposed Crowe for State's Attorney for Cook County in the 1928 primary. Neither Thompson nor Deneen themselves were standing for election to their respective offices during the 1928 primary.[5]
On March 21, Giuseppe "Diamond Joe" Esposito, the Republican ward committeeman for the 25th Ward. Esposito, a leader of his ward's Italian community, and linked to organized crime, was shot and killed on the street near his home at 800 S. Oakley Blvd. According to contemporary accounts, Esposito was reputed to provide protection for gamblers and was tied to bootlegging as well as shootings and bombings, but also Esposito had friends among the city and state governments.[6]
Esposito had received repeated warnings that he was marked for death unless he fled Chicago. Esposito was struck down after a day of campaigning within sight of his home while in the company of his bodyguards. While passing the house at 806 S. Oakley Blvd., a volley of shots rang out from a passing automobile. The shots were heard by Esposito's wife, who ran the hundred feet from her home to the side of her dying husband. Two double-barrel shotguns and a revolver were found at the crime scene.[6]
Neither of his bodyguards were struck — they dropped to the ground at the first sound of shots — and police suspected that Esposito may have been set up by his bodyguard. Shortly after Esposito's slaying, a witness to the murder was found shot to death. No one was ever charged with Esposito's killing.[6]
On the night of March 26, a bomb went off at the residence of U. S. Senator Charles S. Deneen at 457 W. 61st Place, damaging the front porch and breaking windows in the Deneen house and elsewhere in the vicinity. Deneen was not home at the time of the blast, having departed for Washington, DC by train earlier in the day after attending Esposito's funeral. Deneen and Esposito were political allies despite Deneen's reputation as a political reformer.[7] Almost at the same time as the Deneen house was bombed, a bomb was thrown at the residence of a Deneen ally, Circuit Court Judge John Swanson, a candidate for state's attorney. The bomb was tossed at Swanson's home at 7217 Crandon Ave. as the judge returned home, causing severe damage but narrowly missing Swanson.[7]
On the day of the primary, Octavius C. Granady, a candidate for committeeman in the 20th ward, was chased in his car and killed.[8]