The Pineapple Primary: An Election Violence Threat That Required 500 Federal Marshals
Chicago has a long history of corrupt politics and organized crime, and tensions between two groups vying for control of the city (and a slice of its bootlegging profits) came to a head during the April 1928 Republican primary election, A.K.A. the "Pineapple Primary." It was full of voter intimidation, bombs, hired thugs, corrupt cops, and a heavy dose of Al Capone.
Big Bill v. Charles Deneen
Between 1915 and 1923, Chicago had been led by the Republican Mayor William "Big Bill" Thompson. During his tenure, he was embroiled in scandal after scandal, and despite his powerful political allies, he was forced to sit out the 1923 election. The race was won by Democrat William Dever, who wanted to reform the city with strict enforcement of Prohibition laws. As such, neither freedom-loving Republicans nor the city's organized crime bosses were big Dever fans, so they teamed up like an alcoholic Justice League to get Big Bill back in office.
Once he was back on his throne, Thompson set his sights on seizing control of the Illinois Republican Party, but first, he had to get through his longtime rival, Senator Charles Deneen. The pair had a contentious relationship dating all the way back to 1904, when they clashed at the state convention. By 1928, they had split the Illinois Republican Party into two factions, each of which ran their own candidates for the offices up for grabs in that year's primary election.