After being elected to two consecutive terms as Mayor in the 1910s, William Hale Thompson sat out of the 1923 election and turned his talents to hobbies that didn't involve bastardizing the integrity of the office of Mayor(I'm sorry, what am I talking about? This is Chicago, the office of Mayor never even had a drop of integrity to start with!) This mostly involved running a boilerplate philanthropic venture whose only real purpose was to jeep his name in the papers.
But by 1927, Big Bill was looking around and was in absolute disgust at the lack of brazen corruption at City Hall, so he threw his hat into the ring. Backed by both the booze-laden dreams of Chicagoans, as well as a totally OVER the table donation of $250,000 from one Alphonse Capone, Thompson beat the reform candidate by a slim margin, and embarked on his mission to make Chicago so wet that people started looking around for an ark. This was all going along so well, bit then the 1928 Primary rolled around, and Thompson was forced to wage war against reformist voices from within his own Party. This faction was led by Senator Charles Deneen, who(while not running himself either) had had a rivalry with Thompson for almost 25 years. Thompson controlled every elected office in the city, county, AND state(save for one) and he wanted to keep it that way.
One key office that was up for grabs was that of Cook County State's Attorney, in charge of prosecuting corruption cases in the city. Thompson's man was the incumbent, and his re-election was of vital importance to Thompson. Thompson's neck was on the line this time(both literally and figuratively), so he did what any rational, level-headed, democratically-minded politician would do: he declared open War against Deneen's faction and anybody else who got in his way. In the six months prior to the primary, there were 62 bombings in the city, taking the lives of two politicians. At the time, a popular slang term for a grenade was a "pineapple", thus earning the 1928 contest the nickname "Pineapple Primary". Things got so bad that 3,000 local lawyers were deputized as poll watchers, with the power to have any malfeasance reported to the police and have the perpetrators arrested(at the same time, a federal grand jury was sworn in to protect the voting rights of the citizenry). In the end, Thompson would serve only 3 more years before being bounced out of office by Anton Cermak, but he would leave a legacy of corruption and thuggery that would follow him to this day.
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