The announcement was clear: He would resign from office if his candidates were defeated in the Republican Party primary in Chicago. Mayor William Hall Thompson had promised that. But there was harsh criticism of his administration and therefore competition within the party. So Thompson was “helped” by his best allies: the “Chicago Outfit” with Al Capone at the head.
Three days before the election on April 10, 1928 (which traditionally takes place on a Tuesday in the USA), a florist's house was partially destroyed by an explosive device. It was the 31st explosion since the beginning of the year and the 65th detonation since November 1, 1927, which was directed against declared or even possible opponents of the incumbent city leader.
The Republican primary for the official local election in what was then the second largest city in the USA went down in history as the “Pineapple Primary” - “Pineapple” because of the shape of the US Army's standard hand grenade, the Mk. 2, which was at least partially used at the end of the First World War. At its core, it was about the dispute between two wings of the Republican Party.
One grouped itself around Mayor Thompson and the incumbent Governor of Illinois, Lennington “Len” Small. Organized crime in Chicago had bought this Republican faction, sometimes with exorbitant sums of money.
The other wing was led by incumbent Senator Charles S. Deneen, himself governor from 1905 to 1913. He included, among others, Judge John A. Swanson. This group rejected Thompson's candidate because of their proximity to crime boss Al Capone - but at the same time had Giuseppe Esposito, a local politician of Italian origin with close ties to the "mob", in their ranks.
By the fall of 1927 it became apparent that Thompson would have trouble in the primaries. In particular, his candidate for the important position of public prosecutor in Cook County (which the city belongs to) was shaky - he had made himself unpopular with the population through extremely lenient proceedings against gangsters. Now the mayor’s years of support for the “Chicago Outfit” were paying off.
During his first term in office from 1915 to 1923, Thompson had already ensured that the Prohibition decreed by Washington, the complete ban on alcoholic beverages, was only enforced pro forma. Because, among other things, he had no realistic chance of being re-elected by large parts of the electorate, the mayor did not even stand in 1923.
He was succeeded by Democrat William E. Dever. As soon as he was in office, the new man took tough action against the “mob”, but failed due to widespread corruption at all levels of the city and an escalating gang war. In 1927, Thompson replaced his own successor - incidentally financed with Al Capone's support: the gangster provided more than $200,000 for the election campaign.
After his return to city hall, Thompson redirected city policy: instead of fighting alcohol smugglers, advocates of city government reform should be put under pressure. However, there was now headwind in his own party: the city leader's proximity to organized crime repelled many Republicans. Therefore, the opportunities grew for Deneen, Swanson and their supporters.
So Al Capone intervened again: in the last two months of 1927, hand grenades detonated in front of the offices of Deneen supporters and sometimes in bars where this wing of the Republicans met. The number of fire attacks on the streets also increased.
Most Chicago newspapers supported Deneen's reformers. They accused Thompson, Crowe and their supporters of doing too little to combat escalating crime. In fact, none of the bombings had led to a conviction, nor had any of the murders, often on the street. Deneen's supporters promised to improve conditions in Chicago if she were elected.
For their part, Thompson and Crowe accused the Deneen faction of exaggerating the extent of crime. The attacks were not investigated because they were staged: hand grenades were placed in front of and in people's own houses in order to be able to blame the mayor.
On March 21, 1928, Giuseppe Esposito was attacked and killed in a moving car on his doorstep.
Just five days later, on the night of March 27, a bomb exploded in Senator Deneen's home - just hours before he had attended Esposito's funeral. The porch was damaged and windows were broken. Deneen was not at home at the time of the explosion, having left for Washington that afternoon.
Almost simultaneously with the bombing of Deneen's house, a "pineapple" hand grenade flew into the house of John A. Swanson. The explosion caused severe damage but narrowly missed the judge.
From the US capital, Deneen commented that the attacks in Chicago were “the work of organized criminals protected by officials”; they demonstrated their “desperate effort to maintain political control.” Thompson's henchman Crowe, however, was convinced that the bomb had been planted by Deneen's people - "to discredit the mayor and me".
Given both sides' involvement with Al Capone's mob, the Washington Post complained on April 8, 1928 that the Chicago primary was a decision about "which gang would collect the $100 million a year in bribes" from alcohol smuggling and gambling. This leads to an unprecedented brutalization of morals and escalating crime: “A murder of any ordinary person can be arranged for $50, although there is considerable competition as to who gets the job.”
Now the federal authorities sent additional forces to the city on Lake Michigan, including 500 US marshals. Almost 3,000 respected citizens were hired as election observers to prevent manipulation.
Republican Party members finally decided on Deneen's candidate on April 10, 1928: Louis Emmerson defeated Len Small by 400,000 votes and was elected governor of Illinois in November 1928. John Swanson defeated Crowe by a majority of 120,000 votes.
Despite this, William Thompson did not resign but remained in town hall. It wasn't until April 1931 that he resigned at the end of his regular term in office - by then the voters' dislike of the corrupt mayor had become so intense that he lost to the Democrat Anton Cermak. In 1936 he tried again to win back his old office, but only received three percent of the vote.
At the time, his former partner Al Capone was serving a prison sentence for tax evasion on the Alcatraz prison island in San Francisco Bay. In 1939 he was seriously ill and released for good behavior - at the age of 40.
Thompson died in March 1944 at the age of almost 75. Although he had always lived large, two safe deposit boxes registered to his name were discovered after his death, which together contained nearly $1.84 million in cash. Converted to purchasing power, this sum would be equivalent to between 100 and 150 million US dollars today.
Al Capone remained ailing even after his imprisonment and suffered a stroke in January 1947, from which he died shortly afterwards. But the Chicago Outfit continued to thrive after the setback caused by the repeal of Prohibition in 1933. In addition to illegal gambling and prostitution, the import of drugs became a new business area in the 1950s, and from the 1980s onwards their distribution on the streets.
