Al Capone

===Political alliances===
Chicago politicians had long been associated with questionable methods, and even newspaper circulation "wars", but the need for bootleggers to have protection in city hall introduced a far more serious level of violence and graft. Capone is generally seen as having an appreciable effect in bringing about the victory of [[Republican Party (United States)|Republican]] mayoral candidate [[William Hale Thompson]], who had campaigned on a platform of not enforcing Prohibition and at one time hinted that he'd reopen illegal saloons.<ref name="big_bill_232_244">{{cite book |last=Wendt |first=Lloyd |title=Big Bill of Chicago |year=1953 |publisher=Bobbs-Merrill |location=Indianapolis, IN |pages=232–244 |author2=Herman Kogan}}</ref> Thompson allegedly accepted a contribution of $250,000 from Capone. Thompson beat [[Democratic Party (United States)|Democratic]] candidate [[William Emmett Dever]] in the 1927 mayoral race by a relatively slim margin.<ref name="mayors">{{cite encyclopedia |title=Mayors |url=http://encyclopedia.chicagohistory.org/pages/795.html |encyclopedia=Encyclopedia of Chicago |access-date=January 3, 2012 |archive-url=https://web.archive.org/web/20120101191619/http://encyclopedia.chicagohistory.org/pages/795.html |archive-date=January 1, 2012 |url-status=live}}</ref><ref>{{cite encyclopedia |title=Big Bill Thompson |url=https://www.pbs.org/kenburns/prohibition/media_detail/S0987 |encyclopedia=Encyclopedia of Chicago |access-date=January 3, 2012 |archive-url=https://web.archive.org/web/20111203020602/http://www.pbs.org/kenburns/prohibition/media_detail/S0987/ |archive-date=December 3, 2011 |url-status=live}}</ref>

On the day of the so-called [[Pineapple Primary]] on April 10, 1928, voting booths were targeted by Capone's bomber, [[James Belcastro]], in wards where Thompson's opponents were thought to have support, causing the deaths of at least fifteen people. Belcastro was accused of the murder of lawyer Octavius Granady, an African-American who challenged Thompson's candidate for the Black vote, and was chased through the streets on polling day by cars of gunmen before being shot dead. Four policemen were among those charged along with Belcastro, but all charges were dropped after key witnesses recanted their statements. An indication of the attitude of local law enforcement toward Capone's organization came in 1931 when Belcastro was wounded in a shooting; police suggested to skeptical journalists that Belcastro was an independent operator.<ref>Sifakis, Carl, ''The Mafia Encyclopedia'', 2nd ed., Checkmark Books (1999), pp. 291, 292</ref><ref>Russo, Gus, ''The Outfit'', Bloomsbury (2001), pp. 38, 39</ref><ref>The Evening Independent – January 12, 1931, AP, Career of Chicago bomb king halted by bullets</ref><ref>The Afro American – October 12, 1929, Chicago (ANP)Police Named in Granady Killing,</ref><ref>The Outfit: The Role Of Chicago's Underworld In The Shaping Of Modern America. Gus Russo</ref>

A 1929 report by ''[[The New York Times]]'' connected Capone to the 1926 murder of Assistant State Attorney William H. McSwiggin, the 1928 murders of chief investigator Ben Newmark and former mentor Frankie Yale.<ref>{{cite web|url=https://www.nytimes.com/1929/10/16/archives/capone-is-accused-of-many-murders-but-chicago-policy-decide.html|title=Capone is Accused of Many Murders; But Chicago Policy Decide Statement by Wife of His 'Executioner' Is Myth. Yale Named as One Victim; Receipt of Letters Threatening Exposure of 'Scarface Al' as the Slayer of McSwiggin Denied.|work=[[The New York Times]]|date=October 16, 1929|access-date=January 23, 2021|archive-date=January 23, 2021|archive-url=https://web.archive.org/web/20210123220510/https://www.nytimes.com/1929/10/16/archives/capone-is-accused-of-many-murders-but-chicago-policy-decide.html|url-status=live}}</ref>