While accounts focus on Cermak and the other victims being random casualties of an attempt to assassinate Roosevelt, a conspiracy theory emerged sometime before 1999,<ref name=AllanMay/> originating in Chicago,<ref>{{cite news |last=Kass |first=John |author-link=John_KassJohn Kass |url=http://articles.chicagotribune.com/2013-03-07/news/ct-met-kass-0307-20130307_1_chicago-way-anton-cermak-chicago-politics |title=Cermak's death offers lesson in Chicago Way |work=Chicago Tribune |date=March 7, 2013 |access-date=April 9, 2015 |quote=Chicagoans don't believe in coincidences ... when coincidences involve Chicago politics and the Chicago Outfit }}</ref> asserting that Zangara was a hired killer working for [[Frank Nitti]], who was the head of the [[Chicago Outfit]] crime syndicate. John William Tuohy, author of numerous books on organized crime in Chicago, after reviewing Secret Service records,<ref>{{cite book |last=Russo |first=Gus|author-link=Gus_RussoGus Russo |url=https://books.google.com/books?id=GnCn1u-zHbQC |title=The Outfit: The Role of Chicago's Underworld in the Shaping of Modern America |publisher=[[Bloomsbury Publishing USA]] |year=2008 |pages=92–96 |isbn=978-1596918979 |access-date=April 9, 2015 }}</ref> described in detail in a 2002 article his interpretation of how and why Cermak was the real target and the relationship of the shooting to the rampant gang violence in Chicago.<ref>{{cite web |url=http://www.americanmafia.com/Feature_Articles_200.html |title=The Guns Of Zangara: Part Three of Three |last=Touhy |first=John William |work=AmericanMafia.com |date=March 2002 |access-date=April 9, 2015 }}</ref> The theory is enhanced by numerous researchers, citing their analysis of court testimony, asserting that Cermak had directed an assassination attempt on Nitti less than three months earlier.<ref name=AllanMay>{{cite web |url=http://allanrmay.com/First_Shooting_of_Nitti.html |title=The First Shooting of Frank Nitti |last=May |first=Allan |year=1999 |access-date=April 9, 2015 |archive-date=March 7, 2015 |archive-url=https://web.archive.org/web/20150307120739/http://allanrmay.com/First_Shooting_of_Nitti.html |url-status=dead }}</ref><ref>{{cite web|url=http://www.americanmafia.com/Feature_Articles_197.html |title=The Guns Of Zangara: Part One of Three |last=Touhy |first=John William |work=AmericanMafia.com |date=March 2002 |access-date=April 9, 2015 |url-status=dead |archive-url=https://web.archive.org/web/20130725055310/http://www.americanmafia.com/Feature_Articles_197.html |archive-date=July 25, 2013 }}</ref>
The conspiracy theorists suggest that Zangara had been an expert marksman in the [[Royal Italian Army|Italian Army]] 16 years earlier, who would presumably hit his target,{{sfn|Sifakis|1987|p=}} though sidestepping any issues about Zangara's progressive age and health issues since his time in the war, his short stature requiring him to stand on a jostled chair, his experience being with a rifle rather than with a pistol from a great distance, and his own statements regarding his target.
