During the 1927 Chicago primary elections, to be called "The Pineapple Primary", Belcastro launched a bombing campaign against then Mayor William Hale Thompson.
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The Chicago Crime Commission releases its first published report of those "who are constantly in conflict with the law" naming over 28 underworld figures as public enemies including James "Mad Bomber" Belcastro, Edward O'Donnell, James "Fur" Sammons, William "Three Fingers" White, Jake Guzik, and Al Capone.