Report of the President's Commission on the Assassination of President John F. Kennedy

Chicago Labor Union Activities

Ruby became involved with Local 20467 of the Scrap Iron and Junk Handlers Union around 1937, working as a union organizer until early 1940. His close friend and attorney Leon Cooke served as the local’s financial secretary until Cooke was shot by union president John Martin in December 1939; Martin was acquitted on self-defense grounds. Devastated by Cooke’s death, Ruby left the union and adopted the middle name “Leon” in his memory. An AFL-CIO investigation in 1956 found no evidence linking Ruby’s union activities to Chicago’s criminal element, and employers and longtime members attested to the union’s good reputation during his tenure.

Chicago Subsequent Employment

In 1941, Ruby and Harry Epstein organized the Spartan Novelty Co., which sold cedar chests containing candy and punchboards in northeastern states. Returning to Chicago, Ruby continued his mail-order punchboard business and attempted to sell “Remember Pearl Harbor” commemorative plaques, though perfectionism delayed production until the market was saturated. He also sold busts of Franklin Delano Roosevelt and worked for Globe Auto Glass Co. and Universal Sales Co. in 1942-43. Despite his patriotic-themed ventures, friends reported Ruby had no genuine political interest, though he greatly admired Roosevelt.

Chicago Other Activities

Ruby maintained an active social life, entertaining Virginia Belasco on weekends during a New York trip and cultivating a “ladies’ man” reputation. He joined friends in disrupting German-American Bund rallies for ethnic rather than political reasons, sometimes physically fighting Bund members. While temperamental, his violence was generally limited to intervening against perceived unfairness, such as fighting students who insulted a Black piano player or a man abusing an older woman. He maintained friendships with boxer Barney Ross, frequented Marigold Gardens and the Lawndale Poolroom, and worked out at athletic clubs. Despite his participation in various questionable activities, the evidence did not demonstrate significant organized crime affiliations, as nearly all his Chicago friends denied such connections.