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.

Military Activities (1943-46)

Jack Ruby, originally classified 1-A in September 1941 and reclassified as 1-H or 3-A due to age or financial hardship, was reclassified 1-A again in early 1943 and inducted into the U.S. Army Air Forces on May 21, 1943, becoming the last of the Rubenstein brothers to enter military service. After completing basic and advanced aircraft mechanic training at various southern airbases (with a brief five-week stint at Farmingdale, New York), he earned a sharpshooter’s rating with the M1 carbine in February 1944, received consistently excellent character and efficiency ratings, attained the rank of private first class, and was honorably discharged on February 21, 1946. Ruby was reportedly quick to respond to anti-Semitic insults, at one point beating a sergeant who called him a “Jew bastard,” and while his military work ethic drew conflicting assessments, the record contained no indication of anti-American sentiment. He openly admired President Roosevelt, reportedly weeping upon learning of the president’s death in April 1945, and continued small-scale entrepreneurial ventures while in the service, peddling punchboards and chocolates sent from Chicago and enjoying card and dice games near the barracks.

Postwar Chicago (1946-47)

After his discharge, Ruby joined his brothers in Earl Products Co., which manufactured cedar chests, punchboards, and small aluminum goods, with Jack handling sales. Insufficient profits led to frequent arguments, and Hyman left the company early. Jack sold costume jewelry alongside Earl Products merchandise and refused to travel outside Chicago, leading Earl and Sam to buy out his interest for over $14,000. Despite some reports, it was unlikely he was in the nightclub business—he may have been confused with Harry Rubenstein, who operated such establishments and was convicted of manslaughter. His personality remained largely unchanged: fashionably dressed, soft-spoken but hot-tempered, quick to fight anti-Semitic or anti-military insults, and active at athletic clubs with a reputation as a “Romeo.”

Dallas (1947-63)

Ruby established permanent residence in Dallas in late 1947, having initially visited to help his sister Eva Grant manage the Singapore Supper Club. He reported returning to Dallas at Eva’s request, though he later stated his Chicago “merchandising deals” had failed. His sister had visited Dallas during World War II and arranged financing from her brothers for the nightclub. The move was likely motivated by the failure of his Chicago business and his separation from Earl Products. Ruby became the operator of the Singapore Supper Club, which during Paul Roland Jones’ appeal was frequented by Jones and other criminals.