Born Jacob Leon Rubenstein in Chicago sometime in 1911 — his exact birthdate is under some question — Ruby survived a troubled and violent upbringing that included several run-ins with the police and constant exposure to the criminal element of the city. He served in World War II, was discharged from the service in 1946, and moved to Dallas with his brothers in 1947.

There, Ruby became known as a hot-headed nightclub owner and a friend to the police who frequented his places. By 1963, Ruby had tried on a string of business ventures, none of them very successful. When an “upscale” place called the Sovereign Club failed to flourish, he rebranded it as the Carousel Club, a burlesque spot that featured champagne, beer, pizza, a band and a handful of strippers.

“[Ruby] described the Carousel Club as a ‘f–ing classy joint’ and patrons who challenged his opinion sometimes got thrown down the stairs,” Gary Cartwright wrote in Texas Monthly in 1975. “The Carousel was a dingy, cramped walk-up in the 1300 block of Commerce, right next to Abe Weinstein’s Colony Club and close to the hotels, restaurants, and night spots that made downtown Dallas lively and respectably sinister in those times of official innocence.”

According to several oral histories conducted by the Sixth Floor Museum, Ruby’s definition of “classy” and “professional” was sometimes stretched. He often approached young women on downtown streets to entice them into appearing as amateur strippers in his club.

“Ruby never seemed to be about quality in terms of business, and yet, personally, he tried to keep fit, he ate a good diet, he always dressed very nicely. Always wore a suit and really wanted to ingratiate himself with reporters, with police officers,” Fagin says. “So while he cared a lot about his physical appearance and his personality — he was very sociable — when it came to business, he seemed kind of clueless in terms of what constituted class.”

After the Kennedy assassination, many conspiracy-minded theorists pointed to Ruby’s involvement in nightclubs and his rough childhood in mob-run Chicago as evidence that he was involved in organized crime and used that to push the idea that the killing of Kennedy was mob-backed.

Ruby had made at least one trip to Havana, Cubatoo, which raised more organized crime suspicions. But by most accounts, Ruby was just not that connected.

“He was always adjacent to criminal activity, if not involved in it personally. It’s believed he enjoyed giving people the impression that there was far more to him than there was in reality,” Fagin says. “Certainly, it helped his club business for people to think that, oh, they’re rubbing elbows with a gangster. And Ruby did not dissuade them of that.”

Through the years, Ruby’s ties to organized crime have been difficult to prove. Still, a mostly failed nightclub owner who, at the time of the Kennedy assassination, owed the government more than $4,500 (some $38,500 today) — and who had made mysterious trips to Communist-run Cuba — seems prime fodder for those that suggest Ruby silenced Oswald as part of some larger mob-involved conspiracy to kill Kennedy.

But other explanations for Ruby’s actions Nov. 24, 1963 — some in his own words — counter that notion.

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