Jack Ruby: The Many Faces of Oswald’s Assasin

By | May 17, 2024
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Mugshot of Jack Ruby.

After he fired a fatal bullet into Lee Harvey Oswald’s belly and police knocked him to the floor, the shooter asserted, as if startled by the rough handling: “You all know me! I’m Jack Ruby! You all know me!”

In the demimonde of downtown Dallas, where Ruby ran a burlesque joint, and around the courthouse where the shooting occurred, he was a colorful if controversial presence—a pugnacious, impulsive attention-seeker, as ready to slap backs as to punch noses. Now, suddenly, Ruby acquired universal notoriety. He had squeezed the trigger in front of network cameras recording Oswald’s transfer to a different jail just 47 hours after the prisoner allegedly assassinated President John F. Kennedy. Ruby’s action prevented a thorough investigation of Oswald and injected plausibility into conspiracy theories that have continued to flourish for six decades, building on the suspicion that Ruby silenced Oswald to protect whatever malign force wanted Kennedy dead—Castro, the Kremlin, right-wing fanatics or the mob. (With the last of these, Ruby had at least tenuous connections.) 

In Jack Ruby: The Many Faces of an Assassin, Danny Fingeroth doesn’t seek a definitive rebuttal to the conspiracy theories. But he concludes that “Every narrative beyond ‘lone nut’ becomes impossibly unlikely” when Ruby’s personal saga is understood. Fingeroth, a social historian specializing in Jewish American culture, brings Ruby the person to life in his new book. It’s a fresh look at the tragedy that shook the nation 60 years ago but for most Americans today is a hazy historical artifact. 

Jacob Rubenstein was born in Chicago in 1911, the fifth of ten eight offspring produced by Ashkenazi immigrants Joseph and Fannie. Joseph was a hard-drinking carpenter, often out of work and in the beds of other women. He and Fannie  fought frequently, living apart for periods, and Fannie spent stints in a psych ward. That forced the younger kids into foster homes. A frequent truant, Jacob dropped out of high school at 16.

The Jewish enclave around Maxwell Street produced its share of overachievers. Jacob’s contemporaries included Arthur Goldberg and Benny Goodman. His bestie, Beryl Rossofsky, became Barney Ross, aka “Pride of the Ghetto” in sports pages, a champion in three weight divisions. While still teenagers, Jacob and Beryl duked it out with kids from the nearby Italian neighborhood. Later Jacob scalped tickets to some of his pal’s fights. After several years of scrounging for a living, he followed his sister Eva to California, shuttling between Los Angeles and San Francisco, working as a singing waiter, a door-to-door subscription peddler and in other marginal occupations. 

His luck improved on returning to Chicago in 1937 and getting a job with the Scrap Iron Handlers Union. The title was organizer but in fact he was a shtarker, employed to intimidate the local’s adversaries. On his own time, he teamed up with other Jewish toughs to break heads at meetings of the German American Bund. Though secular at that stage, Jacob had a history of violent reaction to any show of antisemitism. His fists would fly, Eva once said, if anyone used a term like “kike.” Pro-Nazi groups warranted an organized response. Jack’s brother Hyman later proudly recalled getting compliments from friends on his kid brother’s anti-fascist exploits because “he just goes in there and breaks up the joint.”

By then Jacob called himself Jack and thought a union career was possible. The local’s founder was a mentor, Leon Cooke, whom Jack admired. But a mob-connected gunman pumped three slugs into Cooke’s back, then was acquitted. So Jack had to exit. He did so with a new middle name: Leon, in memory of Cooke. After army service, he became involved in more marginal business ventures, including a partnership with his three brothers that flopped. In 1947, with scant relevant experience, Jack moved to Dallas, where Eva was struggling to manage a nightspot. 

Exactly why, and on whose nickel, Eva had migrated from California, is still unclear, Fingeroth tells us. One supposition: Gangsters seeking a beachhead in Dallas were responsible. Regardless, it was a life-changing event for Jack. Rubenstein became Ruby because antisemitism was still prevalent in Dallas. He not only took over Eva’s supper club but blossomed into an entertainment entrepreneur who owned, at one time or another, a striptease-cum-burlesque house, two country music venues, a restaurant and a movie theater.

Ruby could be quaintly prudish considering his line of work. He forbade ethnic jokes by comedians. He loudly cursed out a young Gabe Kaplan, later a TV sit-com star, for uttering the word “tits” while auditioning at the Carousel Club, which became his main enterprise. When interviewing prospective strippers, he would insinuate that he expected sex from female employees. But if the woman was agreeable, he refused to hire her. To male pals, he would boast about casual sex with women he picked up elsewhere. 

In fact, Ruby’s sexuality was uncertain. He never married or had a known romantic partner. For several years he frequently saw a woman, a white-collar office worker, but the real nature of their relationship was unclear. Still, he suggested they consult a Reform rabbi about her possible conversion to Judaism. Ruby thought Gerald Klein would be more sympathetic than his own rabbi, Hillel Silverman, of the Conservative synagogue Shearith Israel. Nothing came of their meeting with Klein, and they drifted apart.

Meanwhile, Silverman, later an important source for Fingeroth’s book, was becoming closer to Ruby and two of his siblings, Eva and Sam, both of whom joined the congregation. Shearith Israel was in upscale North Dallas, a world away from the seamy precincts around the Carousel. Ruby managed to be a citizen of both worlds; after the death of his father, he attended services more often and accepted Silverman’s role as mediator in his fractious relationship with Eva. Eager to ingratiate himself with the rabbi, he brought him a dachshund puppy from the latest litter. Ruby loved his dogs to the point of weirdness: He called the pups his children, Silverman told Fingeroth, and their mother his wife. 

If Eva was “a little unstable,” in Silverman’s words, Ruby would become much more so as time passed, and would emotionally implode after he shot Oswald. Silverman would be a close observer of his congregant’s decline. 

For all his diligent promotion efforts, Ruby’s Dallas properties never managed to be consistently profitable. By the time Dallas buzzed over Kennedy’s imminent arrival, Ruby was heavily in debt to the IRS, his brothers Earl and Sam and others. Amidst the stress of potential bankruptcy, Ruby, an avid admirer of the glamorous Kennedy family, fulminated to acquaintances about anti-Kennedy propaganda emanating from right-wing groups. Upon hearing of Kennedy’s death, Ruby was beside himself, closing the Carousel Club for the night and threatening the owner of a competing nightspot with a pistol when he declined to do likewise. 

On the Sunday morning Oswald was to be transferred to a different lock-up, Ruby, wearing his usual dark business suit and fedora, joined the media scrum waiting to record the event. The police took no notice of him as they led Oswald toward the squad car. Ruby managed to shove his .38 Colt revolver into Oswald’s abdomen and fire a single round. 

For a few days afterward, he imagined that all would be well. He savored notes from strangers who praised the vengeance he had wrought. He told the Carousel bartender he’d soon be back at work. To Earl he wrote: “I think we’re going to get a lot of good publicity out of this.” 

Then reality crashed in. District Attorney Henry Wade announced the indictment of Jacob Rubenstein for first-degree murder. Wade would seek the death penalty. To Silverman, Wade denied any antisemitic motive for ignoring the name the defendant had used in Dallas for 16 years. But Bill Alexander, Wade’s senior deputy and Ruby’s long-time acquaintance, later told a reporter: “Ruby was as handicapped as you can be in Dallas. First, he was a Yankee. Second, he was a Jew. Third, he was in the nightclub business.”

Jack’s siblings managed to recruit Melvin Belli, then one of the country’s most famous criminal lawyers, to head the defense team. Belli planned to argue that Ruby had not planned to kill Oswald, or even been conscious of doing so; rather he was in a “fugue state,” his mind blank. But Ruby undermined that strategy by gabbing to jail staffers, visitors, anyone who would listen. He offered various motives for his action: He wanted to spare Mrs. Kennedy the ordeal of witnessing Oswald’s trial. Or he wanted to show that he was “one Jew with guts.” Or he identified with the Kennedy kids because he had grown up without a dad. Or Oswald was simply a “Commie rat” who deserved death. 

Silverman meanwhile began to visit within days of Ruby’s arrest. He delivered a Bible, a prayer book and a sympathetic ear. Soon he was taking detailed notes with a possible book in mind. Silverman later dropped that idea but kept the notes, which he shared with Fingeroth a dozen years ago. They show sharp mood swings before and during the trial, which started the following March. The rabbi observed that Ruby “seemed to be living on multiple planes…and this changing relationship with reality would become increasingly pronounced.” At times he evinced terror spiked with paranoia, as when he told Silverman: “I have unleashed terrible hatred. Now everyone hates Dallas and hates the Jews. This will be terrible for all Jews.”

On March 14 it took the jury only two hours and 19 minutes to bring in a verdict of “guilty of murder with malice” and to impose the death penalty. Ruby’s siblings, with Earl in the lead, did not give up. In the fall of 1965 Earl lured William Kunstler to lead the appeal effort. Kunstler, already a prominent civil rights crusader who vehemently opposed the death penalty, focused the effort on several botched rulings by the trial judge as well as Ruby’s mental state when the shooting occurred. On October 5, 1966, the Texas Court of Criminal Appeals ruled, unanimously, that Ruby deserved a new trial in a new venue, Wichita Falls, starting the following February.

It never took place. Soon after the appeals court decision Ruby was diagnosed with inoperable cancer that had spread to several organs. He died on January 3, 1967, in Parkland Hospital, the same facility in which Kennedy and Oswald had spent their last hours.

Fingeroth does not attempt to evoke sympathy for his protagonist. But he does provide a poignant account of the memorial service in Chicago, attended by the seven siblings and some friends. The rabbi, Davis Graubart, struggled to say something positive. The best he could do was to opine that Ruby “acted as a patriot, but as a misguided patriot and avenger…We dare not condone this act, yet we dare not sit in judgment.” 

Laurence I. Barrett, formerly Time Magazine’s White House and national political correspondent, is a freelance writer. 

Top Image: 1963 mugshot of Jack Ruby (Credit: Dallas Police Department photographic records via PICRYL)

One thought on “Jack Ruby: The Many Faces of Oswald’s Assasin

  1. Jordan Rapport says:

    My grandparents lived around the corner from Jack Ruby’s mother’s house. My family knew Jack ruby and had to testify in the Warren commission.

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