JACK RUBY: WHY Did He Kill Oswald?

Jack Ruby’s name has been seared into history for a single, shocking act: killing Lee Harvey Oswald on live television, just days after President John F. Kennedy’s assassination. For decades, speculation and myth have swirled around this infamous figure. Was he a mafia hitman, a deluded loner, or something more complex? As it turns out, the truth about Jack Ruby resists any neat label—and understanding him forces us to confront the tangles of identity, politics, and personal turmoil swirling through the America of the early 1960s.

Who Was Jack Ruby, Really?

Jack Ruby wasn’t, as some might picture, a hardened underworld figure lurking in the shadows. Instead, Ruby was, in many ways, a product of his time—a hustler, nightclub owner, minor showman, and a man profoundly conscious of his identity as an American Jew. He navigated a difficult social undercurrent in Dallas, a city straddling the progressive ideals of the North and the entrenched segregation of the South. This duality left Dallas's Jewish community, including Ruby, caught between competing pressures during the era’s heated civil rights struggles.

Yet, Ruby’s Jewishness wasn’t simply a footnote in his story—it was central to how he saw himself and his place in the world. He was an active member of a prominent Dallas synagogue and acutely aware of rising antisemitism. The period running up to Kennedy’s ill-fated visit coincided with an outbreak of antisemitic sentiment, stoking fears that any major event—especially something as traumatic as the president’s assassination—might be blamed on the Jewish community. Ruby’s sensitivity to these issues colored much of his behavior.

A Man Drawn to the Spotlight

Unlike the cold calculation of a professional assassin, Ruby’s actions before and after Oswald’s shooting were chaotic and impulsive. He made himself highly visible around Dallas in the days leading up to the murder, crossing paths with police and the press alike. Rather than hiding in the shadows, he acted like a man desperate to be in the middle of the action, offering advice, orchestrating moments with key officials, and showing up on television. His deep need for attention mirrored the way he ran his clubs—often as his own bouncer, MC, and would-be comedian. It almost seems as if, in those frenzied days, he found himself as the star of his own tragic show.

The Critical Day: Chaos, Coincidence, or Conspiracy?

Ruby’s involvement in Oswald’s murder on November 24, 1963, has spawned endless theories. Some insist he was a mob hitman sent to silence Oswald; others see a confused individual overtaken by emotion and circumstance. On that fateful day, Ruby’s movements were thoroughly unsuspicious for those who knew him. He was seen around Dallas tending to nightclub business—sending money to a needy dancer via Western Union, inadvertently stumbling upon the police station commotion just as Oswald was being transferred. In his later accounts, Ruby described entering a “fugue state” before shooting Oswald, suggesting an act less of premeditation and more of overwhelming impulse.

Was Ruby’s presence at the police station mere coincidence, or was it part of a deeper plot? Despite multiple interviews and even access to personal notes taken by his rabbi—who visited Ruby every other day in prison—the true motive remains opaque. Ruby himself offered numerous, often conflicting explanations, fueling both suspicion and sympathy.

A Man of Contradictions

After the killing, Ruby’s mental state grew increasingly unstable. He gave shifting accounts to anyone who would listen, from journalists to his family and legal team. Erotic trial, media scrutiny, and wild speculation seemed to amplify his confusion. Legendary journalists like Dorothy Kilgallen sought answers from Ruby, convinced he held the key to unlocking the Kennedy assassination’s mysteries. Yet whatever truths he may have held were tangled in a shifting narrative that changed by the day. Was this confusion the product of a guilty conscience, mental illness, or both?

Ruby’s mental health became a central issue during his high-profile trial. Despite being banned from testifying on his own behalf, Ruby regularly held impromptu press conferences from jail, relishing the spotlight. His erratic behavior, paranoia, and delusions—he believed he’d started a second Holocaust—led many to question his sanity. Was he feigning madness, or was he truly overwhelmed by the tragedy and chaos surrounding him? The answer, like so much about Jack Ruby, remains maddeningly elusive.

Legacy of a Mystery

It’s tempting to view Ruby as nothing more than a narrative device within the grander Kennedy assassination story—a convenient villain, a possible conspirator, or a tragic scapegoat. But Ruby was also a deeply human character, shaped by his community, circumstances, and personal frailties. He represented a certain kind of mid-century American striver, constantly seeking recognition and a place in the spotlight—yet forever out of step, unable to control or command the stage he so desperately wanted.

In the end, Jack Ruby’s story is one of contradiction and chaos. He was both insider and outsider, a person driven by identity and insecurity, performance and paranoia. He leaves us with more questions than answers—an enigma at the center of one of the most debated moments in American history.

Taking the Story Further

The fascination with Jack Ruby will likely never fade. As Danny Fingeroth, author of “Jack Ruby, the Many Faces of Oswald’s Assassin,” points out, the truth of who Jack Ruby was may never be fully unraveled. Yet, his bizarre journey from low-level showman to infamous assassin offers a unique window into the anxieties, divisions, and dark fascinations of 20th-century America.

If you’re eager to explore further, you can find Fingeroth’s book through bookstores and online, and dig deeper into the testimonies from those who knew Ruby—his family, his rabbi, his friends, and contemporaries from the world of Dallas nightlife.

The story of Jack Ruby reminds us that history is rarely as clear-cut as we might wish. Sometimes, the people at the heart of the mystery are themselves mysteries—and understanding them requires us to face the ambiguities of human nature itself.

If you’re interested in stories that lie at the intersection of the visible and invisible, consider subscribing and following along as more of these mysteries are explored.