Jack Ruby: Mobster, Intelligence Agent, or Small-time Hustler?

Marina McGowan

Professor Jeffrey Bass was not born at the time of the John F. Kennedy assassination, but as a scholar of political history with a specialization in the United States presidency, this subject has sparked more than a passing interest for him.

Bass shared some of his opinions and evidence based on his experience as a historian who has studied a variety of notable conspiracy theories in U.S. history. In dealing with certain aspects of the assassination, he focuses on Jack Ruby, the owner of a Dallas, Texas nightclub and admirer of President Kennedy.

There have been many explanations concerning the enigma surrounding Jack Rubenstein, better known as Jack Ruby, but no one is for sure who he really was, what his true motive for killing Lee Harvey Oswald was and how he knew the specific time when the Dallas Police Department was going to be transporting Oswald from the jail.

On November 24, 1963, Dallas police were transferring Oswald, who had been arrested for assassinating President John F. Kennedy two days earlier, from one jail to another. A crowd of journalists, photographers and police crowded around in the jail’s basement garage, and watched as Oswald was led out and was about to be placed in a police car.

Oswald did not make it very far as Ruby stepped forward, drew a gun and killed him. The whole incident was captured on videotape and played back on television, as shocking viewers witnessed the crime.

Ruby was found guilty of Oswald’s murder on March 14, 1964, and sentenced to death. He appealed and won a retrial on the basis that procedural errors had occurred during the trial. At an appeal hearing on September 9, 1965, in Dallas, Ruby passed this note to his attorney, Elmer Gertz: “Elmer, you must believe me, that I am not imagining crazy thoughts, etc. This is all so hopeless, that they have everything in the bag and there isn’t any chance of hope for me. These hearings are just stalling for time.”

The note shows Ruby’s declining mental state. In 1967, Ruby died of cancer in prison before a new trial could be held.

After Kennedy was killed, Vice President Lyndon Johnson became President, and he appointed the President’s Commission on the Assassination of President Kennedy. Chaired by Supreme Court Chief Justice Earl Warren, the Commission investigated circumstances surrounding the shootings of Kennedy and Oswald. In September 1964, the Commission reported it had found no evidence that Oswald and Ruby were involved in a conspiracy to assassinate the president.

However, Bass has other inclinations, with most of his impressions coming from the work of David Belin, who was legal counsel for the Warren Commission in its investigation of the circumstances surrounding the Kennedy assassination.

Ruby’s rabbi, Hillel Silverman, had the opportunity to interview him in prison numerous times after the shooting of Oswald. Ruby apparently claimed that he had not expected to cross paths with Oswald on the morning of November 24 when the shooting took place, Bass said. Ruby was no stranger to the Dallas Police Department. Between 1949 and November 24, 1963, he was arrested eight times on various charges, ranging from disturbing the peace to selling liquor after hours.

“Ruby asserted that, through his association with members of the Dallas police department, he had been able to attend the press conference two days before where Oswald was interviewed about his purported role in the murders of JFK and police officer J.D. Tippit,” Bass said. “Ruby claims to have had a gun in his pocket on November 22 and could have shot Oswald on that earlier occasion.”

So why did the murder occur on November 24 instead when apparently Ruby was unaware that he would run into Oswald? asks Bass.

Rabbi Silverman reported that Ruby was moved by news reports that Jackie Kennedy, John’s widow, might have to return to Dallas to testify in Oswald’s trial. David Belin wanted to submit Ruby to a lie detector test to verify if this was truly the reason for killing Oswald. Supreme Court Chief Justice Earl Warren rejected the use of a polygraph on the grounds of its dependability. But Ruby insisted on a lie detector test, despite the advice of his lawyers, and was given the opportunity in July 1964.

As administered by an FBI agent who authenticated the results, Ruby claimed not to have known Oswald before the JFK shooting, not to have assisted Oswald in the shooting, not to have acted on anyone’s orders in killing Oswald, not to have killed Oswald in order to silence him, to have testified honestly before the Warren Commission and to have killed Oswald to spare Jackie Kennedy a trial appearance.

“It is true that individuals can be trained to “beat” a lie detector test, though such instances are rare,” Bass said. “It is also unlikely that if Ruby was involved in a conspiracy, that he would have insisted upon taking a polygraph test. The risks of exposure entailed were considerable.”

Bass said that Belin highlighted another circumstance. A U.S. postal inspector named Harry Holmes just happened by chance to skip church on Sunday morning on November 24 and head down to the Dallas police station to see if he could help his friend, Captain Will Fritz, of the homicide division.

Upon seeing Holmes, Fritz offered him the chance to interview Oswald because Oswald had used a money order to buy the rifle that had killed the President.

“The time added onto the interview by virtue of Holmes being there amounted to more than half an hour, which ultimately put Ruby and Oswald in the same location for the fateful shooting,” Bass said. “So now Holmes and/or Fritz would have to be in on the conspiracy as well. The more players that are allegedly involved in such a cover-up, the more dubious such an explanation becomes.”

To recap the Ruby angle of the assassination, Bass said that Ruby also wired some money to a nightclub employee of his just four minutes before the shooting of Oswald. There is no evidence that he had any idea on November 24 that he would run into his ultimate target.

“Being a half block away just four minutes beforehand is cutting things awfully close for such an important mission if he was truly part of a conspiracy,” Bass said. “Friday, November 22 seems to have been the better time for Ruby to kill Oswald if that was always his plan and there is no evidence that Ruby knew that another opportunity would materialize on November 24.”

Much has been made of Ruby’s Mafia connections. But if the Mafia ordered the hit on Oswald, it makes no sense that they would have it conducted in such a way that the hit man [Ruby] was almost certainly going to be captured by police and thus potentially interrogated to the point of revealing the entire plan.

“Since David Belin’s conclusions are largely based on interviewing Rabbi Silverman, we might also consider the credibility of a man of the cloth,” Bass said. “Of course anyone can potentially be lying, but there is no apparent indication of why Silverman would do so.”

Turning to the Warren Commission, on a superficial level this body has fostered suspicions because their witnesses testified privately and the public has not yet had access to all of the discoveries that it made.

“Add to that the burial of John F. Kennedy’s body at sea, the Zapruder film which has been interpreted in a variety of ways, Ruby’s alleged Mafia connections, Oswald’s sympathy with Communism and CIA assassination plots against Fidel Castro in the early 1960s, and you have much grist for the conspiracy theorist’s mill,” Bass said.

Americans have long been fascinated with the conspiracy as a way to apply a pattern to complex and overwhelming events. The outbreak of the American War for Independence and Civil War were to some extent attributable to conspiracy theories on both sides.

“There are those who believe that FDR knew of the Pearl Harbor attack beforehand and kept America’s guard down to give himself a clear rationale for entering World War II,” Bass said. “More recently there have been some dubious claims that members of the Bush administration either planned or knew beforehand of the September 11, 2001 attacks. These fanciful explanations do not hold well to scrutiny and common sense. Any conspiracy involving government organizations assumes far better communication within our vast federal bureaucracy that evidence suggests has ever existed.”

The more individuals who would have to be in on such an enterprise, the less likely it is that a secret can be kept. As far as Ruby and his knowledge of the President’s route through Dallas is still unknown, however, Bass has one theory. “My problem with that possibility is that Ruby’s relationship with the Dallas Police Department was common knowledge and thus would lead an obvious trail back to him after his public slaying of Oswald,” Bass said. “From what I have read, there were logical reasons for selecting the Dallas Trade Mart as JFK’s ultimate destination that day instead of other possible sites.”