|Intro||American nightclub operator who killed American presidential assassin Lee Harvey Oswald|
|A.K.A.||Jack Leon Ruby, Jacob Leon Rubenstein|
|From||United States of America|
|Birth||25 March 1911, Chicago, USA|
|Death||3 January 1967, Dallas, USA (aged 55 years)|
Jack Leon Ruby (born Jacob Leon Rubenstein; April 25, 1911 – January 3, 1967) was a Dallas, Texas nightclub owner. He fatally shot Lee Harvey Oswald on November 24, 1963, while Oswald was in police custody after being charged with assassinating United States President John F. Kennedy and murdering Dallas policeman J. D. Tippit about an hour later. A Dallas jury found him guilty of murdering Oswald, and he was sentenced to death. Ruby's conviction was later appealed, and he was granted a new trial. However, as the date for his new trial was being set, Ruby became ill in prison and died of a pulmonary embolism from lung cancer on January 3, 1967.
In September 1964, the Warren Commission concluded that Ruby acted alone in killing Oswald. Various groups believed Ruby was involved with major figures in organized crime and that he killed Oswald as part of an overall plot surrounding the assassination of Kennedy.
Childhood and early life
Jack Ruby was born Jacob Leon Rubenstein, on March 25, 1911, in the Maxwell Street area of Chicago the son of Joseph Rubenstein and Fannie Turek Rutkowski (or Rokowsky), both Polish-born Orthodox Jews from Sokołów. Ruby was the fifth of his parents' 10 surviving children. While he was growing up, his parents were often violent towards each other and regularly separated; Ruby's mother was eventually committed to a mental hospital. His troubled childhood and adolescence was marked by juvenile delinquency with time being spent in foster homes. At age 11 in 1922, he was arrested for truancy. Ruby eventually skipped school enough times that he spent time at the Institute for Juvenile Research. Still a young man, he sold horse-racing tip sheets and various novelties, then acted as a business agent for a local refuse collectors union that later became part of the International Brotherhood of Teamsters (IBT).
From his early childhood, Ruby was nicknamed "Sparky" by those who knew him. His sister, Eva Grant, said that he acquired the nickname because he resembled a slow-moving horse named "Spark Plug" or "Sparky" in the contemporary comic strip Barney Google. ("Spark Plug" debuted as a character in the strip in 1922, when Ruby was 11.) Other accounts say that the name was given because of his quick temper. In either event, Grant stated that Ruby did not like the nickname Sparky, and was quick to fight anyone who called him that.
In the 1940s, Ruby frequented race tracks in Illinois and California. He was drafted in 1943 and served in the U.S. Army Air Forces during World War II, working as an aircraft mechanic at U.S. bases until 1946. He had an honorable record and was promoted to Private First Class. Upon discharge, in 1946, Ruby returned to Chicago.
In 1947, Ruby moved to Dallas where he and his brothers soon afterward shortened their surnames from Rubenstein to Ruby. The stated reason for this was that the name "Rubenstein" was too long and that he was "well known" as Jack Ruby. Ruby later went on to manage various nightclubs, strip clubs, and dance halls. He developed close ties to many Dallas Police officers who frequented his nightclubs, where he provided them with free liquor, prostitutes and other favors.
Ruby never married and had no children.
Illegal activities in Dallas
There was evidence indicating Jack Ruby had been involved in the underworld activities of illegal gambling, narcotics, and prostitution.
A 1956 FBI report stated that their informant, Eileen Curry, reported that in January of that year, she moved to Dallas with her boyfriend, James Breen, after jumping bond on narcotics charges. Breen told her that he had made connections with a large narcotics setup operating between Texas, Mexico, and the East, and that "in some fashion, James got the okay to operate through Jack Ruby of Dallas."
Former Dallas County Sheriff Steve Guthrie told the FBI that he believed Ruby "operated some prostitution activities and other vices in his club" since living in Dallas.
Dallas disc jockey Kenneth Dowe testified that Ruby was known around the station for "procuring women for different people who came to town."
John F. Kennedy assassination
The Warren Commission attempted to reconstruct Ruby's movements from November 21, 1963 through November 24. The Commission reported that he was attending to his duties as the proprietor of the Carousel Club located at 1312 1/2 Commerce St. in downtown Dallas and the Vegas Club in the city's Oak Lawn district from the afternoon of November 21 to the early hours of November 22.
November 22: The assassination of Kennedy
According to the Warren Commission, Ruby was in the second-floor advertising offices of the Dallas Morning News, five blocks away from the Texas School Book Depository, placing weekly advertisements for his nightclubs when he learned of the assassination around 12:45 p.m. Ruby then made phone calls to his assistant at the Carousel Club and to his sister. The Commission stated that an employee of the Dallas Morning News estimated that Ruby left the newspaper's offices at 1:30 p.m., but indicated that other testimony suggested he may have left earlier.
According to the Warren Commission, Ruby arrived back at the Carousel Club shortly before 1:45 p.m. to notify employees that the club would be closed that evening.
Ruby was seen in the halls of the Dallas Police Headquarters on several occasions after Lee Harvey Oswald's arrest on November 22, 1963. Newsreel footage from WFAA-TV (Dallas) and NBC shows that Ruby impersonated a newspaper reporter during a press conference at Dallas Police Headquarters on the night of Kennedy's death. District Attorney Henry Wade briefed reporters at the press conference telling them that Lee Oswald was a member of the anti-Castro Free Cuba Committee. Ruby was one of several people there who spoke up to correct Wade, saying, "Henry, that's the Fair Play for Cuba Committee," a pro-Castro organization. One month after his arrest for killing Oswald, Ruby told the FBI that he had his loaded snub-nosed Colt Cobra .38 revolver in his right pocket during the press conference.
November 24: The killing of Oswald
On November 24, Ruby drove into town with his pet dachshund Sheba (whom he would often jokingly refer to as his "wife") to send an emergency money order at the Western Union on Main Street to one of his employees. The time stamp of completion for the cash transaction on the money order was 11:17 a.m. Ruby then walked one half block to the nearby Dallas police headquarters, where he made his way into the basement via either the Main Street ramp or a stairway accessible from an alleyway next to the Dallas Municipal Building. At 11:21 a.m. CST—while authorities were escorting Oswald through the police basement to an armored car that was to take him to the nearby county jail—Ruby stepped out from a crowd of reporters with his .38 Colt Cobra revolver aimed at Oswald's abdomen and fired a single round at point blank range, mortally wounding him. The bullet entered Oswald's left side in the front part of the abdomen and caused damage to his spleen, stomach, aorta, vena cava, kidney, liver, diaphragm, and eleventh rib before coming to rest on his right side. Oswald made a cry of anguish and his manacled hands clutched at his abdomen as he writhed with pain, and he slumped to the concrete paving, where he moaned several times. Police detective Billy Combest suddenly recognized Ruby and exclaimed: "Jack, you son of a bitch!" Ruby was immediately subdued by agents and police. A moaning Oswald was carried back into the basement level jail office. He lost consciousness shortly thereafter. Taken by ambulance to Parkland Memorial Hospital—the same hospital where President Kennedy was pronounced dead two days earlier, Oswald died at 1:07 p.m.
The crowd outside the headquarters burst into applause when they heard that Oswald had been shot.
A network television pool camera was broadcasting live to cover the transfer; millions of people watching on NBC witnessed the shooting as it happened and on other networks within minutes afterward. Several photographs were taken of the event just before, as, and after Ruby pulled the trigger. In 1964, Robert H. Jackson of the Dallas Times Herald was awarded the Pulitzer Prize for Photography for his image of the shooting of Lee Harvey Oswald by Jack Ruby.
After his arrest, Ruby asked Dallas attorney Tom Howard to represent him. Howard accepted and asked Ruby if he could think of anything that might damage his defense. Ruby responded that there would be a problem if a man by the name of "Davis" should come up. Ruby told his attorney that he "... had been involved with Davis, who was a gunrunner entangled in anti-Castro efforts".
Later, Ruby replaced attorney Tom Howard with prominent San Francisco defense attorney Melvin Belli, who agreed to represent Ruby pro bono. On March 14, 1964, Ruby was convicted of murder with malice and was sentenced to death.
Ruby's conviction was overturned by the Texas Court of Criminal Appeals on the grounds that "an oral confession of premeditation made while in police custody" should have been ruled inadmissible, because it violated a Texas criminal statute. The court also ruled that the venue should have been changed to a Texas county other than the one in which the high-profile crime had been committed. Ruby died technically unconvicted, because his original conviction was overturned and his retrial was pending at the time of his death.
During the six months following Kennedy's assassination, Ruby repeatedly asked, orally and in writing, to speak to the members of the Warren Commission. The commission initially showed no interest. Only after Ruby's sister Eileen wrote letters to the commission (and her letters became public) did the Warren Commission agree to talk to Ruby. In June 1964, Chief Justice Earl Warren, then-Representative Gerald R. Ford of Michigan, and other commission members went to Dallas to see Ruby. Ruby asked Warren several times to take him to Washington D.C., saying "my life is in danger here" and that he wanted an opportunity to make additional statements. He added: "I want to tell the truth, and I can't tell it here." Warren told Ruby that he would be unable to comply, because many legal barriers would need to be overcome, and public interest in the situation would be too heavy. Warren also told Ruby that the commission would have no way of protecting him, since it had no police powers. Ruby said he wanted to convince President Lyndon Johnson that he was not part of any conspiracy to kill Kennedy.
Eventually, the appellate court agreed with Ruby's lawyers that he should be granted a new trial. On October 5, 1966, the court ruled that his motion for a change of venue before the original trial court should have been granted. Ruby's conviction and death sentence were overturned. Arrangements were underway for a new trial to be held in February 1967 in Wichita Falls, Texas, when on December 9, 1966, Ruby was admitted to Parkland Hospital in Dallas, suffering from pneumonia. A day later, doctors realized he had cancer in his liver, lungs, and brain. Three weeks later, he died.
Ruby died of a pulmonary embolism, secondary to bronchogenic carcinoma, on January 3, 1967, at Parkland Hospital, the same facility where Oswald had died and where President Kennedy had been pronounced dead after his assassination. He was buried beside his parents in the Westlawn Cemetery in Norridge, Illinois.
The Warren Commission found no evidence linking Ruby's killing of Oswald with any broader conspiracy to assassinate Kennedy. In 1964, the Warren Commission provided a detailed biography of Ruby's life and activities to help ascertain whether he was involved in a conspiracy to assassinate Kennedy. The Commission indicated that there was not a "significant link between Ruby and organized crime" and said he acted independently in killing Oswald.
Warren Commission investigator David Belin said that postal inspector Harry Holmes arrived unannounced at the Dallas police station and, upon invitation by the investigators, questioned Oswald, thus delaying his transfer by half an hour. Belin concluded that, had Ruby been part of a conspiracy, he would have been downtown 30 minutes earlier.
In Gerald Posner's book Case Closed: Lee Harvey Oswald and the Assassination of JFK, Ruby's friends, relatives and associates claimed that he was upset over President Kennedy's death, even crying on occasions and closing his clubs for three days as a mark of respect. They also disputed the conspiracy claims, saying that Ruby's connection with gangsters was minimal at most and that he was not the sort to be entrusted with such an act within a high-level conspiracy.
Dallas reporter Tony Zoppi, who knew Ruby well, claimed that one "would have to be crazy" to entrust Ruby with anything as important as a high-level plot to kill Kennedy since he "couldn't keep a secret for five minutes ... Jack was one of the most talkative guys you would ever meet. He'd be the worst fellow in the world to be part of a conspiracy, because he just plain talked too much." He and others described Ruby as the sort who enjoyed being at "the center of attention", trying to make friends with people and being more of a nuisance.
Some writers, including former Los Angeles District Attorney Vincent Bugliosi, dismiss Ruby's connections to organized crime as being highly minimal: "It is very noteworthy that without exception, not one of these conspiracy theorists knew or had ever met Jack Ruby. Without our even resorting to his family and roommate, all of whom think the suggestion of Ruby being connected to the mob is ridiculous, those who knew him, unanimously and without exception, think the notion of his being connected to the Mafia, and then killing Oswald for them, is nothing short of laughable."
Bill Alexander, who prosecuted Ruby for Oswald's murder, equally rejected any suggestions that Ruby was part-and-parcel of organized crime, claiming that conspiracy theorists based it on the claim that "A knew B, and Ruby knew B back in 1950, so he must have known A, and that must be the link to the conspiracy."
Ruby's brother Earl denied allegations that Jack was involved in racketeering Chicago nightclubs, and author Gerald Posner suggested that witnesses may have confused Ruby with Harry Rubenstein, a convicted Chicago felon. Entertainment reporter Tony Zoppi was also dismissive of mob ties. He knew Ruby and described him as a "born loser".
Author Norman Mailer and others have questioned why Ruby would have left his two beloved dogs in his car if he had planned on killing Oswald at police headquarters.
Other investigations and dissenting theories
Some critics have not accepted the conclusions of the Warren Commission and have proposed several other theories.
Ruby was arrested immediately after shooting Oswald, and he told several witnesses that he had been distraught over President Kennedy's death and had helped the city of Dallas "redeem" itself in the eyes of the public, and that his motive for killing Oswald was "saving Mrs. Kennedy the discomfiture of coming back to trial". He also claimed he shot Oswald on the spur of the moment when the opportunity presented itself, without considering any reason for doing so. Ruby told the FBI he was "in mourning" Friday and Saturday. He said he cried when he heard the President was shot, "cried a great deal" Saturday afternoon and was depressed Saturday night. He explained that this grief was caused by his great love for the President and his sympathy for the Kennedy family. The anguish over the assassination, Ruby stated, finally "reached the point of insanity", suddenly compelling him to shoot when Oswald walked to the police ramp that Sunday morning. At the time of the shooting, Ruby said he was taking phenmetrazine, a central nervous system stimulant. Ruby broke into tears at his bond hearing in January 1964, as he talked to reporters regarding the assassination of President Kennedy. His voice breaking, Ruby said that he could not understand "how a great man like that could be lost". According to an unnamed Associated Press source, Ruby made a final statement from his hospital bed on December 19, 1966, that he alone had been responsible for the murder of Lee Harvey Oswald. "There is nothing to hide ... There was no one else," Ruby said.
White House correspondent Seth Kantor, who was a passenger in President Kennedy's motorcade, testified that after President Kennedy was shot, he had visited Parkland Hospital while doctors were trying to save the President's life. Kantor said that as he entered the hospital, at about 1:30 p.m., he felt a tug on his coat. He turned around to see Jack Ruby, who called him by his first name and shook his hand; he said that he had become acquainted with Ruby while he was a reporter for the Dallas Times Herald newspaper. According to Kantor, Ruby asked him if he thought that it would be a good idea for him to close his nightclubs for the next three nights because of the tragedy and Kantor responded with thinking that doing so would be a good idea.
The Warren Commission dismissed Kantor's testimony, saying that the encounter at Parkland Hospital would have had to take place in a span of a few minutes before and after 1:30 pm, as evidenced by telephone company records of calls made by both people then. The Commission also pointed to contradictory witness testimony and to the lack of video confirmation of Ruby at the scene. The Commission concluded that "Kantor probably did not see Ruby at Parkland Hospital" and "may have been mistaken about both the time and the place that he saw Ruby".
In 1979, the House Select Committee on Assassinations reexamined Kantor's testimony and stated, "While the Warren Commission concluded that Kantor was mistaken [about his Parkland encounter with Ruby], the Committee determined he probably was not."
Kantor also reported that Ruby might have tampered with evidence while at Parkland. Goaded by the Warren Commission's dismissal of his testimony, Kantor researched the Ruby case for years. In a later published book Who Was Jack Ruby?, Kantor wrote:
The mob was Ruby's "friend." And Ruby could well have been paying off an IOU the day he was used to kill Lee Harvey Oswald. Remember: "I have been used for a purpose," the way Ruby expressed it to Chief Justice Warren in their June 7, 1964 session. It would not have been hard for the mob to maneuver Ruby through the ranks of a few negotiable police [to kill Oswald].
The House Select Committee on Assassinations, in its 1979 Final Report, opined:
... Ruby's shooting of Oswald was not a spontaneous act, in that it involved at least some premeditation. Similarly, the committee believed it was less likely that Ruby entered the police basement without assistance, even though the assistance may have been provided with no knowledge of Ruby's intentions ... The committee was troubled by the apparently unlocked doors along the stairway route and the removal of security guards from the area of the garage nearest the stairway shortly before the shooting ... There is also evidence that the Dallas Police Department withheld relevant information from the Warren Commission concerning Ruby's entry to the scene of the Oswald transfer.
According to Lieutenant Billy Grammer, a dispatcher for the Dallas Police Department, he received an anonymous phone call at 3 a.m. on November 24 from a man who knew Grammer's name. The caller told Grammer that he knew of the plan to move Oswald from the basement and that unless the plans for Oswald's transfer were changed, the caller warned "we are going to kill him". After Oswald was shot, Grammer, who knew Ruby, and found the voice familiar at the time of the call, identified Ruby as the caller. Grammer remained convinced that Ruby's shooting of Oswald was "a planned event".
Detective Archer testified to the Warren Commission that when he searched Jack Ruby after his arrest, he was worried about Oswald's condition and he said to Ruby, "Jack, I think you killed him." Archer said that Ruby looked him straight in the eye and said, "Well, I intended to shoot him three times." Seth Kantor believes that Ruby's response to Archer does not suggest a spontaneous reaction, and the very word "intended" implies having prior intention.
Ruby's explanation for killing Oswald would be "exposed ... as a fabricated legal ploy", according to the House Select Committee on Assassinations. In a private note to one of his attorneys, Joseph Tonahill, Ruby wrote: "Joe, you should know this. My first lawyer Tom Howard told me to say that I shot Oswald so that Caroline and Mrs. Kennedy wouldn't have to come to Dallas to testify. OK?"
G. Robert Blakey, chief counsel for the House Select Committee on Assassinations from 1977 to 1979, said: "The most plausible explanation for the murder of Oswald by Jack Ruby was that Ruby had stalked him on behalf of organized crime, trying to reach him on at least three occasions in the forty-eight hours before he silenced him forever."
In his testimony before the Warren Commission, Russell Lee Moore Knight said that Ruby held no bitterness towards Oswald and called him "a good looking guy" who resembled Paul Newman.
In his book Contract on America, David Scheim noted that although some people claimed that they saw Ruby upset over the weekend of the assassination, others said that he was not. On Friday night, TV newsman Vic Robertson Jr. saw Ruby at police headquarters and reported that Ruby "appeared to be anything but under stress or strain. He seemed happy, jovial, was joking and laughing". Announcer Glen Duncan also testified that Ruby "was not grieving" and if anything, was "happy that evidence was piling up against Oswald".
Scheim also presented evidence that he claimed showed that Ruby made a "candid confession" when giving testimony to the Warren Commission. During his testimony, Ruby teared up when talking about a Saturday morning eulogy for President Kennedy, but after composing himself, inexplicably said, "I must be a great actor, I tell you that." Ruby also remarked that "they didn't ask me another question: "If I loved the President so much, why wasn't I at the parade?"" (referring to the presidential motorcade) and "it's strange that perhaps I didn't vote for President Kennedy, or didn't vote at all, that I should build up such a great affection for him".
Jada, a stripper at Ruby's club, in an interview with ABC's Paul Good: "I believe he disliked Bobby Kennedy".
Schiem also noted several people who knew Ruby, who claimed that the patriotic statements Ruby professed were quite out of character. Harry Hall, Ruby's partner in a gambling operation, told the FBI that "Ruby was the type who was interested in any way to make money" and also said that he "could not conceive of Ruby doing anything out of patriotism". Jack Kelly, who had known Ruby casually since 1943, "scoffed at the idea of a patriotic motive being involved by Ruby in the slaying of Oswald", and reportedly stated that he "could not see Ruby" killing Oswald "out of patriotism" but "for publicity or ... for money".
Ruby's friend Paul Roland Jones was paraphrased by his FBI interviewers as affirming that:
from his acquaintance with Ruby he doubted that he would have become emotionally upset and killed Oswald on the spur of the moment. He felt Ruby would have done it for money.
Following Ruby's March 1964 conviction for murder with malice, Ruby's lawyers, led by Sam Houston Clinton, appealed to the Texas Court of Criminal Appeals, the highest criminal court in Texas. Ruby's lawyers argued that he could not have received a fair trial in Dallas because of the excessive publicity surrounding the case. A year after his conviction, in March 1965, Ruby conducted a brief televised news conference in which he stated: "Everything pertaining to what's happening has never come to the surface. The world will never know the true facts of what occurred, my motives. The people who had so much to gain, and had such an ulterior motive for putting me in the position I'm in, will never let the true facts come above board to the world." When asked by a reporter, "Are these people in very high positions, Jack?", he responded "Yes."
Journalist Seth Kantor speculated in 1978 that the man by the name of "Davis" that Ruby mentioned may have been Thomas Eli Davis III, a CIA-connected mercenary.
Dallas Deputy Sheriff Al Maddox claimed: "Ruby told me, he said, 'Well, they injected me for a cold.' He said it was cancer cells. That's what he told me, Ruby did. I said you don't believe that bullshit. He said, 'I damn sure do!' [Then] one day when I started to leave, Ruby shook hands with me and I could feel a piece of paper in his palm ... [In this note] he said it was a conspiracy and he said ... if you will keep your eyes open and your mouth shut, you're gonna learn a lot. And that was the last letter I ever got from him." In the note, Ruby claimed he was part of a conspiracy, and that his role was to silence Oswald. Not long before Ruby died, according to an article in the London Sunday Times, he told psychiatrist Werner Teuter that the assassination was "an act of overthrowing the government" and that he knew "who had President Kennedy killed". He added: "I am doomed. I do not want to die. But I am not insane. I was framed to kill Oswald."
In his book, Contract on America, David Scheim presented evidence that Mafia leaders Carlos Marcello and Santo Trafficante, Jr., as well as organized labor leader Jimmy Hoffa, ordered the assassination of President Kennedy. Scheim cited in particular a 25-fold increase in the number of out-of-state telephone calls from Jack Ruby to associates of these crime bosses in the months before the assassination. According to author Vincent Bugliosi, both the Warren Commission and the House Select Committee on Assassinations determined all of these calls were related to Ruby seeking help from the American Guild of Variety Artists in a matter concerning two of his competitors. The House Select Committee on Assassinations report stated "... that most of Ruby's phone calls during late 1963 were related to his labor troubles. In the light of the identity of some of the individuals with whom Ruby spoke, however, the possibility of other matters being discussed could not be dismissed."
In his memoir, Bound by Honor, Bill Bonanno, son of New York Mafia boss Joseph Bonanno, stated that he realized that certain Mafia families were involved in the JFK assassination when Ruby killed Oswald, since Bonanno was aware that Ruby was an associate of Chicago mobster Sam Giancana.
Associations with organized crime and gunrunning allegations
In 1979, fifteen years after the Warren report, the House Select Committee on Assassinations undertook a similar investigation of Ruby and said that he "had a significant number of associations and direct and indirect contacts with underworld figures" and "the Dallas criminal element" but that he was not a "member" of organized crime.
Ruby was known to have been acquainted with both the police and the Mafia. The HSCA said that Ruby had known Chicago mobster Sam Giancana (1908–1975) and Joseph Campisi (1918–1990) since 1947, and had been seen with them on many occasions. After an investigation of Joe Campisi, the HSCA found:
While Campisi's technical characterization in federal law enforcement records as an organized crime member has ranged from definite to suspected to negative, it is clear that he was an associate or friend of many Dallas-based organized crime members, particularly Joseph Civello, during the time he was the head of the Dallas organization. There was no indication that Campisi had engaged in any specific organized crime-related activities.
Similarly, a PBS Frontline investigation into the connections between Ruby and Dallas organized crime figures reported the following:
In 1963, Sam and Joe Campisi were leading figures in the Dallas underworld. Jack knew the Campisis and had been seen with them on many occasions. The Campisis were lieutenants of Carlos Marcello, the Mafia boss who had reportedly talked of killing the President.
A day before Kennedy was assassinated, Ruby went to Joe Campisi's restaurant. At the time of the Kennedy assassination, Ruby was close enough to the Campisis to ask them to come see him after he was arrested for shooting Lee Oswald. Joe Campisi and his wife visited with Jack Ruby in jail for ten minutes on November 30, 1963.
Howard P. Willens—the third-highest official in the Department of Justice and assistant counsel to J. Lee Rankin—helped organize the Warren Commission. Willens also outlined the Commission's investigative priorities and terminated an investigation of Ruby's Cuban related activities. An FBI report states that Willens's father had been Tony Accardo's next door neighbor going back to 1958. In 1946, Tony Accardo allegedly asked Jack Ruby to go to Texas with Mafia associates Pat Manno and Romie Nappi to make sure that Dallas County Sheriff Steve Gutherie would acquiesce to the Mafia's expansion into Dallas.
Four years before the assassination of President Kennedy, Ruby went to see a man named Lewis McWillie in Cuba. Ruby considered McWillie, who had previously run illegal gambling establishments in Texas, to be one of his closest friends. At the time Ruby visited him, in August 1959, McWillie was supervising gambling activities at Havana's Tropicana Club. Ruby told the Warren Commission that his August trip to Cuba was merely a social visit at the invitation of McWillie. The House Select Committee on Assassinations would later conclude that Ruby "... most likely was serving as a courier for gambling interests". The committee also found "circumstantial," but not conclusive, evidence that "... Ruby met with [Mafia boss] Santo Trafficante in Cuba sometime in 1959."
James E. Beaird, who claimed to be a poker-playing friend of Jack Ruby, told both The Dallas Morning News and the FBI that Ruby smuggled guns and ammunition from Galveston Bay, Texas to Fidel Castro's guerrillas in Cuba in the late 1950s. Beaird said that Ruby "was in it for the money. It wouldn't matter which side, just [whichever] one that would pay him the most." Beaird said that the guns were stored in a two-story house near the waterfront, and that he saw Ruby and his associates load "many boxes of new guns, including automatic rifles and handguns" on a 50-foot military-surplus boat. He claimed that "each time that the boat left with guns and ammunition, Jack Ruby was on the boat."
Blaney Mack Johnson, an FBI informant, said Ruby was "active in arranging illegal flights of weapons from Miami" to pro-Castro forces in Cuba in the early 1950s.
In popular culture
Articles of clothing that Ruby wore when he killed Oswald—including his suit, hat and shoes—are on display at the Historic Auto Attractions museum in Roscoe, Illinois.
- Tom Skerritt's Fighting Back has footage of his shooting of Oswald in its opening credits news special on violence.
- In Oliver Stone's 1991 film JFK, Ruby was portrayed by actor Brian Doyle-Murray. Stone's perspective on events draws heavily from conspiracy theory researchers such as Jim Marrs and L. Fletcher Prouty. At least three scenes further detailing Ruby were removed from the film and are only available on DVD. One scene expanded on the Oswald shooting by showing corrupt Dallas police officers allowing Ruby to enter police headquarters through a restricted entrance.
- The 1992 film Ruby speculated on complex motivations that might have propelled Ruby into shooting Oswald. Among these were Ruby's reputation among family and friends as an assiduous, emotionally volatile publicity-seeker, and the influence of his long-time organized crime and Dallas police connections. Ruby was played by Danny Aiello.
- Ruby is one of the main characters of James Ellroy's novel The Cold Six Thousand. The plot revolves around the aftermath of the assassination of President Kennedy, and the assassinations of Senator Robert Kennedy and Martin Luther King, Jr. It speculates about government agencies like the CIA and the FBI, as well as figures like J. Edgar Hoover, and their links to Mafia and anti-Castro groups alleged to have been involved in the assassinations.
- In his 1989 novel Libra, Don DeLillo portrays Ruby as being part of a larger conspiracy surrounding the President's assassination, imagining that a mob member persuades Ruby to kill Oswald.
- In his autobiography, Robbie Robertson recounts a bizarre week when the Hawks' backing singer Ronnie Hawkins performed at the Skyline Lounge, a burnt-out club in Fort Worth, Texas. The owner, whom they knew as Jack, visited them at midnight and seemed to be constantly consuming "uppers". A few months later, after the assassination of President Kennedy, "the realisation settled in for all of us Hawks: Jack, the owner of the Skyline Lounge who seemed to be tweaked on pep pills was none other than Jack Ruby."
- The alternative rock band Camper Van Beethoven's 1989 album Key Lime Pie includes a song "Jack Ruby".
- Minnesota singer-songwriter Paul Metsa wrote the song "Jack Ruby" for his 1993 record Whistling Past the Graveyard.
- Ruby and Oswald (1978), a made-for-television movie, generally followed the official record as presented by the Warren Commission. Ruby was played by Michael Lerner.
- Ruby was also a character in one episode of the Starz TV series Magic City. He was portrayed by Holland Hayes in season two's third episode, "Adapt or Die". Ruby was sitting next to the main character, Ike Evans, on his way back from Cuba.
- Ruby is portrayed by Casey Siemaszko in the 2013 television drama Killing Kennedy.
- In the Hulu series 11.22.63, Jack Ruby is shown as a nightclub owner in 1960 Dallas played by Antoni Corone.
- In season 1 of the Godfather of Harlem he is mentioned.