Author: Carter McLellan – Date: January 2, 2025

Contents

1. Ruby’s early years
2. The Oswald Assassination
3. Ruby connections
4. Notes

[This article in incomplete and will be expanded in the future]

Ruby’s early years

Jack Leon Rubenstein was born around March 25, 1911, in Maxwell Street, Chicago, Illinois. His parents, Joseph Rubenstein and Fannie Turek Rutkowski were both Polish-born Orthodox Jews. Jack was fifth of their 10 surviving children. His parents were often violent toward each other and separated multiple times.

He was said to have had a troubled youth, often skipping school and spending time in foster homes. In 1922, at the age of 11, Jack was arrested for truancy, something that eventually led to time at the Institute for Juvenile Research. As a young man, Jack 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. He acquired the nickname “Sparky”, either from the comic Barney Google or his quick temper. He was supposed to have hated the name.

In the 1940s, while in his thirties, Jack frequented the race tracks in Illinois and California. But in 1943, he was drafted and served in the US Army Air Forces during WWII, working as an aircraft mechanic at US bases until 1946. He had an honorable record and was promoted to Private First Class. He returned to Chicago after his discharge in 1946.

Dallas

In 1947, Jack, 36, moved to Dallas, Texas, purportedly because of the failure of merchandise deals in Chicago and to help operate his sister’s, Eva Grant, nightclub. Others have speculated that Ruby came to Dallas as part of a Chicago mob move into the lucrative Dallas racket. Soon afterward he and his brothers shortened their surnames from Rubenstein to Ruby. The reason was supposed to be that the name “Rubenstein” was too long and that he was “well known” as Jack Ruby. Ruby would go on to manage various nightclubs, strip clubs, and dance halls in Dallas. He developed close ties to many Dallas police officers who frequented his nightclubs, where he treated them with free liquor, prostitutes and other favors. Ruby developed a reputation as of pay-off man of the Dallas police and as the man who had the fix with the Dallas County authorities, according to alleged Dallas FBI quotes from the Dallas underworld.

In 1952, Ruby reportedly had some kind of mental breakdown. In 1956, an FBI report stated that informant Eileen Curry had moved to Dallas with her boyfriend James Breen after jumping bail 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 “James got the okay to operate through Ruby of Dallas.” This information had reportedly been known to the Federal Bureau of Narcotics from an informant. Dallas Sheriff Steve Guthrie told the FBI that he believed that Ruby “operated some prostitution activities and other vices out of his club” 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”.

In 1958, an alleged letter by Ruby was sent to the State’s Office of Munitions Controls requesting permission to negotiate the purchase of arms and ammo from an Italian firm. In May 1958, Norman Rothman started smuggling arms to Fidel Castro, with Ruby suspected to have been involved. A “Jacob Rubenstein” was allegedly named in a 1959 Army Intelligence file regarding arms dealers.

In 1959, Ruby traveled to Cuba, allegedly on a simple pleasure trip to meet Lewis J. McWillie, who worked for Santos Trafficante and having ran gambling houses in Dallas until moving to Havana in 1958. On July 8, 1959, Castro released Loran Hall, Henry Saavedra and Santos Trafficante from jail. It has been speculated that Ruby had some role in the release and had even met with Santos Trafficante.

From 1949 to 1963, Ruby had nine criminal charges, ranging from assault to violating state liquor law. Ruby was said to heavily in debt and tended to be violent, getting into fights. He never married and had no children. At the time of the assassination, Ruby was living with George Senator, who referred to Ruby as “my boyfriend” during the Warren Commission hearing, although he denied the two were homosexual lovers.

The Kennedy assassination

On August 29, 1962, a man named Robert Perrin apparently committed suicide in New Orleans. His wife, Nancy Perrin Rich, had worked for Ruby in Dallas at the Carousel Club and after having a falling out with him had linked him to anti-Castro operations. She was a police informant and testified to the Warren Commission while being followed by unknown persons.

In January 1963, Ruby sought out one Gail Raven. Between September to October, 1963, Ruby allegedly met Johnny Roselli. During October, Ruby made a number of interesting contact, including Irwin Weiner, Robert Barney Baker, Nofio J. Pecora, Harold Tannenbaum, Lewis J. McWillie, Murray Dusty Miller, and Lenny Patrick. He made a phone call to Pecora on October 30.

President Kennedy was assassinated by Oswald on November 22, 1963.

The Oswald Assassination

On November 23, 1963, Ruby made a call to his friend Ralph Paul, talking about a gun. Paul contacted Tom Howard. Ruby was present in the press room with Oswald, where he corrected DA Henry Wade with regard to the proper name of the FPCC.

On November 24, Ruby got a call to go to the Western Union to make a wire transfer to a stripper from his club. Soon thereafter, he made his way to the City Hall where he fatally shot Oswald. He was approached by Tom Howard, who began acting as his initial defense attorney. A meeting at Ruby and Senator’s apartment took place that night, lawyer and journalists who were looking for information on Ruby. Lawyer C.A. Droby, who’d been at the apartment meeting, was heavily intimidated to prevent him from becoming a lawyer of Ruby.

Aftermath of the Oswald assassination

The killing of Oswald immediately fueled speculation of a conspiracy. On November 25, a certain “Gaudet” phoned the New Orleans FBI field office giving them covert information that Ruby had purchased painting from an art dealer in the French Quarter.

By December 1963, Ruby began requesting he get a polygraph test. Strange deaths soon began taking place. By January 23, 1964, a witness to Oswald fleeing the Tippit murder scene was shot in the head, but managed to survive. A suspect was immediately picked up, one Darrell Wayne Garner, but eventually an alibi by a woman named Betty Mooney MacDonald, who claimed to have worked as a stripper at the Carousel Club, sprang Garner from jail. On February 23, MacDonald was put in jail on public disturbance charge, but committed suicide in City Hall by hanging herself with her trousers. In March 1964, Ruby was sentenced to death by the electric chair.

On April 23, 1964, Bill Hunter, a journalist in California who had been in Ruby’s apartment on the night of November 24, 1963, was “accidentally” shot by a cop who was supposedly just messing around with another cop. On April 26, 1964, Ruby was visited by Dr. Jolyon West, who concluded Ruby was psychotic. On May 11, 1964, Ruby was given a psychiatric evaluation, but he continued to want a polygraph test. On June 7, 1964, Ruby gave testimony to the Warren Commission, where he pleaded to be taken out of Dallas to Washington D.C., where he wanted a lie detector test to “tell the truth.”

On July 18, 1964, Ruby was given a polygraph test, where he claimed to have not acted on behalf of a conspiracy and to have never done any business with Castro. FBI polygraph expert Bell P. Herndon claimed Ruby passed with flying colors, but scrutiny has been made about the way it was conducted.

On September 19, 1964, Jim Koethe, a Dallas journalist who had been at the Ruby apartment on November 24, was murdered by an apparent burglar who strangled him. Supposedly notes of his for a book on the JFK assassination went missing. A suspect, Larry Earl Reno, was defended by lawyer Jim Martin, who had been at the apartment meeting and later help put Reno in prison. Later in 1964, Ruby kept alluding to higher powers and implicating LBJ in the assassination and expressed guilt over Castro operations.

In March 1965, Ruby was recorded making claims of a possible conspiracy and involvement of LBJ. On March 27, 1965, lawyer Tom Howard died from a heart attack. On July 12 through 16, 1965, Ruby told psychiatrist Dr. Warner Teuter that he was part of a conspiracy involving high government agencies, but Teuter doubted these claims. Ruby was paranoid of being spied on, becoming obsessed with secrecy. He considered himself a victim of a conspiracy to “frame” him in the killing of Oswald, so he could never say who ordered him to kill JFK. He believed the stripper he requested the Western Union wire transfer to be part of the plot. He believed high government agencies and his own lawyers were part of the plot. He was afraid for his life and extremely sensitive over anti-semitism, thinking jews were being tortured and killed as a result of his killing of Oswald

On September 4, 1965, Rose Cheramie, an underworld informant who allegedly predicted the JFK assassination and claimed to have worked for Ruby’s Carousel club and claimed Ruby and Oswald were homosexual partners, died when being ran over by a car in Big Sandy, Texas. She also implicated Ruby in a drug trafficking networks. On September 9, Ruby complained in a recording about not being given a polygraph test during his Warren Commission testimony.

On November 8, 1965, journalist Dorothy Kilgallen died from alcohol barbiturates overdose. He friend, Florence Pritchett died from a cerebral hemorrhage on November 10, 1965. Supposedly she’d been given noted by Kilgallen that went missing.

On January 1966, Earlene Roberts, the Oswald rooming house lady linked indirectly to Jack Ruby via her sister Bertha Cheek, died from a heart attack.

October 5, 1966, Ruby’s conviction was overturned and a new trial was set for February 1967 in Wichita Falls, Texas. In mid-October, Dr. Julian Mardock found Ruby to be in good health, however he began vomiting and coughing up blood. A new doctor, John W. Callahan began seeing Ruby. Sheriff Al Maddox was apparently given a note by Ruby, where he claimed that there was a conspiracy in the assassination and that he’d been injected with cancer.

By mid-November, 1966, Ruby’s health condition worsened, but Dr. Callahan continued to treat him for a cold, despite signs of something much worse. Ruby’s family began to get worried, saying Ruby’s looked like a corpse.

On December 9, 1966, Dr. Callahan though Ruby’s condition was improving, but Ruby demanded an x-ray, so he was transferred to Parkland Hospital. On December 10, 1966, Ruby was diagnosed with end stage lung cancer, also having a massive seemingly unrelated blood clot that moved to his lungs. Ruby’s sister did not trust the prison doctors or Parkland. On December 19, 1966, Ruby insisted he was not part of any conspiracy and that he acted alone in killing Oswald.

On January 3, 1967, Ruby, 56, died from lung cancer and a coinciding blood clot, at Parkland Hospital, in Dallas.

Ruby connections

Strange deaths linked to Ruby continued to take place, even after his death. He was suspected to have been linked to mobsters Sam Giancana, Jimmy Hoffa and Johnny Roselli, who all were murdered in the 1970’s. He also allegedly was linked to Santos Trafficante and Carlos Marcello. Ruby has contacted Pecora before the assassinations, a lieutenant of Marcello, who was allegedly linked to Dutz Murret, Oswald’s uncle. Ruby was also said to have been friends with Sam and Joe Campisi, who allegedly were Marcello lieutenants. Allegedly, Ruby worked for Al Capone in Chicago, running numbers. Roselli made claims about Ruby being linked up with Trafficante. John Wilson-Hudson claimed to have seen Ruby meeting with Trafficante. Luis Kutner claimed Ruby hobnobbed around Sam Giancana.

Hitman David Yaras claimed a Sparky knew Lenny Patrick and could pick up girls. Allegedly Yaras and Ruby were youth friends and Ruby had spoken to Robert Barney Baker a few days before the assassination. Yaras was murdered in 1974.

Jim Garrison implicated Clay Shaw, David Ferrie and Lee Oswald with Jack Ruby. It’s also been alleged that Ruby was linked to Guy Bannister and Ferrie in Cuban casino ventures before the fall of Batista and in the Schlumberger-Double-Chek gun-running, first to castro and then to anti-Castro Cubans. Ruby has also been implicated in New Orleans prostitution with Gordon Novel, David Ferrie and Clay Shaw.

George Carter allegedly got a lead from Tom Howard that Ruby was linked to Thomas Eli Davis in gun running operations. Ruby was even allegedly linked to Frank Sturgis in pro-castro operations. FBI informant Blaney Mack Johnson implicated Ruby with Eddie Browder, linked to Sturgis, suspected associate of Norman Rothman, in arms traffic into Cuba. Robert McKoewn allegedly met Ruby and linked him jeep sales into Cuba.

Richard Randolph Carr, who spread disinformation about the Kennedy assassination, was reportedly linked to Ruby. Others allegedly linked to Ruby include James Henry Dolan and a certain Vaughn witnessed by Napoleon J. Daniel meeting Ruby, also a Meyer Penitz.

Ruby has also been linked to the Dallas Police Department, who had members going to his club.

Notes