Feature Articles

April 2002

The Lost Boy

Jack Ruby and the murder of Lee Harvey Oswald

By John William Tuohy

     By 1962, the American Mafia learned that the Kennedys were as opportunistic and as vicious as they were. The began to understand that the Kennedys played by a set of "rules" that best suited their needs, and in mid-1962, what best suited the Kennedys' needs was the annihilation of the national syndicate, although, they had probably mapped out a strategy on how to deal with the outfit, years before they entered the White House, and a large part of that strategy hinged on Robert Kennedy becoming Attorney General of the United States.

     Like everyone else in America, the mob assumed that Kennedy would name Ramsey Clarke Jr. as his Attorney General, which would have been a stoke of luck for the outfit because when Clarke's father had been A.G. under Truman, the mob prospered. As Murray Humpreys said, "Attorney General Tom Clarke was, he always was, 100% for doing favors."

     But Kennedy stunned everyone when he named his brother, Robert, as Attorney General, at 35 the third youngest Attorney General ever. Los Angeles gangster Micky Cohen summed up Kennedy's appointment for the entire mob when he said, "Nobody in my line of work had no an idea that he was going to name Bobby Kennedy attorney general, that was the last thing anyone thought."

     The mob wasn't sure where it stood with Robert Kennedy until his first press conference as Attorney General, when he announced that as his top priority, the Justice department was going after organized crime: "If we do not," Kennedy said, "on a national scale, attack organized criminals with weapons and techniques as effective as their own, they will destroy us."

     Kennedy was never clear on who he meant by "us."

     True to his vow, Kennedy went after Organized Crime on an unprecedented scale. With the single stroke of a pen, he increased the DOJ organized crime unit by 400% by assigning it sixty new lawyers to work on twenty-seven major Mafia cases.

     He personally developed a "hit list" that grew from 40 names at its inception, and ended with 2,300 names by the time Kennedy resigned from office. According to John Kennedy, Bobby had already drawn up the list before he took over the Justice Department and the Chicago outfit, the branch of the mob that the Kennedys were most indebted to, was at the very top of Robert Kennedy's list.

     So while the Kennedys took their favors from the Chicago outfit, before and after the election, during Robert Kennedy's first week in office, he ordered an increase in the number of FBI agents in Chicago assigned to organized crime to be increased from five to fifty men. To nail the hoods, Kennedy drafted sharp, vicious young men to work in his anti-racketeering center, replacing most of the lawyers at the Justice Department "who have been here since Homer Cummings hired them," cracked a reporter. Kennedy's instructions to his new team were clear: "Get the job done, don't let anything get in your way, if you have a problem come and see me directly, again, get the job done, if you can not get the job done...get out."

     When challenged to define organized crime Robert replied, "Don't define it, do something about it."

     To get the job done at the Justice Department's Criminal Division, Kennedy brought in Jack Miller to run things. Miller, said one of his coworkers, "would not hesitate to indict a man for spitting on the sidewalk if he thought it was the best he could get."

     Kennedy personally fought hard for, and secured, legislation originally proposed by the Kefauver committee, but ignored by Congress, to fight organized crime on a national basis. Kennedy made sure a secure friend was placed in charge of the IRS, a friend who understood Kennedy-think; meaning that the sole purpose of the IRS was not to raise money for the government but to harass gangsters, and, as it turned out, anybody who annoyed the Kennedys. As a result, IRS man-hours of participation in organized crime cases rose from 8,836 in 1960 to 96,182 in 1963.

     The results were staggering. Kennedy's Justice Department was able to bring 288 tax cases against the estimated 5,000 Mafioso operating in the United States in 1963.

     It wasn't out of any great hatred for crime that motivated Robert Kennedy to go after the mob; he went after the mob for self-preservation. Rather, it was a race for life and Kennedy was desperate to win it by striking first. As John Kennedy told writer Jack Anderson, he was aware that the mob had stolen the election for him and that as a result, he needed to attack the outfit to show that he was not beholden to them.

     Like his brother and father, Robert Kennedy was terrified over the thought that organized crime would come around to the White House with its hand out, and when it did, they chopped it off.

     The once structured world of organized crime was collapsing around them. All across America, hundreds of hoods were under investigation or indictment by the Justice Department, under surveillance by the FBI, and most dangerously of all, their enormous incomes were scrutinized by the Internal Revenue Service. In Chicago, the Immigration Service was deporting Paul Ricca, the IRS was hounding Tony Accardo and a conviction looked positive, Sam Giancana was lockstepped, the outfit's private piggy bank, the Teamsters pension fund was under scrutiny, as were the casinos it built, and Jimmy Hoffa was going to jail. It was so bad that Joey Auippa, one of Giancana's best soldiers, was arrested under the Federal Migratory Bird Protection Act after Federal Agents found edible doves in his freezer. It wasn't going to end either. Everyone agreed that Kennedy would easily win reelection against Barry Goldwater, Willie Bioff's old pal, in the 1964 election. It was killed or be killed, and for the bosses, it was a simple selection, they would have to strike first, they would have to kill the President of the United States.

Enter Jack Ruby.

     It's a twist of fate that the Chicago outfit's assault on the city's labor union in the late 1930s would be the eventual cause of driving Jack Ruby out of Chicago's west side, to Dallas Texas, and into infamy.

     Chicago's crowded west side -- it had 50,000 residents per square mile when Jack Ruby was a boy there -- was home to some of Chicago's most colorful and poverty stricken ethnic enclaves, including the largest Jewish population in North America.

     Jack Rubenstein, Ruby's given name, was born here in the once notorious Lawndale district, near Maxwell Street. Ruby's childhood years were a fitting portrait of life in Lawndale. His father, Joseph, was an abusive, heavy drinker, who beat his much younger wife, Fanny Rokowsky, the couple having been tossed together in an arranged marriage, then commonplace in their native Poland. Fanny Rubenstein, Jack's mother, was a women plagued with her own demons, who often beat and verbally abused her children. A quick-tempered redhead, and the daughter of respected doctors, she was uneducated, crude and emotional. Eventually, unable to control her outbursts, she was committed to a series of mental asylums, causing the family to break apart when Jack was just ten years old, although he lived on and off with his mother when she wasn't hospitalized.

     Ruby seldom attended school classes, and as a result, he flunked out of 3rd grade, although he later claimed to have finished the 8th grade. Instead, Ruby and his childhood friend, Barney Ross, who would go on to be one of the toughest prize fighters ever to rule the ring, were street hustlers, scalping sports tickets and doing anything else they could to earn a living, including running numbers for Al Capone's minions, occasionally delivering payoff envelopes to the police and prosecutors downtown. Ruby quickly grew into a tough kid and earned a reputation as an awesome street brawler who, win or lose, never backed down. In 1923, under court order, Ruby and his brother and sisters were taken from their parents' care and submitted to the care of foster homes for several years, but foster homes didn't change Ruby much. He still roamed the streets, still fought and still got into trouble.

     In 1933, Ruby and several other teenagers from the neighborhood traveled to California, ending up in San Francisco selling horse racing tip sheets at a mob-owned track. It was here that he may have become involved in the outfit's little known but very lucrative marijuana smuggling operation out of Mexico into Los Angeles. Ruby returned to Chicago in 1937, and became involved with the Scrap Iron and Junk Handlers Union, local 20467, where he worked, for $22.50 a week, as an enforcer and strong-arm goon, although his official titled was union organizer.

     The local was organized by Ruby's friend and mentor, Leon Cooke, a lawyer by training, whose chief goal was to raise wages for the membership to something more reasonable then the 15 cents an hour they were making. But in the late 1930s labor plundering was the Chicago outfit's chief source of income, so when Johnny Martin, a two-bit hustler associated with the Chicago syndicate's leading labor plunderer, Murray Humpreys, came to Humpreys for permission to take over the Scrap Iron Workers, Humpreys gave his permission.

     Within days, Martin, with the mob behind him, had moved in on the union and appointed himself President. At the time, Martin was also on the City of Chicago's payroll as a Sanitary District Clerk and was under indictment with mob boss Paul Ricca for trying to hide taxable income from the federal government.

     Jack Ruby, although hired by Cooke, soon fell under Martin's command and was made the syndicate's bagman inside the union.

     As for Leon Cooke, no one is really sure what happened, except that there was a power struggle within the union, and Cooke ended up shot dead.

     From what police were able to reconstruct of the crime, Cooke barged into Martin's office and told him he wanted him out of the union. Martin argued back. After a few minutes, Martin drew a revolver and shot Cooke three times in the back, and then took the only witness to the shooting, the office secretary, as his hostage, and fled down a back staircase. Eventually Martin was arrested and released, claiming self-defense although he couldn't explain, nor did the state's attorney office ask why, if it was self-defense, Cooke was shot in the back.

     For the first few days after the shooting, Jack Ruby was the primary suspect in the incident and was even picked up and questioned by police about his role in the murder, but was released after two hours. Later, in an odd twist of fate, Robert Kennedy reinvestigated Ruby's role in Leon Cooke's killing for the McClellan committee, and concluded that Ruby played no role in the murder, but noted that the Cook County State's Attorney chief investigator, the notoriously corrupt Tubbo Gilbert, moved in on the union shortly after the shooting, and confiscated all of the unions records and charters. Those documents, along with all police records pertaining to the Cooke shooting, Kennedy noted, disappeared for ever and so Jack Ruby's real position within the Union will probably never be known.

     After Leon Cooke's murder, Jack Ruby hit the streets and started telling people that he intended to take over the union, but it was all talk. Most things about Jack Ruby were all talk. Besides, the syndicate had its own plan for the Junk handlers. The union was renamed the Waste Handlers Material Union, local 20467 of the American Federation of labor, and in 1939, Paul Dorfman, one of the syndicate's chief labor racketeers, was moved in to run the operation, causing the AFL-CIO to dub the local "largely a shakedown operation."

     Ruby stayed on with the union as its bagman under Dorfman for several more months before leaving to work with for Ben Zuckerman, also known as "Zuckie the Bookie," a gambling big shot who was a power in the 24th Ward and was connected with "Dago" Lawrence Mangano, a Mafia hood with high ambitions.

     In the summer of 1944, Mangano and his crew made their move against the mob's acting Boss, Paul Ricca, but Ricca moved first and gunned down Mangano and his partner Mike Pantillo and then killed Zuckie the Bookie and his financial backer, Willie Tarsch. The killers are thought to have been two mob associates named Lenny Patrick and Dave Yaras. Many years later, Congressional investigators wrongly assumed that Ruby was run out of Chicago by Lenny Patrick for operating one of Zuckie's handbooks on Patrick's territory, without permission, and that Patrick gave Ruby 24 hours to clear out of Chicago. It was an impressive story, one that Ruby often told himself, but it probably wasn't true. Like most syndicate hoods, Lenny Patrick was all about money and nothing else and he wouldn't have run Ruby out of town, a good handbook operator is hard to find. Instead he would have let Ruby off with a warning and then put him to work on a 60-40 split.

     If Ruby was run out of Chicago, it was probably because he wasn't a producer, a money maker or because he was skimming from the take before giving Patrick his cut. But all the evidence points to Ruby not having been chased out of Chicago, but rather being recruited out to represent the outfit in Texas.

     In 1947, Ruby had followed his sister, Eva, to Dallas where she had opened a nightclub/restaurant called the Singapore Super Club, a name borrowed from a notorious mob hangout on Rush Street in Chicago. After Ruby bought the place, he changed the club's name to the Silver Spur.

     Ruby reappeared in Chicago in 1949, when his name showed up on a list of potential informants willing to work with the Kefauver committee while it was in Chicago. The Committee's lawyer, Lou Kutner, who was accused of accepting $60,000 to make sure that the committee didn't call the Chicago mob's leadership to testify on specific issues, arranged for Ruby to meet with the committee's chief counsel, Rudolph Halley. Halley noted to Kefauver that "Ruby is a syndicate lieutenant who had been sent to Dallas to serve as a liaison for the Chicago mobsters" and that "Ruby was the payoff man for the Dallas Police department."

     As unlikely as those facts might be, Ruby failed to provide the committee with any information causing Halley to suspect that the hood, with Kutner's knowledge, had been sent to him by the syndicate to provide the committee with false information.

     A few years after Ruby left Chicago for Dallas, gangster Sam Giancana took over the policy rackets in Chicago's enormous Black ghetto and the mob began to understand just how much money there was in penny and nickel gambling. Inspired by the fortune they were soon taking out of Chicago's poorest neighborhood, Tony Accardo, the acting boss, ordered the boys to capture the policy racket on a nationwide basis.

     Before the end of 1946 the Chicago outfit's gambling arm was active in Iowa, Kansas, Indiana, Michigan and then turned an eye on Dallas, Texas which was a logical move for the outfit. Dallas was a wide open, rich city that supported an enormous gambling and prostitution racket run mostly by freelancers. Accardo had paved the way for a takeover by corrupting Will Wilson, District Attorney, and had, through Eddie Vogel, the old Capone slot machine distributor, put up $168,000 to help elect Governor Beauford Jester. Now Accardo wanted to make sure that Dallas County Sheriff Steve Guthrie was with them as well. To find out, Accardo sent Pat Manno, a crew boss from Chicago's North side, and two small-time fixers named Paul Jones and Jack Nappi, went down to Texas, with orders to get in touch with Guthrie and bribe him so the outfit could move in and organize the city.

     One of the first things Jones did when he arrived in Dallas was to get in touch with Jack Ruby, later telling the FBI that he contacted Ruby because he had been given assurances by mobsters Jimmy Weinberg and Paul "Needle Nose" Labriola that "Ruby is all right, he's with us" but it's more likely that Jones looked up Ruby because he had been doing business with his brother Hyman for decades.

     In fact, the week before he was arrested for trying to bribe Sheriff Gutherie, Jones arranged for Hyman Ruby to distribute 70 gallons of whiskey into the dry state of Oklahoma, while out on appeal he had several meetings with Ruby's sister Eva, whose boyfriend was involved in a bait and switch scam. Both Eva and Hyman said they had known Jones since 1945, and Federal agents suspected that Jones and Hyman operated an opium smuggling operation out of Mexico and had hauled them both in for questioning. Later that year, Jones was arrested for importing one million dollars, in 1945 currency, worth of opium across the border at Piedra Negras.

     After a few days of following Sheriff Gutherie around town, Jones approached him on the golf course and after some chit chat asked "How would you like to make some real big money?" The Sheriff said he was interested and Jones promised him $150,000 a year if he cooperated with the syndicate when once it started to operate slot machines and floating crap games in the city. But, right after the game, Gutherie went to the Texas Rangers for help and was provided with recording devices and a photo surveillance team who collected enough information over the next few months to send each of the hoods involved to prison for a decade.

     Gutherie said that during one of the meetings that Jones named Jack Ruby, whom he knew, as the man who would be brought in to run the Dallas operation for Accardo. Two decades later, when Gutherie reported that information to the Warren Commission, FBI agents were sent to retrieve the four tapes made of the conversation, but two of the tapes, including the one where Jones named Ruby as his contact man, were missing. Gutherie knew Ruby of course, which was probably why the hoods tossed his name into the bribery attempt. "Anytime I wanted to find any member of the syndicate who was doing business in Dallas," Sheriff Gutherie said, "I just went to look for them at Jack Ruby's Silver Spur."

     A month before he gunned down Lee Harvey Oswald, Jack Ruby met with Johnny Roselli in Miami and later with Frank Caracci, a member of Carlos Marcello's mob, in New Orleans. Later that month, Ruby was in regular phone contact with Nofio Pecora, an ex-con and Marcello associate with a history of dealing in international narcotics who also ran a call girl service between New Orleans and Mississippi. Pecora's brother-in-law was Marcello's front man in several legitimate operations and Pecora's wife, who was Marcello's personal secretary, was also the sister-in-law to Joey Poretti, who managed Marcello's real estate holdings.

     Another person Ruby was in phone contact with just before the assassination was Irwin Weiner, the "favorite front man of the Chicago outfit." At the time, Weiner, who lost holdings in Havana, including a large share in the Deauville Casino, was under a federal indictment on a Florida fraud charge with a major Chicago Capo named "Milwaukee Phil" Aldersio, who would have a short reign as Chicago's boss in the late 1960s.

     Years later the government would indict Weiner on the grounds that he helped Jimmy Hoffa loot the teamsters' pension funds, but the charges were dropped after the government chief witness was shot to death while his family watched. Called before the Warren Commission to explain the flurry of phone calls he took from Jack Ruby, just prior to the Kennedy assassination, Weiner said: "Ruby was a friend of mine. He called me. I talked to him. What I talked to him about was my own business. And I just don't want to, don't feel that I should, discuss it with anyone. It has no relation, no bearing on anything." Remarkably, the Commission accepted Weiner's answers and never looked into his background or examined his ties with organized crime. Even more remarkably, the Warren Commission concluded that it "believes that the evidence does not establish a significant link between Ruby and organized crime."

     After he fired the fatal shots that killed John Kennedy, Lee Harvey Oswald was probably supposed to disappear into the crowd and confusion below him in Dealy Plaza, and then walk calmly and slowly to Jack Ruby's apartment, where, as the Warren Commission's David Berlin said, Ruby was to provide Oswald with a passport, a bundle of cash and a ride down to Mexico. Robert Kennedy, in discussing the Ruby shooting, said that "it's impossible that Oswald and Ruby didn't know each other."

     Of course, they would never have allowed Oswald to live, only Oswald was naive enough to believe that. They would gun him down the second that they could and dump his body in a lime pit some place. But it never happened, Oswald was arrested, and the police had the man who could directly tie the mob into the biggest murder in American history. After that, Jack Ruby was a dead man. He had fouled up the biggest contract ever handed out by the bosses and unless he fixed it he was a dead man. He had no choice left. He would have to finish the job himself.

     The prosecution would never be able to prove that Ruby had prior knowledge of Oswald being moved from one jail to another, so, at worse, Ruby would be accused of an impulse shooting. He would even have an excuse to have a pistol on him, since Texas law allowed any business owner who was carrying the day's cash proceeds to or from his place of business to arm himself with a pistol, so on the day Ruby shot Oswald, he made sure he was carrying a day's proceeds to the local western union office to wire money to a stripper who worked for him. That would also give Ruby an excuse to be in the area of the police station since it was only a block from the western union office, and the police would help since the outfit owned large parts of the drastically underpaid Dallas Police force.

     A police Captain recalled: "The department had a long history of being rotten at its core, I mean from top to bottom. Oh, there were some good cops. But man, it was a dangerous place to work in. You never knew which side your boss or partner was on. There was plenty of money floating around, all you had to do was rise your hand."

     Someone raised their hand. Someone called Ruby from inside Police headquarters and told him exactly when and where Oswald would be moved. Slipping into the heavily guarded Dallas Police Department garage was easy. Ruby cultivated cops, a lot of cops over the years, and the cops had also cultivated him as an informer. Once inside the garage, shooting Oswald was easy, there was no protective flank around Oswald as he was strolled, slowly, through a crush of reporters, and the car that was supposed to transport him out of the building never arrived anyway.

     On November 24 at 11:20 A.M., Jack Ruby lunged out from behind a Dallas policeman that he had known for decades, and fired his .38 Colt Cobra into Oswald's abdomen silencing him forever.

     When the Police hauled Ruby away from the murder scene, not far from the hallway where Oswald shouted out to the press, "I'm just a patsy," Ruby shouted out, "I've been used for a purpose."

Mr. Tuohy can be reached by writing to

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