Chicago Mob Stories:
Jack Ruby, Organized Crime and the Kennedy Assassination
by Richard C. Lindberg & John William Tuohy
Copyright © 2002

In 1937, Jack Leon Rubenstein, a minor hood and fringe gambler living on the edge, crept back into Chicago after a brief, and failed attempt to establish himself as a big-time wheeler-dealer in California. He had worked as a singing waiter in L.A., and a salesman peddling newspaper subscriptions in San Francisco, none of it to his liking.

Ruby, who would leapfrog into the pages of history as the assassin of Lee Harvey Oswald, struggled financially in one disastrous scheme after another until he partnered with one Harry Epstein in a punchboard business cleverly disguised under the trade name Superior Products Company. Virgil Peterson of the Chicago Crime Commission drew law enforcement's attention to the existence of this illegal enterprise, but subsequent inquiry failed to establish Ruby's connection to the business and the investigation foundered.

More gainful employment for Ruby emerged with the American Federation of Labor Scrap Iron and Junk Handlers Union, local 20467. Ruby was hired as an "enforcer" (a paid goon), although the official title given him was a more dignified sounding "union organizer." His drew a modest salary of $22.50 a week.

Union treasurer Leon Cooke mentored Jack Ruby, although we only have Ruby's assurances on that point. In 1937, Cooke was a 25-year-old labor lawyer who founded the Chicago local in order to raise wages for junk handlers from 15 cents per hour to a more reasonable living wage.

Johnny Martin, a hustler associated with gangster Murray "the Camel" Humphreys, muscled in and appointed himself union president ending all pretense of a clean and honest local. At the time, Martin was also on the City of Chicago's payroll as a sanitary district clerk and under indictment with Paul Ricca for hiding taxable income from the federal government.

Ruby, meanwhile, had fallen under Martin's spell and became his bagman within the union.

A power struggle within the union soon developed, and Leon Cooke was fatally shot on December 8, 1939. As he lay dying, Cooke identified Martin as the source of his present difficulties, but he did not implicate Jack Ruby. Cooke lingered until January 5th.

From what police were able to piece together, Cooke had barged into Martin's office and demanded his resignation from the union. The two men exchanged heated words. After a few minutes, Martin drew a revolver and fired three rounds into Cooke's back and then seized the only witness to the shooting, the office secretary Mrs. Gladys Walsh. The pair fled down a back stair well. Eventually Martin was arrested and released after claiming self-defense although he couldn't adequately explain, nor did the state's attorney office ask why, that if it were a case of self-defense, why was Cooke shot in the back?

Acting on orders from Murray Humphreys, the notoriously corrupt State's Attorney chief investigator Dan "Tubbo" Gilbert moved in and confiscated all of the union records and charters. The records and other important documents relating to the case have long since disappeared. Gilbert, sarcastically dubbed "the Millionaire Cop," later ran for Cook County Sheriff and lost.

A coroner's jury returned a verdict of "justifiable homicide" in the Cooke slaying.

With Cooke out of the way, the union was renamed the Waste Handlers Material Union local 20467 of the American Federation of Labor. In 1939, Paul "Red" Dorfman, one of the syndicate's important labor racketeers, was brought in to run the operation. Chagrined by these developments, the AFL-CIO threw up its hands in frustration and described the local as "a shakedown operation."

Until he was ousted from the junk handler's union in 1957 by the AFL-CIO, "Red" Dorfman was the conduit between the mob and big labor. He introduced the late Jimmy Hoffa to the syndicate factotums as someone Chicago "could do business with." His son Allen became the high priced insurance "consultant" to the Central States Pension Fund until his assassination in a hotel parking lot on January 20, 1983.

The rumors surrounding the Cooke murder did not officially end with Martin's exoneration. Jack Ruby was picked up by the States Attorney's police as a suspect in the shooting not long after Cooke was transported to the hospital. But after two hours of questioning he was released. Ruby hit the streets and boasted that he intended to take over the union. He was always shooting off his mouth that way, and was impressed with his tough guy stature.

Later, in an odd twist of fate, Robert Kennedy would re-investigate Ruby's role in Leon Cooke's killing before the U.S. Senate-McClellan Committee hearings in 1959.

Ruby faithfully served Dorfman for several more months before launching the Spartan Novelty Company with his brother Earl in early 1941. Through bad planning and poor timing, the venture failed. Ruby returned to his old poolroom haunts in Lawndale on the Jewish West Side to see what would turn up next. He did not have to wait long.

Eventually Ruby drifted into the orbit of the "Jewish faction" of Chicago organized crime where Ben "Zookie the Bookie" Zuckerman was the major domo along Roosevelt Road.

Zookie was a gambling big shot in the 24th Ward; the domain of Alderman Jacob M. Arvey, who employed Ruby's brother Hyman for minor chores. Arvey, a notorious political fixer who turned out record numbers of Democratic voters in every city election he was personally involved with, served as alderman of the West Side ward from 1934 until 1940.

Zuckerman, with Arvey's blessing, took over the gambling concession in the ward. He was backed by "Dago" Lawrence Mangano a hood with high ambitions. But on August 3, 1944, Zookie's crap-game partner Mangano and a police character named Mike Pantillo were shot gunned to death in an inter-gang dispute. Paul "the Waiter" Ricca, head of the traditional Italian faction of Chicago "O.C." was held responsible.

With Mangano conveniently out of the way, Ricca and Accardo disposed of another Zuckerman partner, Willie Tarsch (alias "Willie Kolatch") in the rear or a building at 3710 West Roosevelt Road on April 7, 1945. A wave of bombings followed, creating havoc and disrupting gambling operations in the neighborhood for weeks to come.

Zookie the Bookie ended up on a slab in the morgue after Lenny Patrick and Dave Yaras shot-gunned him outside his West Side residence at 4042 Wilcox Street on January 14, 1944. When Zookie's partner Ben Glazer heard what had happened, he dropped dead from a heart attack. (Note: See Rich Lindberg's book "Return Again to the Scene of the Crime: A Guide to Even More Infamous Places in Chicago" for further details of this crime).

It was whispered by Congressional investigators that Ruby was been run out of Chicago by Lenny Patrick as punishment for running one of Zookie's handbook in Patrick's territory without Patrick's express permission. It was rumored that Patrick, as titular head of the "Jewish Faction," gave Ruby twenty-four hours to clear out of Chicago. It was an interesting story but probably fiction. Like most syndicate hoods, Lenny Patrick was all about money and nothing else. In the end, he would have put Ruby to work for him on a 60-40 spilt.

Patrick always denied the allegation of a close association with Ruby. "No matter how much you investigate," he told the Warren Commission "you'll never learn nothing as he never had nothing to do with nothing."

If Ruby was in fact "run out of Chicago" by Lenny Patrick, it was for no other reason than Ruby just wasn't a very good earner. Throughout his lifetime, Ruby struggled to make ends meet. He was a consummate failure in every business enterprise he launched, legitimate or otherwise.

Jack Ruby was a self-absorbed braggart who liked to impress others with his bravado and connections with celebrity gangsters. He bragged to his customers in Dallas that he had been "run out of town" by Chicago mob figures. It was an intriguing story told to the barflies of the burlesque houses. He was a colorful but by the same token a mentally unbalanced loser who imagined that a sinister anti-Zionist, anti-Semitic cabal of zealots were plotting acts of violence against the Jewish people.

A year after his honorary discharge from the Army in 1946, Ruby followed his sister Eva Grant to Dallas where she had opened the Singapore Supper Club, a nightclub/restaurant with swanky pretensions, named in honor of the well-known mob hangout on Rush Street (later owned and operated by bookmaker Marshall Caifano the Chicago mob's "point man" in Las Vegas, and one of first gangsters to be listed in the Nevada Gaming Control Board's "black book" of undesirables). Sam "Teetz" Battaglia, out of the West Side "Valley" region was another partner in the operation.

Ruby agreed to manage the club, but he later changed the name of the place to the Silver Spur, featuring a Country & Western decor. He had an interest in six different nightclubs in Dallas over the course of sixteen years, including the Club Vegas and the Sovereign, later renamed the Carousel Club. These gin-soaked buckets-of-blood provided Ruby's loyal customers with cheap thrills, bump-and-grind amusements, and back-room assignations with the exotic dancers.

Late in 1949 Ruby returned to Chicago, volunteering his services as a potential informant willing to work with the U.S. Senate-Estes Kefauver Special Committee to Investigate Organized Crime in Interstate Commerce, scheduled to conduct hearings into local gambling conditions the Fall of 1950.

When the committee arrived in Chicago in September, Ruby had already approached a key committee lawyer named Lou Kutner to add his name to the list of informants. Kutner, who had been accused of accepting $60,000 to ensure that the committee did not subpoena the top Chicago mob leadership to testify on specific issues, arranged for Ruby to meet with the committee's chief counsel, Rudolph Halley.

Halley reported 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." Very interesting, in light of author Gerald Posner's assertions in "Case Closed: Lee Harvey Oswald and the Assassination of JFK," that Ruby's involvement with the Dallas P.D. and the Chicago mob was much exaggerated, after the debate over the existence of a far-flung conspiracy to kill President Kennedy surfaced.

However, Ruby failed to provide the committee with any substantive information and Halley later suspected that Ruby had been sent by the syndicate for the purpose of supplying committee members with false information.

If Jack Ruby was a serious informant, it is likely it would have been his swan song with the mob bosses. But it so happened that around the same time, Murray Humphreys sent a hood named Pat Manno and two small time fixers; Paul Roland Jones, a narcotics trafficker, and Jack Nappi, down to Texas with orders to bribe Dallas County Sheriff Steve Guthrie to allow Chicago wider latitude in local vice and gambling.

Dallas was becoming a playground for made Chicago guys who ran various rackets all over town. Ruby, Sam Yaras, Nick DeJohn, Joe and Rocco Fischetti had interest in the lucrative jukebox and pinball action with Eddie "Dutch" Vogel, former czar of coin operated "amusement devices" back in Chicago.

Paul Jones later told the FBI that when he arrived in Texas, he was assured by mobsters Jimmy Weinberg and Paul "Needle Nose" Labriola that, "Ruby is all right, he's with us."

After a preliminary rendezvous with Ruby, Jones approached Sheriff Guthrie on the golf course and asked, "How would you like to make some real big money?"

Over drinks, Jones promised the Sheriff a starting salary of $150,000 a year if he cooperated with the syndicate in the placement of slot machines and floating crap games across the city.

Guthrie said he would think it over, and another meeting was arranged. However, the Sheriff was an honest police official who solicited the Texas Rangers for help in fighting the incursion of the Chicago mob.

The next meeting was secretly tape recorded by the Rangers. Jones told Guthrie (who later repeated the story to the FBI), that Jack Ruby was named by Jones as the man who would be brought in to run the Dallas operation for Tony Accardo, and that Ruby would arrive in the Spring of 1947. That coincides with the exact time of year Ruby stepped off the train in Texas.

On November 6, 1946, Pat Manno arrived in Dallas and registered at the Adolphus Hotel. Early the next morning Manno, Paul Jones, Jack Knapp (the syndicate representative in Wisconsin and a nephew to Manno), and Lt. George Butler of the Dallas Police Department, met with Sheriff Guthrie at his residence for nearly three hours. They talked about establishing a nightclub as a front for gambling operations in Dallas, but Ruby's actual role in managing such a place is questionable despite allegations to the contrary. In 1979, the Select Committee on Assassinations concluded that there is no hard evidence that Ruby was the man the Chicago mob had in mind for such a delicate assignment.

Sheriff Guthrie strung the Chicago mobsters along for a month. They were all locked up or booted out of town on December 7.

When authorities arrested the outfit policy king Pat Manno for trying to bribe the sheriff, Manno commented that he had been breaking the laws for decades in Chicago and nothing as humiliating as this had ever happened to him there.

In the weeks before he was arrested, Jones arranged for Hyman Ruby, Jack's brother, to distribute 70 gallons of whisky into the dry state of Oklahoma. At that same time, sister Eva Ruby and her live-in boyfriend were arrested in Dallas on mob connected fraud charges.

Jones knew Eva and Hyman Ruby back in Chicago, when he began running drugs from the Mexican pipeline in 1945. Federal agents suspected that Jones had mailed Hyman or Jack opium via the US mail. The feds hauled them in for questioning but could prove nothing. Eventually, Jones was found guilty of attempted bribery and sentenced to three years in prison.

Many years later, when Sheriff Guthrie repeated the story to the Warren Commission, the committee ordered the FBI 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, turned up missing. In all, 22 of the 42 records made of the meetings have disappeared including all the material mentioning Jack Ruby.

The 1950 Kefauver investigating committee categorized the attempt by the Chicago mob to buy police protection and other considerations in Dallas "...as an extraordinary event; one of the more brazen efforts made during that postwar period of criminal expansion."

The slayer of Lee Harvey Oswald maintained all along that he did it for the sake of the Kennedy family in order to spare them the ordeal of a trial. He said that he casually wandered into the basement of the Dallas Police station on "an impulse" and shot Oswald while seventy-seven armed police officers stood by. Author Posner agrees, contending that this was the desperate act of a grieving, possibly demented man who momentarily lost control of his senses. Others see a far more sinister motive; that security was deliberately breached and Ruby was the hired agent of organized crime bosses assigned to silence Oswald.

Even the Select Committee went on record as saying that "Ruby had probably talked by telephone to [Lenny] Patrick during the summer of 1963," and that he had made three trips to Cuba between 1959 and 1963. "The committee developed circumstantial evidence that makes a meeting between Ruby and [South Florida organized crime boss Santos] Trafficante a distinct possibility."

Whatever the case, Ruby was found guilty of murder on March 14, 1964, and sentenced to death. Paranoid and delusional at the time of his passing on January 3, 1967, Jack Ruby expired as a result of a blood clot. He left behind a raft of unanswered questions for conspiracy theorists to ponder.

What is most intriguing about the Warren Commission conclusion is that Jack Ruby maintained no underworld contacts at all, a view contradicted by the Select Committee on March 29, 1979, when they reported: "The evidence available to the committee indicated that Ruby was not a "member" of organized crime in Dallas or elsewhere, although it showed that he had a significant number of associations and direct and indirect contacts with underworld figures and a number of whom were connected to the most powerful La Cosa Nostra leaders. Additionally, Ruby had numerous associations with the Dallas criminal element."

The Dallas criminal element was under the heel of New Orleans godfather Carlos Marcello. At the time of the assassination, Ruby was involved in slot machines and bookmaking operations controlled by Marcello, none of which was reported by the Warren Commission.

It seems clear that the FBI suppressed evidence of Ruby's connections to leading organized crime figures in Dallas, New Orleans and Chicago.

"The [Select] committee believed that Ruby's shooting of Oswald was not a spontaneous act, in that it involved at least some pre-meditation. Similarly, it was less likely Ruby entered the police basement without assistance, even though the assistance may have been provided with no knowledge of Ruby's intentions."
John Tuohy is a Washington D.C.-based author who recently published a book about his namesake, Gangster Roger "the Terrible" Touhy (no relation). Rich Lindberg is the author of eleven books including Return Again to the Scene of the Crime: A Guide to Even More Infamous Places in Chicago.