To 1939

“The difference between guilt and innocence in any court is who gets to the judge first with the most.”
-Chicago mobster Murray Humphreys

Jack Ruby was born in Chicago in 1911. No one is sure of the exact date of Ruby’s birth, since recording births was not required in Chicago until 1915. Ruby, whose real name was Jacob Rubenstein, was born sometime in March, April or June, according to his school records. The date Ruby used most frequently was March 25, 1911. However, the Dallas Police report for his arrest on November 24, 1963, showed his date of birth as March 19, 1911. His gravestone reads April 25, 1911. Take your pick.

Jack is the fifth of eight children born to Joseph Rubenstein and Fannie Rubenstein, both of whom were Polish Jews who immigrated to the U.S., and settled in Chicago. The father, who was a carpenter, came in 1903. The mother, accompanied by two of their children, Hyman and Ann, came the following year. As was customary in Poland at the time, they had an arranged marriage, so they weren’t necessarily compatible with one another. There seemed to be more loathing than loving in the marriage.

Ruby’s mother, Fannie, was illiterate. She went to night school in 1920 to learn how to sign her name, but apparently failed at the endeavor since she continued to sign her name with an “X” mark in later years. She spoke very little English. Yiddish was the primary language spoken in the Ruby household. Although Ruby’s mother personally lacked an education, she believed it was important for her children, and she argued about it frequently with her husband who thought an elementary school education was about all anyone needed. Arguing was a constant thing in the Ruby household, and not just about education.

Ruby grew up in a Jewish neighborhood near 14th and Newberry streets in Chicago. The apartment was adjacent to an Italian neighborhood, and there were frequent turf battles. This is probably where Ruby developed his street-fighting skills. The family moved frequently, but always within the Jewish neighborhood. All the residents were near the low rung on the economic ladder. Ruby’s father called the area a ghetto.

Ruby’s home life is filled with constant strife. His parents argue constantly, and sometimes it becomes physical. Ruby’s father is arrested numerous times for assault and battery, sometimes because of charges filed by his wife. Ruby’s father drinks excessively and beats his wife and children. Ruby’s mother has a violent temper, and sometimes attacks the father and the children. She hates being a mother, and complains about it in front of the children. She resents the father for getting her pregnant so often.

Jack’s mother also shows signs of mental disease. Two years after Jack is born, she becomes delusional about a sticking sensation in her throat being caused by a lodged fishbone. Each month, she goes to a clinic, and each month the examining doctor tells her that there is nothing in her throat. The sensation is but a figment of her imagination. This goes on for several years.

Jack’s childhood comes right at the beginning of the “Roaring 20s.” It was out with the old, in with the new. Automation was taking hold. The ancient was becoming modern. People are getting rich. It’s a great time to be alive — unless you’re Jack Ruby.

1 roaring 20s
The good times start to roll during the Roaring 20s, but not for Jack Ruby.

Jack’s mother and father separate in 1921. Jack is emotionally scarred from the chaos and turmoil in his life and soon begins displaying signs of trouble. At the age of 11, he is referred to social services for being “truant and incorrigible.” The psychological report indicates that Jack is “quick tempered” and “disobedient.” He frequently disagrees with his mother. He considers her to be an inferior person, and he does not believe he has to comply with her rules. Jack goes on to say that that he runs away from home because his mother beats him and lies to him.

Jack also feels that his classmates pick on him. The few friends he has are young hoodlums like Lennie Patrick and Dave Yaras, both of whom will grow up to be mobsters.

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Jack’s childhood friends are Lenny Patrick and Dave Yaras who will grow up to be mob hit-men.

Although Jack describes himself as a good ballplayer, he doesn’t belong to any clubs and isn’t a member of an athletic team. But he is an excellent street fighter and often boasts that he can lick anybody and everybody in anything he wants to do.
Jack Ruby’s mother is described by Jack’s counselor as being totally incapable of coping with her children. His mother’s extreme temperament and quarrelsomeness are cited as possible causes of young Jack’s bad behavior.

The examining psychologist recommends that Jack be placed in a more wholesome environment outside of the Rubenstein home. At a juvenile court hearing on July 10, 1923, Jack and three of his siblings are ordered into foster care. Court records indicate that Jack lives in foster homes from July, 1923, until November, 1924. However, Jack claims that he spent at least five years in foster homes.

A Young Hustler Hits the Street.

In spite of the fact that he is in and out of multiple foster homes, Jack manages to get through eight years of public school, although he has to repeat third grade. He completes the eighth grade in 1927 when he is 16. Then he drops out of school and hits the streets of Chicago to try to scratch out a living for himself and his family.

3 streets
Jack becomes a hustler on the streets of Chicago to try to scratch out a living for himself and his family.

As an avid sports fan, Ruby gravitates to ticket scalping to earn money. He also sells numerous novelty items and knickknacks, particularly those connected with professional and collegiate sports. Jack is not inclined to work on a steady basis for someone else.

Ruby’s only legal troubles as a youth stem from an altercation he has with a policeman about ticket scalping. His brother Hyman, who is active in local politics, is able to get the charges dropped. However, Ruby does get busted for the unauthorized sale of copyrighted sheet music a few years later and serves a short jail sentence.

Will the Real Jack Ruby Please Stand Up?

When it comes to his personality, Ruby is an enigma. Some of his acquaintances describe Jack as quiet, mild mannered, and even tempered. Former welterweight champion Barney Ross, who knew Jack as a young man, calls him well behaved. According to Ross, Ruby is not a troublemaker and never has trouble with the law. Another friend says that Ruby never starts fights, even though he’s good with his fists, and that he will go out of his way to avoid clashes.

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Former welterweight champ Barney Ross knows Ruby as a young man and later says that Ruby is not a troublemaker and never has problems with the law.

Then there are those who say just the opposite. They know the Jack Ruby who’s hot tempered and quickly moved to physical violence and verbal assault. In the “tough” Chicago neighborhood where Ruby lives, self-defense is extremely important, and Ruby has the reputation of being a good street brawler. He occasionally uses a club, brass knuckles or any other weapon he can get his hands on. One acquaintance describes Ruby as quick tempered and willing to go into a fight without regard to the odds against him.

One example of this comes on October 18, 1929, in Chicago. Eighteen-year-old Jack Ruby is in front of Wrigley Field scalping tickets for the opening game of the World Series between the Chicago Cubs and the Philadelphia Athletics. Ruby is hawking two tickets on the third base line for $50 each (the regular price is $10.50). The game has already started, and Jack can hear the roar of the crowd inside the stadium. He is getting desperate to unload the tickets. Two other ticket scalpers are working nearby. Ruby finally gets a buyer and is about to sell his tickets when the two rival scalpers run over and offer similar tickets for less money. Ruby is furious. Even though it’s two against one, Ruby sucker punches one of the scalpers. When the scalper’s buddy tries to help, Ruby takes out a pair of brass knuckles and proceeds to beat both men to a bloody pulp in a fit of rage. He grabs the money from the rival scalpers and runs off down the street just before the police show up.

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Jack has an altercation with rival ticket scalpers during the 1929 World Series at Wrigley field. He uses brass knuckles to severely beat his two rivals.

Jack is sometimes called “Sparky” by those close to him. According to his sister, Eva Grant, the nickname comes from the way Jack wobbles when he walks, resembling the slow-moving horse named “Sparky” in a contemporary comic strip. Eva says that her brother hates being called “Sparky” and that he’ll punch out anyone calling him that. Some of his acquaintances think Ruby is called “Sparky” because of his quick temper.

Ruby Moves to California.

The nation is still mired in the Great Depression, and jobs are hard to find. So Ruby does what so many other Midwesterners do. He packs up and moves to California. Sometime in 1933, Jack and several friends head west. They first go to Los Angeles. Unable to find steady employment, they resort to selling racing tip sheets for the new Santa Anita Racetrack that has just opened. It turns out to be less lucrative than they hoped, so Jack takes a job as a singing waiter at an Italian restaurant. He earns even less money at that job.

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Jack moves to Los Angeles to find work and ends up selling tip sheets for the Santa Anita Racetrack.

After a year of struggling to make a living in Los Angeles, Jack moves to San Francisco in hopes of finding better opportunities. He continues selling racing tip sheets, this time at the Bay Meadows Racetrack. He also takes a job selling newspaper subscriptions door-to-door. He is moderately successful at this endeavor and eventually becomes a crew chief managing several dozen salesmen.

In June, 1934, Jack’s sister, Eva, moves to San Francisco. She brings Ronald, her son from a previous marriage. Jack gets Eva a job selling newspaper subscriptions. A short while later, Eva meets and marries Frank Grant, and the four of them share an apartment for a brief period.

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Jack moves to San Francisco in 1934 and sells newspaper subscriptions door-to-door.

After Eva’s family moves out, Jack takes in a couple of roommates. They all seem to get along well. His roommates describe Ruby as nice and personable. Ruby seems to have a normal social life. He hangs out with a sports crowd, mainly boxing enthusiasts. He also has great interest in police work and often says that, if he were tall enough, he would like to be a policeman. All his friends know him as “Sparky.” Apparently, he has outgrown his disdain for the nickname, and now even seems to embrace it.

In San Francisco, Ruby does well in newspaper subscription sales. The subscription manager describes Ruby as “an honest, forthright person.” His co-workers say that he is a well-mannered, likable individual who is soft spoken and meticulous in his dress and appearance.

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Jack does well in newspaper subscription sales in San Francisco.

Sometime in 1936, Ruby meets a young girl named Virginia Belasco, who is the granddaughter of a prominent playwright and actor, David Belasco. They meet at a dance at the Jewish community center in San Francisco. Although they see each other socially off and on for the next few years, the relationship doesn’t blossom romantically.

During that same time, however, Jack meets another woman named Virginia Fitzgerald that he gets very serious about. He wants to marry her, but she is not interested. Ruby is so devastated by the rejection that he packs up and returns to Chicago in 1937.

Back on the Streets of Chicago

Following his return to Chicago, Ruby is unemployed for nearly six months. Somehow, though, he is able to maintain a normal existence without getting financial assistance from his family or friends. Occasionally, he has to resort to dining at a soup kitchen. Out of necessity, he reverts to his street ways, scalping tickets and buying watches and other small items for resale at discount prices. One of his closest Chicago friends thinks Ruby’s sales and promotions are “a little shady but legitimate.”

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Once in a while, Jack has to go to a soup kitchen for a bite to eat.

Then Ruby gets a break. He makes friends with a young attorney named Leon Cooke, the financial secretary for Local 20467 of the Scrap Iron and Junk Handlers Union. Cooke and Ruby become best buddies. Cooke ends up hiring Ruby to work for the union in December, 1937. His title is “union organizer,” but in actuality he is really the muscle for Cooke. You sometimes have to push your weight around when you’re dealing with union issues. Cooke is a lawyer whose role is to raise worker wages to a reasonable level.

Everything goes well for Ruby for the next couple of years until the mob moves in. John Martin, the Chicago District Clerk for Sanitation, with the backing of mobster Murray “Mr. Einstein” Humphreys, takes control of the union. Humphreys is the brains behind the Chicago syndicate’s move to take over the city’s labor unions. Cooke now works for Martin and Humphreys, and so does Ruby. He becomes the bag man, collecting and delivering payments for the Junk Handlers Union and the mob.

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Murray “Mr. Einstein” Humphreys (L) is the brains behind the Chicago mob’s move to take over labor unions in the 1930s. Humphreys and his wife Jeanne are shown years later.

On December 8, 1939, Cooke gets into an altercation with Martin over a financial issue involving union pay rates. The argument turns physical and Martin shoots Cooke three times in the back. Martin takes the office secretary hostage and makes a getaway. At first, Jack Ruby is suspected as an accomplice and is picked up and questioned by police. A short while later, Martin releases the secretary and turns himself in, claiming self-defense. Martin is released by the District Attorney, even though circumstances clearly show it wasn’t self-defense.

Ruby is released shortly after Martin’s arrest. Within days after the murder, Tubbo Gilbert, the Cook County (Illinois) chief investigator, confiscates all relevant paperwork from the union and all police records about the shooting. All the notes and records about the death of Leon Cooke mysteriously disappear, never to be found.

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In 1939, Ruby is arrested as an accomplice in the murder of Leon Cooke. He is working for Murray Humphrey at the time. He is questioned and released without being charged, and all records of the arrest disappear.

(A strange event occurs in the late 1950s when Robert Kennedy tries to investigate Jack Ruby’s role in the Cooke shooting. At the time, Kennedy is serving as chief counsel for the Senate Select Committee on Improper Activities of Labor Unions and Management, better known as the McClellan Committee. Robert Kennedy realizes that he will never get to the bottom of the Ruby story, and gives up his investigation. The fact that Jack Ruby is on Robert Kennedy’s radar several years before the assassination of JFK is a bit curious, especially when Ruby is later portrayed as just some schmuck who owns a strip joint in Dallas.)

Cooke dies of gunshot wounds on January 5, 1940. Ruby is deeply saddened by the death of his good friend, so much so that he later changes his middle name to Leon to honor Cooke’s memory.

Martin is replaced by Paul Dorfman, a big-time Mafia labor racketeer. After Dorfman takes over, the AFL-CIO calls the Waste Handlers Union “basically a shake-down operation.” Ruby stays on as bag man for Dorfman until the end of January, 1940, then falls in with Benny Zuckerman, a mobster who works under Lawrence “Dago” Mangano. Mangano is planning a move on Chicago mob boss Paul Ricca to take over the gambling rackets. However, Ricca learns of Mangano’s plan and, in a surprise attack, guns down both Mangano and Zuckerman. Some believe it was Jack Ruby who tipped off Ricca.