Chicago has almost always been considered a loose place, a breeding ground for colorful characters and stories straight out of a Damon Runyon novel. In the early 20th century, Al Capone and the Black Sox scandal embodied the culture of gangland Chicago: anything goes.
On the far west side of town, the North Lawndale area known as the Maxwell Street Ghetto became the Jewish enclave in the 1910s and 1920s. Don't think, though, that the term "Jewish" meant that the children living in the Old West Side lived up to the standard "genteel and studious" stereotypes. Even though the old Route 66 -- the one about which the famous song was written -- went through North Lawndale (Ogden Avenue) on its way to Santa Monica, Calif., the hardscrabble immigrants living there didn't exactly have an easy path to better lives.
"They all came out of this rough-and-tumble world that produced boxers, judges and gangsters," said Douglas Century, author of "Barney Ross: The Life of a Jewish Fighter." "They absolutely had the same values -- they believed fervently in Jewish self-defense."
Jacob Rubenstein knew all about surviving. The son of Polish Jewish immigrants, Rubenstein loved boxing, and at a downtown gym, he eventually met another second-generation Jew, an aspiring fighter named Dov-Ber Rasofsky.
When Dov-Ber (slightly Americanized to Beryl) was 14, his father, a grocery store owner, had been shot dead in his store by two robbers. In need of money to train, Rasofsky was helped out by the legendary Mafioso himself, Capone, and his associates, including "Tough Tony" Capezio and "Machine Gun Sam" Hunt. They bankrolled more of Rasofsky's budding boxing career.
Rubenstein attended many of his friend's fights. By then, Rasofsky went by the name Barney Ross so that his family wouldn't find out about his boxing career. Rubenstein and Ross shared a simpatico based on more than just their Jewish heritage. Both of their mothers had suffered nervous breakdowns. Rubenstein had been through the foster care system, as had three of Ross' siblings. They wondered why the god for whom their parents had suffered so greatly would allow such depravity and tragedy to befall their families. They became disillusioned.
Rubenstein stayed close to Ross as the latter carved out one of the greatest boxing careers of all time. He won world championships in three different weight classes, becoming the first boxer in the Queensbury Rules era to win championships in two weight classes simultaneously. Barney Ross retired with a record of 72-4-3, with 22 wins by knockout. He's now enshrined in the sport's Hall of Fame.
During his nine-year pro career, Ross was never knocked out despite having faced some of the era's best pound-for-pound fighters. He edged lightweight and junior lightweight champ Tony Canzoneri twice and took two out of three slugfest decisions from welterweight champ "Baby Face" Jimmy McLarnin.
Both Ross and Rubenstein would enter the military in their early 30s to fight in World War II. Ross, a Marine, became a hero for valiant fighting during the Battle of Guadalcanal. He had survived the August 1942 sinking of a torpedo boat, PT-109, whose commander was a certain Lt. John F. Kennedy. Rubenstein served in the Army Air Forces, earning a sharpshooter rating for superior marksmanship. Therein lies the main difference between Barney Ross and his childhood friend, Jacob Rubenstein. Ross' legacy -- boxing legend and war hero -- would become forever sepia-toned. His childhood friend would soon be considered one of the most infamous men in American history.
When the war ended, Rubenstein and Ross continued to hang out at the North Lawndale pool room owned by Davey "Yiddles" Miller. Their lives continued to parallel even as they grew apart. Barney Ross moved to New York and worked at an advertising agency. Jacob Rubenstein moved to Dallas and changed his name, as his friend had, to Jack Ruby. Proving that you can take the boy out of the street but not the other way around, Ruby became a strip-club owner.
They were each accused of running weapons to other countries -- Ross to the newly formed state of Israel, and Ruby to Cuba. Ruby was rumored to have mob connections, most concretely described by Bill Bonanno, the son of New York mafia boss Joseph Bonanno, in his memoir, "Bound By Honor: A Mafioso's Story." Bonanno linked Ruby to Mafia-led forces opposing Cuban dictator Fidel Castro.
Ruby's family said in recent years that he had been fiercely loyal to President Kennedy, supporting the way Kennedy handled the Cuban Missile Crisis of 1962. A year later, on Friday, Nov. 22, 1963, Ruby took special notice of an anti-Kennedy advertisement in a traditionally Republican-leaning newspaper, the Dallas Morning News. When JFK was assassinated later that afternoon while riding in an open motorcade through the city, Ruby saw a potential connection. Perhaps feeling the slight gravitational pull of the Jewish heritage he shared with Barney Ross, Ruby thought that the ad -- the work of a right-wing activist named Bernard Weissman -- would make readers deduce that Jews had killed JFK.
Despite (or perhaps because) Ruby owned a strip club, he became quite friendly with members of the Dallas police department. One of Ruby's workers, Nancy Perrin Rich, later testified to the Warren Commission that Ruby used to supply free drinks to police officers. "I don't think there is a cop in Dallas that doesn't know Jack Ruby. He practically lived at that [police] station. They lived in his place."
Following the assassination, Ruby actually provided what might be called moral support for the now-overwhelmed Dallas police. He bought them sandwiches and visited the police station on the day following the shooting. On Sunday, Nov. 24, 1963, Ruby and his roommate, George Senator, rose at 4:30 a.m. and took photos of a roadside billboard that resembled the anti-Kennedy ad he had seen in the Dallas Morning News. This one read "Impeach Earl Warren," referring to the Chief Justice of the Supreme Court and, eventually, the head of the special seven-man commission investigating Kennedy's assassination.
Later that morning, Ruby wired $25 to one of the strippers at the Carousel Club, Karen Carlin. That was at 11:17 a.m. CT. Four minutes later, at 11:21 a.m., Jack Ruby walked into the police station in downtown Dallas -- his version of "Cheers," where everybody knew his name -- just as police were transferring suspected JFK assailant Lee Harvey Oswald to a downtown jail. Ruby moved quickly through the crowd and, on live television, used a .38 Colt Cobra to shoot Oswald, fatally, once in the stomach.
In an era when events didn't move as quickly as our Internet-driven society does today, two FBI agents tracked down Ruby's old friend, Ross, within 24 hours of the incident. According to author Douglas Century, the FBI wasn't worried about connecting Ruby to the Italian mob. The feds worried about his associations with infamous Jewish gangsters Lenny Patrick and Dave Yaras, who for several decades ran Chicago gambling on the far north side of the city. The Jewish mob guys remained huge fans of their local ethnic hero made good, Barney Ross. Was it possible that Patrick and/or Yaras sent Ruby to Dallas to do their bidding?
Ross spoke several times to government authorities about Ruby, even testifying as a character witness on Ruby's behalf before the Warren Commission. Ross essentially said that Ruby was nuts, muttering something about Sparky (the neighborhood nickname for Ruby, owing to his notoriously short temper) being too tough to control. Author Douglas Century told of a story that Ross' brother, George, recounted about a trip to a Chicago Bears game when another fan blocked Ruby's car in the parking lot. Ruby flew into a rage, George Ross remembered, and pummeled the other driver.
The Warren Commission Report further states, "When, during an argument, an [Army] sergeant called Ruby a 'Jew Bastard,' Ruby reportedly attacked him and beat him with his fists." In essence, few believe Ruby could have been a mob "patsy" -- someone set up to take the fall -- because he was an unstable character, not someone the mob could control.
Ruby was convicted of murder in 1964, though two years later his death sentence was reversed. It made little difference, because Ruby died of cancer on Jan. 3, 1967, at the same hospital -- Parkland -- where President John F. Kennedy had been pronounced dead just more than three years earlier.
In a final parallel to their lives, Ross also died of cancer, just two weeks after Ruby, on Jan. 17, 1967. It could be said that Ross died in a prison of his own: He couldn't outrun his narcotics addiction, his body craving heroin ever since he was given morphine to ease the pain at Guadalcanal. While some of the most noteworthy events in Ross' life carried a degree of finality to them -- a boxing knockout leaves little to the imagination or conspiracy theorists -- Ruby's mystery traveled with him to his grave.
Ruby insisted in his final years that he was involved in a conspiracy, which the Warren Commission report denied but which the House Subcommittee on Assassinations asserted. Some of those HSA documents were published, but most of the files remain locked away until 2029. Half a century after the fact, Jack Ruby remains one of the great twists on the quintessential American story: hardscrabble immigrant, defender of the nation, successful businessman ... and assassin.