Owney Madden was born on December 18, 1891 in Leeds, Yorkshire in England. His father worked on the docks, but moved the family to the United States in 1903. They eventually settled in New York City's "Hell's Kitchen" neighborhood.

At a young age, Owney and his brother joined a group of hoodlums known as the Gopher Gang. He quickly developed a reputation for his fighting skills during battles with rival gangs. Over time, he became a leader in the gang and was soon making about $200 a day from the gang's criminal activities.

In 1910, he shot and killed a man who had asked out one of his many girlfriends. The man was named William Henshaw and he later died of the wounds, but not before identifying Owney as the attacker to police. However, Owney was able to get himself acquitted of charges after threatening all of the twelve witnesses before the trial.

On November 6, 1912, Owney was leaving the Arbor Dance Hall in a drunken state when several members of a rival gang, the Hudson Dusters, approached him. They shot him eight times, but he managed to survive. After leaving the hospital, six members of the gang turned up dead, but there was no evidence linking the crimes to Owney.

In late 1914, Owney became involved in a dispute with a man name Patsy Doyle, a member of the Hudson Dusters. Owney had gotten involved with one of Doyle's girlfriends and Doyle took revenge by informing police of many of Owney's criminal actions. Doyle took things even further by attacking one of Owney's friends, Tony Romanello. On November 28, 1914, Owney ambushed Doyle and shot him dead.

The police were able to pin the murder on Owney and he was sentenced to twenty years in prison. He spent the next nine years serving time at Sing Sing Prison before he was released on parole in 1923.

After returning to his neighborhood, Owney found out that the Gopher Gang had been broken up in pursuit of bootlegging ventures. He eventually landed a job working for a taxi company as a strike breaker. He was very unhappy with his pay, however, and sought criminal work once again. He was hired by Dutch Schultz and helped fight Schultz's bootlegging opponents.

After a short time, he opened a popular night club known as the "Cotton Club". He was also able to open laundry facilities and coal delivery businesses citywide. In 1931, he joined a group of boxing promoters to fund the careers of Max Baer, Rocky Marciano, and Primo Carnera. He spent much of his time arranging fights, but also directly managed Primo Carnera.

In 1932, Vincent Mad Dog Coll tried to blackmail Owney, but he was killed by a drive by shooting. Owney was arrested for violating his parole that same year and began shifting himself away from criminal activity.

In 1935, he decided to move to Hot Springs, Arkansas, where he was able to open the Hotel Arkansas. The hotel was a spa and a casino that became popular as a hideout for mobsters. In 1943, Owney became an official United States citizen and married a woman that lived in town. On April 24, 1965, he died from natural causes.