Owen Vincent Madden was born December 18, 1891 – although his tombstone records his birth as December 25 – to Francis and Mary Madden in Leeds, England. The discrepancy between these dates is a reflection of Madden's desire to not want any celebration or limelight cast upon himself, according to Billy Wells, Madden's long-time light duty man. Wells, in a 2009 interview with screen writer and executive director of The Gangster Museum of America, Robert Raines, stated, “Owney didn't want no attention. He didn't want anyone making a fuss over him. He always said his birthday was on Christmas, so that no one would celebrate him." Wells said that he was very private, but very generous with his money. And plenty of money he had. Years of prohibition liquor revenue from The Phoenix Cereal Beverage Company and the ownership of New York businesses, the Stork Club and the Cotton Club, left Madden with considerable wealth. Madden served a second but short term at Sing Sing for a parole violation, and upon his release was informed that he was no longer welcome in the State of New York, by powerful politicians, federal prosecutor Thomas Dewey, Mayor Fiorello LaGuardia, and then New York Governor, Franklin Roosevelt. Thus he decided to move his fortune and apply his organizational skills to a small valley town in Arkansas with a very large, and soon to be, larger illegal gambling operation.
His old acquaintances from Hell's Kitchen, Meyer Lansky, Lucky Luciano, Ben Siegel, Dutch Schultz and even his Sing Sing warden, Lewis Lawes would visit him regularly for advice, and in turn, Madden would be able to catch up on his beloved city, New York. Norwood Phillips, a well-respected attorney and native of Hot Springs, considered Madden to be the most generous wealthy man he had ever known. Madden's generosity had an impact on the youth of the community – by virtue of the largest Boys Club constructed in the State of Arkansas at that time – and in the purchase of uniforms for the High School band, among whose members included former President Bill Clinton, according to Phillips. “His passion to help the less fortunate, such as churches and community organizations was unbelievable and mostly anonymous," said Phillips. This passion even extended to the many pets he had (now buried around his former home at 506 West Grand) and the homing pigeons that he loved to utilize as couriers of cryptic messages between himself and New York mobsters. However, he never relinquished his toughness and his ability to strong arm a situation if needed, according to Billy Wells. This fact was well known by even his friends, as Mae West once quoted that Madden was “sweet, but oh, so vicious." Meyer Lansky considered Madden the toughest man he knew, and he knew plenty of tough men.