Bill Brennan was an ex-boxer who fought his last fight on November 7, 1923. In one hundred and twenty one bouts he racked up sixty-five knockouts while only being KOed four times himself. His shining moment in the ring was on December 14, 1920 when he managed to go twelve rounds with Jack Dempsey.
Retired from the ring by 1924, the thirty-one year old former pugilist and family man -he had a wife and three and half year old daughter- opened a speakeasy on the second floor of a two-story building called the Club Tia Juana.
Around 4:30 am on this date eighty-six years ago Bill was sitting with his sister Shirley and a friend named James Cullen, who was a state trooper stationed in White Plains, while the club's staff was cleaning up. A man came in an tapped Bill on the shoulder saying, “Bill can I see you a minute?” As a celebrity of sorts Brennan was used to people approaching him so he said, “Certainly.” The two men stepped into the hall way and before there was a chance to speak two shots rang out and Brennan let out a scream and fell face down with bullets in the chest and stomach.
Hearing the shots, Shirley and Cullen ran into the hallway and saw two men running for the staircase. Shirley grabbed one of them by the sleeve but he knocked her down and fired a shot that missed. Another shot was fired at Cullen, which went through his neck. He managed to chase the men about another twenty feet before collapsing.
Shirley ran back to her brother who said, “I’m dying Shirley.” “For God’s sake, Bill, you’re not!” she cried back. “My poor wife, my poor child! Poor Mary.(his wife)” He continued. Shirley tried to roll him over but the pain was to great so he remained face down. Seeing that he was about to die Shirley asked him, “Do you know who they were Bill?” “I don’t” he replied, before going unconscious. He died before he could be placed in an ambulance.
After the shooting the two gunmen ran down the stairs and found the door locked so they busted through the glass with the butts of their guns. Hearing the shattering glass, Police Lieutenant John Haggerty figured robbers were at work and ran to the scene and grabbed both the gunmen but they beat him with their pistols. They knocked the officer to the ground and kicked and stomped him until he was unconscious then, waving their pistols, they jumped on the running boards of a car containing three men who were leaving town on a fishing trip.
They forced the driver to speed away. A taxi driver who witnessed the getaway hollered to a cop who was arriving on the scene and told him to jump in and they pursued the getaway car. After a short chase the taxi crowded the getaway car to the curb and the officer jumped out and captured the gunmen who had since thrown away their guns.
The gunmen were Joe “Babe” Pioli, twenty-seven, and Terry O'Neill, thirty-one (also an ex-fighter). The men were “questioned” at the High Bridge police station before being transferred to police head quarters. When they showed up at headquarters they were so badly bruised that a doctor was called in to treat them. The police explained that the men had fallen down while leaving the station.
Both men had records and Pioli was known to be a bootlegger. That plus the fact that a barrel filled with empty whiskey bottles in the Club Tia Juana led police to believe that the shooting was a bootlegging quarrel.
Years later it would be said that Brennan was killed over a bootlegging debt owed to Legs Diamond but Pioli was a long time whackadoo who had gotten into a skuffle with Brennan earlier in the evening and came back later to get even.