Three days later the Touhys lined up three of Nitti's men and shot them through the knees with machine guns after they tried to muscle into a meeting at the Chicago house painters' union.
The Touhys scored another big hit when they killed Danny Cain, the thirty-two-year-old president of the Chicago Coal Teamsters and brother-in-law of George Red Barker. Several men in a car followed Cain home as he left a nightclub. They pulled up alongside his car and drowned it in machine gun fire.
On a freezing Wednesday night, Willie O'Brien, a slugger employed by the Touhys, walked into a popular speakeasy called the Garage. There he was jumped by three men who tried to force him outside to the rear alley where a car was waiting. O'Brien managed to fight them all off until one of the men pulled a pistol and fired a shot into O'Brien's back. Unarmed, O'Brien was running toward the front door when another shot caught him in the leg and a third shot went into the palm of his right hand as he used it to cover his spine. A half an hour later O'Brien staggered into the waiting room of the Augustana hospital.
Officer Martin O'Malley, who grew up with Touhy and O'Brien in the Valley, arrived and interviewed the hood on his death bed.
'Who shot you Billy?"
"I known them. Known them for ten years, but I won't tell you who they are. "
"You're going to die Billy. Who killed you? I'll have your revenge."
O'Brien just shook his head and died.
Seven days later, the Touhys struck back. It was fifteen degrees below zero and snowing when a car pulled up to the curb. Several men in long coats climbed out, walked into a pool room and poured five shots into a syndicate hood named Fred Petilli who was leaning against a pool table, his back to the door. A few moments later the same car pulled up in front of The Garage nightclub where Jimmy O'Brien had been killed. A tall man, probably Basil Banghart, opened the front door to the club, tossed in a bomb and said "This is for Jimmy, you bastards!"
The bomb blew the place to bits but remarkably, no one was killed.
After that, Charlie O'Neill, a very young Touhy gunman, was kidnapped off the street, shot twice in the head and dumped in the middle of traffic on a busy intersection.
The Touhys responded by killing a labor goon named Nichols Razes. They shot him five times during a running gun battle in the Green Hut restaurant owned by Razes' brother. Charles McKenna, a Touhy labor enforcer and president of the truck painters' union, was shot in the arm during the gun battle. He was arrested for murder as he straggled down the street, murder weapon still in hand. He was held, booked and then released for "lack of evidence."
That same month, the syndicate tried to kidnap Roger Touhy's two sons as they waited for their mother to pick them up from school in Des Plains. Somebody had to pay for that and Roger chose Eddie Gambino, a dope peddler and union goon. They caught Gambino as he was about to step out of his car. Two gunmen, stepped up to the driver's window and opened fire. Before he bled to death, Gambino was able to pull his own pistol but dropped it before he could fire at his killers. One of the two killers, enraged at Gambino's defiance, stepped back over to the hood's blood-smeared face and fired at his temple.