• Choose a category
• All
• Classic-Fiction

By Root 944 0

Roache during the gang war. Buddy, whose brother Mickey later became Boston’s police commissioner, ended up crippled and in a wheelchair. In March 1971, not too long after he shot the wrong McGonigle, Jimmy went to New York to pick up guns. Before he left, he told Billy to be careful while he was gone and not to drink. But that night, Billy hung around with Kevin O’Neil down at the Transit Café and ended up drunk. Kevin offered him a ride home, but Billy refused the offer. Heading home, he was chased by a couple of men with the Mullins gang who caught up with him when he tripped on a manhole cover about 200 yards from his house and fell down. While he was lying there, his pursuers shot him to death. If Kevin O’Neil had ended up driving Billy O’Sullivan home that night, he probably would have been killed, too.

The reason for Richie Castucci’s murder five years later wasn’t any more difficult to understand. A bookmaker, Castucci had been cooperating with the FBI about the Winter Hill gang and bookmaking, shakedowns, and murder. He was also giving information as to the whereabouts of certain members of Winter Hill who were on the lam. Once FBI agent John Connolly informed Jimmy about Castucci’s cooperation, Winter Hill put in a bunch of bets with the bookmaker. If they lost, Castucci wasn’t getting his money because they were going to kill him. If they won, they would collect the money off Castucci and still kill him. As it was, they lost the bets. A meeting was set up for Castucci to come over and collect the money. When Castucci came over to meet Jimmy and Stevie and Johnny Martorano, Jimmy and Stevie gave him a bag of money and told him to go to the house around the corner to count the money. While Castucci was sitting at the kitchen table counting the money with Jimmy and Stevie, Johnny came in and shot him in the head. They put Castucci’s body in a sleeping bag, which made it easier to move him, and deposited it in the trunk of his Cadillac. An associate who had some involvement in the murder actually wanted to be reimbursed for the $17 he had laid out to buy the sleeping bag!

Jimmy O’Toole, a well-known gangland figure involved in armored car robberies, had been aligned with members of the Charlestown-based McLaughlin gang. His murder in December 1973 was hastened by Eddie Connors, who alerted members of Winter Hill that O’Toole was leaving the Bulldogs Tavern on Savin Hill Avenue. Jimmy O’Toole hadn’t gone far down Savin Hill and Dorchester avenues when four Winter Hill cars surrounded him, two to block off the ends of the street so no one could get in or out, one to act as a crash car in case the police arrived, and the fourth to serve as a hit car. O’Toole ducked behind a mailbox, which was on a cement pad, not attached to the ground. He kept moving the mailbox from side to side to keep it between himself and the bullets which poured out of the cars. Finally, Joe MacDonald got frustrated and jumped out of the car, walked up to O’Toole, and shot him in the head. Although he was in one of the four cars, Jimmy didn’t fire the fatal shot that night. I believe the murder was more payback for O’Toole’s involvement in the shooting of Stevie’s brother, the Bear, when O’Toole was hooked up with the McLaughlins, than for anything else. The Bear had been hit eleven times but survived.

Eddie Connors, who also had a hand in the rackets, died less than three years later. After he was arrested for a $500,000 armored car robbery, Jimmy and Stevie were worried he wouldn’t stand up and might be cooperating with law enforcement. They thought he was starting to talk about his part in the O’Toole murder.

On the night of June 12, 1975, members of Winter Hill sent a message to Connors to give them the number of a pay phone where they could call him. Connors gave the number of a phone booth outside a Sunoco station across from Orbit’s department store in Dorchester. He then parked his Lincoln Continental with the motor running and walked over to the booth to await the call. Waiting in the weeds outside the telephone booth on Morrissey