Some will suggest Whitey was the toughest guy around so just being near him caused the others to respect him. Yeah, it’s good to be seen as tough and Whitey had all those attributes that would endear him to the gangsters except their trust. That’d have to be earned and that meant time. As far as his toughness making him able to intimidate these gangsters, keep in mind the weakest guy with a gun will beat the toughest guy without one any time. All of Whitey’s future partners carried, all of them were murderers, and none would have hesitated to take Whitey out in a moment’s notice if he came to Winter Hill and tried to take over.
It seems to me that throughout 1973 and up until at least May 1974 Whitey was just a hang around guy who came around every once in a while to touch base and pay his dues to ensure his protection was still there. Whitey had Southie on his mind. He had made peace at home but it was fragile. Some big Mullen guns were still lurking there who figured they sold out short and would like to take over the whole operation.
Martorano notes: “Whitey Bulger was the only original partner who didn’t have ties to Somerville, but he, too, quickly began spending at least a few hours at the garage every weekday.” It is true that Whitey didn’t have the Somerville ties which again shows he had big obstacles to overcome before having a leadership position. I’d suggest initially he was more circumspect in his appearances at the Marshall Motors garage than Murderman now suggests and it was a while before he spent much time there.
It’s important to understand that Whitey himself would not be inclined to jump into the laps of guys he did not know. He’d feel his way in. That takes time and space. What must have taken a couple of years is condensed into a couple of hours by some people. Gangsters don’t have kumbaya moments.
AUSA Jeremiah O’Sullivan the head of the Federal Strike Force in Boston said all the Winter Hill Gang were murderers. He broke it into two groups. He insisted there were a Winter Group, consisting of Howie Winter, Joe McDonald and Jimmy Sims, and a Winter Hill Gang which included the Winter Group and the Martorano brothers, Whitey and Stevie Flemmi. If O’Sullivan wanted to use that type reasoning then to be absolutely correct he should have said there were a Winter Group, a Roxbury Group, and one other person, Whitey, who eventually made up the leadership of the Winter Hill Gang.
When people talk about this time, few seem to focus on the Roxbury Group. This was a close-knit group of really bad killers, much worse than any group that ever existed in the Eastern Massachusetts area. They were involved in the big Irish gang war even though they were all Italians and one Jew. As Italians they were trusted by the Mafia and did contract murders for them. This group consisted of Stevie and Vincent “Jimmy the Bear” Flemmi, John and Jimmy Martorano, Frankie Salemme and George Kaufman.
Two, Jimmy the Bear and Kaufman are now dead; two Jimmy Martorano and Frank Salemme, are alleged to be made members of the Mafia; the two Flemmis were federal stooges; Kaufman was a trusted associate who was a facilitator but not involved in the murders, as best I can tell.
Even within this small group friendships differed. Flemmi and Salemme went way back and were close to the Mafia’s Larry Baione; the Martorano brothers were like two peas in a pod; Kaufman was closest with Salemme. After Salemme did his 16 years in prison he’d again hook up with and do business with Stevie Flemmi to Whitey’s great displeasure. Old habits die hard.
Whitey was faced with dealing with these guys with long past associations whose loyalties ran in many different directions. He’d know some were connected with the North End, another term for Gerry Anguilo’s Mafia group. Larry Baione had a reputation throughout Boston that equaled any Whitey would ever achieve. He was the enforcer for the Boston Mafia.
Whitey would know the Italians of the North End and the Irish of Southie never got along that well and were wary of each other. He’d know of the trap that they set back during Prohibition when they invited a couple of the Gustin gang to meet in the North End and eradicated them. He’d know how easily they could make him history. Whitey, too, wanted to be sure of his back as much as the other gangsters he was befriending. He would have gingerly made his way into the confidence of the boys on Winter Hill.