§15: Re-Examining Whitey Bulger: The Learning Years: The Boys Who Live On The Hill

Whitey May Have Considered
This As A Hideout

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.


  1. The media created the “Whitey” myth and the government continued it when Bulger was outed as an informant and it was learned that the Boston FBI were partners with Bulger and Flemmi.

    Bulger is a smart ruthless criminal but in no way the so called Mob boss mastermind he was portrayed as. Bulger ran Southie and that was it. Flemmi, the LCN favorite, partnered with Bulger but ran the South End and Roxbury independent of Bulger.

    The original indictment targeted Bulger, Flemmi and Salemme with others showing a RICO involving Winter Hill and the Mafia working in concert which they were but Bulger wasn’t in charge or even a rival he just ran Southie and paid the Mafia for the opportunity to do it.

    The government has to make whoever they target the biggest and baddest criminals around like all the so called terrorists that have bee indicted on fake entrapment cases and sent off to prison but in reality most of them were harmless wannabees duped into conspiracies.

    Bulger will spend the rest of his life in prison, whether the federal Supermax or Plymouth County. He knows it but meanwhile he’ll make the governemnt squirm.

    The case against him shows his intelligence and toughness; while rotting away in jail he’s keeping powerful people, all the way to the head of the FBI, up worrying at night.

    Pretty good for a guy from the Southie projects.

    • Notoboyo:
      You nailed everything especially your comment “Pretty good for a guy from the Southie projects.” You know what most amazes me about the whole situation surrounding Whitey is that much of what the public and the judges believe comes from the mouths of the gangsters who are incapable of telling the truth. Imagine believing Flemmi and making findings of fact on what he says. The naivete of these people is astounding when you think these gangsters knew they could get a good deal if they made Whitey the boss and most evil person, in fact, the worse they made him the better the deal. It was like giving bananas to monkeys, they couldn’t make up enough good stories about him once his FBI protection fell through.
      You are right about how the government acts. It doesn’t apprehend the real criminals because they are on the FBI’s payroll. It hires the real ones to line up what you call the harmless wannabees and gives them the explosives which they could never get themselves and then arrests them before they explode them. You are also right about the balance of power among the criminals. It’s good to hear from you again.

  2. I also would like to add, based upon my experience in growing up amongst peers who would go on to recieve convictions for murders, that having murders under your belt doesnt mean much in a one on one situation or relationship with someone that has a history of coexisting with convicted violent felons, including murderers. It is not like Whitey was unfamiliar with the type of mindset those in Winter Hill had, in fact, i argue that he had a pretty good idea of who he was dealing with.

    • John:
      Growing up with those guys you knew they all had similar things but also very different things about them. Each one had to be treated as an individual with a touch of respect. The Winter Hill gang were pretty much like any other group of murderers. Whitey would have a good sense of what he was getting involve with and would know enough not to trust any one of them until after a while. He really did not know much about them. He’d treat each one differently but he had supreme confidence in his ability to figure out what made them tick and how to use each one to his greatest advantage. He’d end up partnering with the worst of the bunch who was Stevie Flemmi. He dealt with Martorano using Flemmi as a go between. He was not unaware of his peril and his advantages and kept on the good side of Howie until he eliminated his opposition in Southie and Howie got sentenced. But during it all he maintained his distance while giving none of them a reason to distrust him.

  3. Whitey shows us, through your much nuanced evaluation, the power of patience, perception and ability to make a sucessful late run in a highly competative field. The fact that he obstained from drugs and alcohol,was dedicated and methodical throughout his criminal career, had a highly intelligent and dedicated younger brother to keep up with, did hard time with the worst of the worst, all seemed to set him apart from the pack, however murderous they were.I think he especially stood out in the Southie scene, not at the time so much, but in retrospect. Based upon multiple accounts of meetings with Whitey, from Robert Fitzpatrick, Pat Nee or those outlined by Kevin Weeks, Whitey was keenly aware of the posturing, presentation, and the need to perpetuate a lengendary reputation amongst his contemporaries. He certainly was not the most ruthless…maybe the most cunning

    • John:
      Thanks for the comment. There is nothing that you wrote that I disagree with and wish I could have put it a succinctly as you did. Whitey seemed to look at the big picture and planned for a long run; the others were day-to-day guys. He was clearly the most cunning.