Howie Winter – The Leader of a Gang That Did Not Exist

So we hear of the death of Howie Winter at age 91 who was born in 1929 and allegedly enlisted in the Marines at age 14 to fight in WWII.  I suppose it was possible to do at that age since there are reports of some kids doing it (one as young as 12) but all gangster histories I take with a grain of salt.

Again we hear about the Winter Hill Gang and the Irish Gang Wars – all a lot of nothing but made into something by our local media.

There were two Irish Gang Wars in the 1960s and 1970s. The total deaths from the McLaughlin (Charlestown) against the McLean (Somerville) was 3; the total from the South Boston war, the Killeens against the Mullins also totaled 3.  There were over 100 gangsters murders during this time. They are all lumped under “Irish” even though most were “Italian.”

There were more McLaughlin gang deaths but that was because they got involved in a fight with the Italian Roxbury gang when they went after Jimmy Flemmi. That was an Italian against the Irish war in which the Irish McLaughlin gang was decimated.

The Winter Hill Gang really never existed. There were a group of guys who were bookies and tailgaters and strong arm men who hung around. Each has his own business and they shared in some things together. It corrupted no legitimate people, had no judges or elected officials on its payroll; and only had one or two cops it compromised.

The involvement of Howie Winter started out with his friendship with Buddy McLean another thief and legitimate tough guy.  Long story short: Buddy beats up George McLaughlin in September 1961; McLaughlins try to blow up his car; he and Alexander Petricone, Jr. (Alex Rocco) are said to have killed Bernie McLaughlin in October 1961;  Petricone and Buddy go to jail for beating up a guy;  Petricone’s wife borrowed Howie’s car in September 1962 to go shopping and it blows up as she’s driving it (Flemmi had nothing to do with it. ) Things quiet down. Edward McLaughlin murdered October 1965; Buddy murdered a week or so later. Howie left standing with his buddies, Sal Sperlinga, Joe McDonald and Jimmy Sims. The feds call them the Winter gang engaged in bank robberies, hijackings and gambling.

In 1972 Whitey Bulger needing protection joins Howie Winter with John Martorano. Two years later Steve Flemmi joins. They hang around in a garage on Winter Hill in Somerville. Gang then named after that location (not Howie).

According to Martorano Jerry Angiulo local Mafia head hired Howie and Matorano (who had Mafia guy connections) to kill Al Angeli and others in his gang because they murdered Paulie Folino who ran Jerry’s Watertown and vicinity gambling business. Sims driving, Howie and Martorano firing, they murder four or more people. Martorano is a homicidal maniac and does other murders.  Howie not involved in them.

Howie and Sal charged with extorting folk and get prison sentence in 1978. Howie also charged with race fixing. Howie does a long bit and gets out in 1987; Sal appealed case and is murdered by a low life while waiting on appeal. That brings to an end Howie’s involvement with Whitey, Martorano, and the so-called Winter Hill gang.

(In 1979 Martorano will flee to Florida and stays away 16 years.  Joe McDonald also flees. JImmy Sims disappears but most likely murdered by McDonald.) Howie would later do time for cocaine offenses from 1993 to 2002 leaving Whitey and Flemmi as the last Mohegans who continue extorting bookies, drug dealers, and involving themselves in a murder or two. They become heads of the Winter Hill Gang consisting of themselves and people they extort from which really stretches the definition of gang.

The idea that Howie Winter knew anything about the Gardner Robbery was probably the biggest scam he pulled off. He was on the street when it happened on March 18, 1990, and knew nothing about it. He then went in the can in 1993 until 2002 for cocaine offenses. Whatever dopes hired him had no idea what they were doing but his overblown reputation made them think he had some magic.

So what does one make of this life. He’s a habitual criminal and alleged murderer who spent twenty years in prison. Is there anything one can say about such a wasted life? It is very difficult for me to find any good in a person who would take the life of another. Here, though, I find there are three things that redeem him: he joined the Marines, and if at age 14 more credit to him; he never ratted anyone out unlike every other person – Whitey, Flemmi, Martorano, Weeks, etc. – who associated with him; and his middle name was Thomas, just like mine.

May he rest in peace.

PS: It is alleged that Whitey Bulger and Stevie Flemmi ratted out Howie Winter. Not that I have anything good to say about them but that is a total fabrication. The extortion and race fixing were not because of ratting but because witnesses came forward and testified against them. The cocaine event took place after both were no longer informants. That’s the problem with so much that is written about these guys, it is totally false and one guy that seems to have the worst information is the guy who earned his street creds at Deerfield Academy.

PPS: Learn the truth about the Boston Gang Wars in my book by that name in the final stages of editing.  Soon to be released.



11 thoughts on “Howie Winter – The Leader of a Gang That Did Not Exist

  1. Hi Matt and thanks for your interesting article on your blog.

    1. Were Whitey and Stevie the enforcers during the fixing of races by the Winter Hill Gang?

    2. Wasn’t it Jimmy Sims and Mcdonald who helped to bury the bodies of Wimpy and Walter Bennett?

    3. What do you make of this article from the archives of the Boston Globe. As it seems to be an early example in the 1970’s of the informant defence that would be attempted by Flemmi in court in the 1990’s . I think that you might recognize the case and the people involved.

    1. Dave:

      Happy Thanksgiving.

      1. Howie claimed he was only a bookie. Whitey and Stevie probably did perform that role of enforcer but I’m not sure of that. The Martoranos were also involved. I’ll have to check on it.

      2. Salemme indicated he was the only one who knew the site where the Bennets were buried. Other said that they helped him but they would be Roxbury guys not Somerville guys which leaves out Sims and McDonald. That the bodies were not where Salemme said they were indicated the whole story of their burial may be a lie. Walter Bennett was said by Salemme to be murdered at late afternoon. His wife has him home around 10 p.m. and never to be seen again.

      3. Don’t remember the case. Something doesn’t ring right. I’ll want to think about it. Does, as you say, sound like the guy was using his being an informant as a defense.

  2. Howie filled out 2 draft cards, one in 1944 and the other in 1947. He claims to be 18 with a phony DOB of 12/27/26 on 12/27/44–the day he registered. Across the top a clerk wrote “Underage.” He returned in 1947 with a new tattoo an inch taller and 15 pounds heavier, two days after he actually turned 18, and the right birthdate is recorded on his registration card. It looks to me like he -tried- to join the war at 15.

    1. Joe:

      Thanks for the information. It sounds like he did try at 15 but then went in later. I guess he figured that the act of trying during the war made him a WWII veteran.

  3. wa-llahi! Winter was no gubmint cheese eating rat. Too bad about telling. Snitching is in vogue these days. When you come down in security classification, and, get to camp, you soon learn that most of the people around you are yellow rats who’d sell out anyone from their two-penny granny to the king of Siam to get out from under.

    1. Khalid:

      So right about the guys all running to squeal. One guy from Southie wrote a book saying he was the only stand up guy in Southie but in his book he pretty much squeals on the others. Maybe he saw a difference between giving info to the cops and writing about it. There was a Southie person who did not squeal. It was not a guy though. What does that tell you?

  4. “I find there are three things that redeem him…he never ratted anyone out unlike every other person….”

    Interesting. In my view, his “ratting out” fellow criminals would have redeemed him. You seem to value the code of the criminal higher than what is right and just.

    1. wa-llahi! John, what’s right, and, just, is relative. I grew up absorbing the ” three nevers”: never squeal, never steal, and, never, ever, tell on yourself.

      1. Khalid:

        Actually there were only two nevers: never steal and never squeal – telling on yourself is form of squealing.

    2. John:

      I was taught that of all the apostles Judas was the worst. What did he do? He ratted out Jesus to the Romans. I hardly find that redeems him because he cooperated with the authorities to betray his friend.

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