Good Times for Old Men: Howie Winter Walks!

howie-winter1I called the Middlesex DA’s office the other day to check up on Howie Winter’s case. You remember Howie, he was the guy John Martorano was with him when they were killing some of the people on behalf of Gerry Angiulo the Boston Mafia leader. Martorano testified how he and Howie met with Angiulo who was worried about another group led by Indian Al which was moving in on his gaming empire. Gerry hired Martorano and Howie and their merry men to wipe out Indian Al and his gang. In Boston at those times whatever Gerry wanted, Gerry got.

So they set about to do the job and did it very well. From John Martorano, the man who said you can’t rat on a rat, we learned that he did rat on Howie Winter who had never ratted on anyone. Nor had Howie ever been put in any FBI file as an informant. He told the feds to take a walk.

Howie’s attitude was that he was a criminal, he hung out with other criminals, and if he got jammed in that was his problem. He and Catherine Greig are the only people who it is clear have not ratted out anyone in the Whitey saga.

Some say Catherine is doing hard time. Here’s their argument. She’s not a criminal. Her only crime in her fifty odd years was being with Whitey on his flight. For that she got eight years. She’s learned prison isn’t fun. She’s still got a long way to go. They say she’ll cooperate. I’m doubtful. But I’ve been wrong before so we’ll just have to see. Does she know where Whitey’s money is hidden? Will that be enough for her to get a reduction? Or will she have to come up with something about people who may have been helping them out on the run that fits into the statute of limitations?

If Catherine folds then that would only leave Howie who never ratted anyone out or wrote a book. Watch, the next thing I’ll hear is that Howie is writing a book. Won’t that be a disappointment?

howie-winterHowie was put out of business back in the late 1970s. It wasn’t the famous Race Fix Case that did him in, it was a case of extortion that he and his buddy Sal Sperlinger got caught up in that garnered Howie an 18 year sentence. Although he was part of the Race Fix Case that had little to do with his first time in prison from ’79 to ’87. In ’93 he did another ten for some cocaine offense. He got out in 2002.

In June 2012 at 83-years-old he was again charged. This time with attempted extortion. Along with him was his young friend James Melville, age 70.

(1) SpuckyHowie came to mind because of the arrest of the two Mafia guys in Boston the other day. The acting boss of the New England Mafia, Anthony “Spucky” Spagnolo, 72, aka, Crazy Eyes, and another associate, Pryce “Stretch” Quintina, 74.  They appeared in U.S. District Court in Boston following their morning arrests. After their arraignment they were both let out on bail.

I couldn’t figure how Mafia guys with prior incarcerations for violent crimes, one who is the acting boss, can walk out of the courthouse. I went back and read how Judge Mark Wolf let Spucky out back in 1990. It seems from reading his decision he had a warm spot in his heart for the Mafia.

I figured this time the guys were let out because of their age. That got me thinking of Howie. It was over two years since his arrest. I wondered about the status of his case.

You know he was the head of the Winter Hill Gang. I talked to someone who once saw him with all of his deadly crew. It was clear he called the shots according to what was explained to me. Remember earlier this week  I told how Judge Selya said: “The federal courts are by now painfully familiar with the Winter Hill Gang.”

Howie as its leader is implicated in murders by Martorano, imprisoned for at least two long stretches and now facing another charge relating to extortion. I’m sort of figuring they’re going to throw the book at him.

The Middlesex DA’s office as promised called me back. I was advised by message that Howie had pled guilty way back on April 2, 2014. His sentence was 5 years probation. I guess the book missed him.

I can’t really say whether the sentence was right or wrong. I don’t know what evidence the DA had. I can’t say I’m disappointed. It seems only fair that the one guy who didn’t become a rat should get a break.

I’d guess Howie is 85 now, the two Mafia guys are in their 70s. They’re still throwing their weight around. The courts seem not to mind. These are good times for old timers. It all reminds me of what General Douglas MacArthur said about old soldiers. I have to change it just a bit when it comes to old criminals. “Old criminals never die, they keep plugging along.”



10 thoughts on “Good Times for Old Men: Howie Winter Walks!

  1. Matt,
    Don’t you think Red Shea deserves an honorable mention up there with Howie and Cathy?

  2. The boys gathered around the Green Mountain Coffee dispenser at Flying Pond Variety this morning said “. tell Matt they
    could smell the FBI sulphur all the way
    up here in Maine, ayuh!”

    In other news tell Matt I got tickets for us next weekend for the Patriots game where Metallica will perform the music from Arnold Schoenberg’s ‘ late period’ during

    my friend Ed Tatro has been researching the JFK assassination
    for 50 years

    He spoke last weekend at this conference.

    watch him in the banned documentary
    the guilty men
    google the title with the word jfk

    1. Jim:

      A good source tells how he was at an affair. Howie came in with others including Whitey. They were about to sit down and Whitey was about to take the chair next to him and Howie told him to mover somewhere else and he motioned for another one of their guys to sit next to him. There’s also that Whitey went to Howie for his help in stopping the Mullins from coming after him. Howie was the leader of the Winter gang that included himself, Jimmy Sims and Joe McDonald, all three very tough killers. Whitey had no reputation when he joined in 1972. Whitey would only become prominent after Howie went to the can in 1978 when he and Flemmi had no opposition within the group. The Winter gang had disbanded and Martorano had fled.

  3. they reference US V. Winter a few times in Whitey’s Appeal as well, he has to have a Nee-like deal. Matarano (or his incredible Lawyer) worked out a deal for him to have his friends never charged for any crimes past or future if he was going to become a government witness as all familiar with this case know.

    1. Jim:

      Martorano had a lawyer who was recognized at the best in Boston. I happened to have worked for him for several years so I knew his ability and he did take the store from Wyshak who probably feared him. It is amazing that Winter, Nee, Martorano’s brother, and some others were given passes just to get Whitey.

  4. Nc: I don’t think there is any dispute that one time Howie was the head of Winter Hill. But I doubt he ordered the hit on Halloran, because at the time of the hit he was about 3 years into his 18 year sentence. Not sure what he would have to gain by implicating himself in another murder while he was locked up. Halloran had somebody jammed in, whether that be Whitey, Flemmi, Martorano or some combination thereof, or all three.

    1. Dave:

      Winter didn’t order the hit on Halloran. Had he not been in the can he might have prevented it for I hear he had a close relationship with him. Halloran was not giving any information to the FBI against Winter. Whitey hit Halloran because he heard he had implicated him in the Wheeler murder.

  5. Winter ordered the murder of Spike O’Toole, Connors and Halloran among others. He was never charged because he has a relationship with the Feds. He along with Nee, Martorano et al have relationships with the Feds that is why they are free. The Feds concocted the myth of Whitey as the greatest criminal. If they charged Winter his trial would expose that he was the Head of the Winter Hill gang. He gave the orders. He had the connection to the Mafia. This would undercut the invented version that the Feds and the press created. The press and the Feds are essentially Mafia Deniers. They downplay their role as much as possible. Was it Wyshak or Wolfe who called them the JV? The Historian Hastings said at wartime the press produces only hyperbole, fantasy and deceit. They apply the same principles in covering crime.

    1. NC:

      Agree with Dave that Winter didn’t order the hit or Halloran. Have to check on O’Toole because he was involved in the dispute with Flemmi having shot Jimmy the Bear. Connors was probably part of Winter’s doings.

      I don’t believe Howie has a relationship with Feds other than the deal Martorano made that he would not have to testify against him; Weeks made the same deal for Nee.

      Howie was connected to the Mafia and was the head of Winter Hill up until he went to prison for ten or so years in 1978. It was after he went that Whitey and Stevie took over the gang since all the original members were no longer around.

      It was Obama that called ISIS the JVs.

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