Howie Winter never saw Bulger coming

By Shelley Murphy
Globe Staff / July 22, 1998
  • Email|
  • Print|
  • Single Page|
  • |
Text size +

Howie Winter, who was replaced by Whitey Bulger as head of the Winter Hill gang, says "no way" did he ever suspect that Bulger was an FBI informant. And he's had 12 years in federal prison to think about it -- all of it for two cases in which Bulger has provided information to the FBI.

"It's still hard for me to believe," Winter said of recent revelations about Bulger's double-dealing, speaking from the federal penitentiary in Pennsylvania, where he's serving time for dealing drugs.

Winter's version of underworld events sharply contradicts that of former FBI agent John J. Connolly, who persuaded Bulger to turn informant in the fall of 1975.

At the time, according to Connolly, New England mob underboss Gennaro "Jerry" Angiulo was on the verge of a war with the Winter Hill gang to resolve a dispute over the placement of vending machines around Greater Boston.

Connolly said he warned Bulger that Angiulo would probably use corrupt law-enforcement contacts to set up his Winter Hill rivals, and suggested that Bulger use the FBI to turn the tables on Angiulo.

It was a deal Bulger accepted. Connolly says Bulger told him that Winter and other high-ranking members of the gang blessed the arrangement and considered him their "liaison" to the FBI.

Winter burst out laughing at Connolly's claim, insisting it was only last year, when the FBI acknowledged the ties, that he learned Bulger and his partner, Stephen "The Rifleman" Flemmi, were longtime FBI informants. Winter also said FBI reports by Connolly alleging a turf battle between the Winter Hill gang and the Mafia over vending machines were "a fantasy."

"We weren't rivals, but we were not partners either," Winter said. "Jerry Angiulo always treated me and the people around me very nice."

But Bulger and Flemmi did not. FBI reports unsealed in federal court hearings in Boston reveal that the two men told the FBI about the activities of Winter and other members of his gang.

Now federal prosecutors have urged Winter, who has four years left on a 10-year sentence, to cooperate with them against the duplicitous gangsters. He said he has refused.

"If it was my worst enemy I wouldn't cooperate against them," Winter said. "Myself, I think I'd rather take a cyanide pill than go trap someone else to save my own ass."

Winter's friendship with Flemmi dates back to the early 1960s, when they were both working for Somerville gang boss James "Buddy" McLean, who was gunned down in 1965 during the Irish gang wars.

Winter said he met Bulger in the 1970s, when Bulger enlisted his help in resolving a bloody dispute between rival gangs in South Boston. Bulger later began hanging around Winter Hill in Somerville, eventually teaming up with Flemmi.

Winter said he didn't socialize much with Bulger, but considered Flemmi a good friend.

"I thought the world of Stevie Flemmi," Winter said. "He was a man's man."

In 1979, federal prosecutors indicted 21 people -- including Winter -- in a million-dollar horse-race-fixing scheme, but removed Bulger and Flemmi from the case because they were informants. Winter spent six years in prison.

  • Email
  • Email
  • Print
  • Print
  • Single page
  • Single page
  • Reprints
  • Reprints
  • Share
  • Share
  • Comment
  • Comment
  • Share on DiggShare on Digg
  • Tag with Save this article
  • powered by
Your Name Your e-mail address (for return address purposes) E-mail address of recipients (separate multiple addresses with commas) Name and both e-mail fields are required.
Message (optional)
Disclaimer: does not share this information or keep it permanently, as it is for the sole purpose of sending this one time e-mail.