WHITEY & THE FBI
Howie Winter never saw Bulger coming
By Shelley Murphy, Globe Staff, 7/22/1998
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
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
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
Winter said he didn't socialize much with Bulger, but considered Flemmi a
``I thought the world of Stevie Flemmi,'' Winter said. ``He was a man's
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.
This story ran on page A22 of the Boston Globe on 07/22/1998.
© Copyright 1998 Globe Newspaper Company.