Flemmi details his, Bulger’s relationship with FBI

whitey bulger boston kevin weeks flemmi
Stephen Flemmi, Whitey Bulger and Kevin Weeks on another walk around Castle Island.
Credit: US Attorney’s office

Winter Hill Gang leader Stephen Flemmi detailed on Friday how members of the Winter Hill Gang were able to avoid indictments for years – a growing relationship with FBI agents that led to tip-offs. 

Flemmi, 79, took the witness stand for a second day to testify against his former crime partner James “Whitey” Bulger.

Flemmi, under direct questioning by Assistant US Attorney Fred Wyshak, recounted how the Winter Hill Gang’s relationship with the FBI grew.

He talked about the time when Bulger approached the leaders of the gang and asked for permission to talk to FBI agent John Connolly. Flemmi said they agreed because it was always good to have law enforcement sources.

“As open as we were and the notoriety we had, it’d be very difficult to survive” without law enforcement sources, Flemmi said.

Bulger came back to the gang leadership after meeting Connolly and filled them in on what Connolly said.

“He said that John Connolly approached him and said during meeting the mafia had their sources and that ‘we could help you.’ [Connolly] said ‘if [the mafia] wanted to play checkers, we can play chess,’” Flemmi said.

Flemmi said he came to know former FBI agent Paul Rico through his involvement in another gang in the late 1950s. Rico was the one who called Flemmi early one morning in the 1960s before an indictment was about to come down. The tip led Flemmi to flee to California, New York, Florida and eventually Montreal for years.

Flemmi’s testimony was expected to last through the day and possibly into Monday.

Follow Michael Naughton on Twitter @metrobosmike.


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