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Jimmy Flynn

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Jimmy Flynn
BornJames P. Flynn
Occupation(s)Actor and Teamster

James P. "Jimmy" Flynn (born February 5, 1934) is an American teamster and film actor. He was a reputed member of the famous Winter Hill Gang.

James P. Flynn was born in Somerville, Massachusetts and lived at 115 Hibiscus Avenue in Weymouth, Massachusetts. He stood at 6 ft tall and weighed 180 pounds with blue eyes and blonde hair. He was arrested in Billerica, Massachusetts in the washroom of a Chinese restaurant. He was framed with the help of John Connolly and James J. Bulger for the murder of Winter Hill Gang mob associate Brian (Ballonhead) Halloran and attempted murder of Michael Donahue, who offered to drive the intoxicated Halloran home in South Boston, Massachusetts.


In 1986 he was tried and acquitted for that murder. He was used as an F.B.I. informant by agent John Connolly in the 1980s.

Flynn appeared in many films shot in the New England area. He has also been the Teamster Union's coordinator on film shoots. One of his best friends is Stephen "The Rifleman" Flemmi, a professional hitman who has since been released from prison. Flynn can be seen in such films as Good Will Hunting, The Cider House Rules and What's the Worst That Could Happen?

Boston actor Tom Kemp remarked that the film The Departed, "wouldn't be a Boston movie without me, a Wahlberg, and Jimmy Flynn from the teamsters."


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