James P. Flynn (born February 5, 1934 in Boston, Massachusetts) was an Irish-American Bostonian, teamster, and film actor. He was a reputed member of the famous Winter Hill Gang.
Jimmy Flynn has 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 "The Rifleman" Stephen Flemmi, a professional hitman spending time in prison.
In 2000 Flynn ordered a snack truck owner and operator Susan Christy who was working on the film set of "What's the Worst That Could Happen," to quit in order for his friend and fellow Teamster Robert Martini to get the business with his truck. When Christy refused Flynn threatened her equipment. Flynn told Martini that Christy would have to be killed or else people would "lose respect" for him. He told Martini that he should be the one to murder her since he would be the one to ultimately benefit from the deed. When George Cashman heard the plan he called Flynn to task and ordered him not to kill her but to send her a message. On August 15, 2000 while the movie was being shot Christy was attacked by Teamster Bartley Small. Christy reported the incident to the police but ultimately never filed charges.
Flynn is still currently under indictment by the United States federal government for racketeering.
As an actor Flynn can be seen in such films as Good Will Hunting, The Cider House Rules and What's the Worst that Could Happen?
Under the pretext of producing a movie, the FBI planned to catch people taking bribes in exchange for not making trouble when filmmakers used non-union truck drivers and non-union crew members on movie shoots in Boston. Film shooting actually occurred in several cities including New Orleans and Las Vegas, while in other major cities, evidence was obtained without using an actual crew made up of FBI personnel. As the investigation progressed from city to city, sealed indictments were obtained and only unsealed when the operation was concluded. A film on this FBI sting was made called "The Last Shot", starring Alec Baldwin.
Boston actor Tom Kemp remarked: "(The film The Departed) wouldn't be a Boston movie without me, a Wahlberg, and Jimmy Flynn from the teamsters."