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Jimmy Flynn
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James P. Flynn (February 5, 1934 – September 12, 2022)[1] was an American teamster and film actor. He was a reputed member of the famous Winter Hill Gang.[2] He appeared in films including Good Will Hunting,[3] The Cider House Rules and What's the Worst That Could Happen?.[4]
Key Information
Biography
[edit]James P. Flynn was born in Somerville, Massachusetts.
In 1982, Flynn was wrongly identified as a shooter in the murder of Winter Hill Gang mob associate Brian "Balloonhead" Halloran and attempted murder of Michael Donahue.[5][6] He was tried and acquitted for the murder in 1986 after being framed by John Connolly and James J. Bulger.[7]
Flynn was a part of Boston's International Brotherhood of Teamsters Local 25 labor union where he later ran the organization's movie production crew. He has also been the Teamster Union's transportation coordinator and transportation captain in the transportation department on numerous films,[6][8] including The Departed, Fever Pitch and Jumanji.[9]
Flynn appeared in many films shot in the New England area. In show business he went by the name 'James P. Flynn'. Flynn was cast as a judge in the Boston-based film Good Will Hunting in 1997.[10][11] Later, he acted in the 1999 film The Cider House Rules and What's the Worst That Could Happen? in 2001.[4] He was also a truck driver for movie production equipment during the filming of My Best Friend's Girl in 2008. 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."[12]
Filmography
[edit]- Good Will Hunting (1997) as Judge George H. Malone
- The Cider House Rules (1999) as Vernon
- What's the Worst That Could Happen? (2001) as the Fire Captain
References
[edit]- ^ James P. Flynn
- ^ Carr, Howie (March 23, 2008). "Mobster of the Week: Jimmy Flynn". Boston Herald. Retrieved May 18, 2021.
- ^ Janelle Nanos (January 8, 2013). "Robin Williams on Good Will Hunting". Boston. Retrieved October 26, 2015.
- ^ a b Steve Early (March 22, 2012). "The IBT on Reality TV: Boston Union Teams Up With Mark Wahlberg". In These Times. Retrieved October 26, 2015.
- ^ Cullen, Kevin; Murphy, Shelley (February 13, 2011). Whitey Bulger: America's Most Wanted Gangster and the Manhunt That Brought Him to Justice. W. W. Norton & Company. pp. 229–230. ISBN 9780393087727. Retrieved October 26, 2015.
- ^ a b Howie Carr (June 4, 2013). Hitman: The Untold Story of Johnny Martorano---Whitey Bulger's Partner and the Most Feared Gangster in the Underworld. St. Martin's Press. pp. 198–199. ISBN 9780765365316. Retrieved October 26, 2015.
- ^ Barry, Dan (July 15, 2011). "A Voice for Those Silenced in a Mobster's Reign". The New York Times. Archived from the original on July 23, 2011. Retrieved November 22, 2021.
- ^ Jack Sullivan (August 9, 2000). "Hear no evil: Teamsters-IBT Governor Ignored Complaints of Shakedowns and Intimidation". Boston Herald. Archived from the original on April 15, 2013. Retrieved May 18, 2021 – via laborers.org.
- ^ "Jimmy Flynn". IMDB. Retrieved October 26, 2015.
- ^ Carr, Howie (2013). The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century. New York: Grand Central Publishing. ISBN 9780446506144. Retrieved May 18, 2021.
- ^ Fitzpatrick, Robert; Land, Jon (January 3, 2012). Betrayal: Whitey Bulger and the FBI Agent Who Fought to Bring Him Down. Macmillan. ISBN 9781429963664. Retrieved October 26, 2015.
- ^ The Boston Globe, "'The Departed' Has Local Launch", Carol Beggy & Mark Shanahan, 4 October 2006, Living Section, page F.2
External links
[edit]- Jimmy Flynn at IMDb
Jimmy Flynn
View on Grokipediafrom Grokipedia
Early Life
Birth and Family Background
James P. Flynn was born on February 5, 1934, in Somerville, Massachusetts.[1] Somerville, a densely populated working-class suburb adjacent to Boston, was home to a large Irish-American community during Flynn's youth, characterized by tight-knit neighborhoods and labor-oriented families.[4] Public records provide scant details on Flynn's parents or siblings, reflecting the low-profile nature of many Boston Irish families of the era who worked in trades like trucking and construction. Flynn grew up in the Winter Hill section of Somerville, where he formed childhood friendships with individuals who would later become key figures in organized crime, including James J. "Buddy" McLean, Howie Winter, Joe "The Animal" McDonald, and Jimmy Sims. These early associations, rooted in the local street culture and mutual protection networks common in mid-20th-century Irish enclaves, positioned Flynn within the emerging orbit of what would evolve into the Winter Hill Gang.[4]Early Career and Teamster Entry
James P. Flynn was born on February 5, 1934, in Somerville, Massachusetts, a neighborhood known for its tight-knit Irish-American communities and emerging organized crime networks.[10] Growing up in this environment, Flynn associated closely with figures who would later form the core of the Winter Hill Gang, including founder James "Buddy" McLean, Howie Winter, Joseph "Joe Mac" McDonald, and Jimmy Sims, connections that shaped his early social and professional circles amid Somerville's rough labor and criminal undercurrents.[4] Flynn's early career intertwined with Boston's trucking and entertainment industries, sectors dominated by the International Brotherhood of Teamsters. By the 1960s, he had aligned with Local 25, whose members frequently interacted with Winter Hill figures at venues like Marshall Motors garage in Somerville, facilitating informal networks between labor and crime.[11] He entered the union's motion picture division, handling transportation and crew operations for film productions, a role that leveraged Local 25's control over Boston-area logistics for Hollywood shoots.[4] Following his 1986 acquittal in a high-profile murder trial stemming from 1982 events, Flynn advanced to transportation coordinator for Local 25's movie crews, serving as crew chief alongside William "Billy" O’Brien for over three decades and overseeing operations marred by allegations of extortion in securing union contracts for productions.[12][4] This position solidified his influence in an industry segment where Teamster leverage often intersected with organized crime ties, though federal probes into Local 25's practices, including those involving Flynn, yielded no charges against him.[3]Criminal Associations
Involvement with Winter Hill Gang
James P. "Jimmy" Flynn, born in 1934 in Somerville, Massachusetts, maintained longstanding associations with the Winter Hill Gang, an Irish-American criminal organization that emerged in the mid-1950s and dominated organized crime in the Boston area during the 1970s and 1980s.[12] Flynn grew up in Somerville alongside foundational figures of the gang, including James "Buddy" McLean, Howie Winter, Joe "Joe Mac" McDonald, and Jimmy Sims, positioning him as an original associate from the group's early years.[4] The Winter Hill Gang, named after the Somerville neighborhood, engaged in activities such as loan sharking, gambling, hijackings, and labor racketeering, with Flynn's ties documented in federal records, including the FBI's 1975 organizational chart of the group.[4] As a prominent member of Teamsters Local 25's motion picture division, Flynn leveraged his union role to influence extortion schemes targeting film productions in the New England area by the 1980s, facilitating the gang's infiltration of legitimate industries.[4] His connections extended to key Winter Hill leaders like James "Whitey" Bulger, enabling coordination between criminal enterprises and union operations.[12] Flynn's involvement underscored the gang's reliance on local networks for protection and revenue, though his precise operational role remained peripheral compared to enforcers like Bulger or Stephen Flemmi, focusing instead on labor-based leverage.[12] These associations persisted into the late 1970s and early 1980s, amid internal feuds and external pressures from law enforcement, before escalating scrutiny led to federal raids on his properties, such as the June 2000 search of his Weymouth home, which yielded no charges.[12]1982 Murder Arrest and Legal Proceedings
On May 11, 1982, Brian Halloran, a cocaine dealer and associate of the Winter Hill Gang who had approached the FBI with information implicating James "Whitey" Bulger in other murders, was gunned down along with innocent bystander Michael Donahue, a cab driver giving Halloran a ride, on Northern Avenue in South Boston.[13] In his dying declaration, Halloran identified Jimmy Flynn, a Teamsters Local 25 member and Winter Hill associate, as one of the shooters.[12] This identification stemmed from Bulger's deliberate framing of Flynn; Bulger, the actual perpetrator alongside associates, wore a brown wig mimicking Flynn's curly hair to create the misidentification.[12] [13] Flynn was indicted on two counts of first-degree murder by August 1982, based primarily on Halloran's statement and witness accounts influenced by FBI handling of the investigation.[14] FBI agents, protecting Bulger as a confidential informant, reportedly pressured at least one eyewitness to select Flynn from a suspect list that deliberately excluded Bulger, while FBI leaks had earlier informed Bulger of Halloran's cooperation, enabling the hit.[15] [13] Flynn's trial proceeded in Suffolk County Superior Court, where defense arguments highlighted inconsistencies in witness testimonies and the absence of physical evidence linking him to the scene, including alibi corroboration from associates.[12] He was acquitted of both murder charges in 1986, with the verdict underscoring the prosecution's reliance on tainted identifications amid broader revelations of FBI corruption in protecting Bulger.[12] [15] Subsequent civil litigation, including suits by Halloran's estate against the United States, affirmed the government's role in enabling the frame-up through informant mishandling, though Flynn faced no further charges related to the incident.[13]Acting Career
Transition to Film Roles
Following his acquittal in the mid-1980s on charges related to the 1982 murders of Brian Halloran and Michael Donahue, James P. Flynn shifted focus within his longstanding career as a member of Teamsters Local 25, taking on roles as a transportation coordinator and captain for film productions in the Boston area.[12] Local 25, which supplies drivers and logistics support for motion pictures, provided Flynn access to Hollywood sets, where he handled vehicle coordination and crew transport for projects filming in Massachusetts.[5] This position, which he assumed after clearing his legal hurdles, marked his entry into the film industry, leveraging the union's monopoly on transportation services for out-of-state productions seeking tax incentives and local crews.[16] Flynn's behind-the-scenes work evolved into on-screen appearances around 1997, beginning with credited transportation duties on The Spanish Prisoner, directed by David Mamet, where his familiarity with Boston locations and crew dynamics positioned him for small roles.[2] He secured a cameo as a judge in Good Will Hunting, a Miramax film set and shot primarily in the Boston suburbs, capitalizing on his authoritative presence and local connections to portray judicial figures authentically without formal acting training.[12] This transition reflected a pattern among Local 25 members, where transportation staff occasionally "wangled" bit parts amid the influx of films to New England in the late 1990s, driven by state rebates and directors like Gus Van Sant seeking regional authenticity.[17] By the early 2000s, Flynn's dual role expanded, with acting credits in films like The Cider House Rules (1999) and Spartan (2004), often as authority figures mirroring his Teamster and reputed past associations, though he maintained no agents or auditions, relying instead on production referrals from union contacts.[8] His involvement drew federal scrutiny in 2000, as FBI raids targeted Local 25's dealings with filmmakers, including seizures from Flynn's home over alleged extortion in hiring practices, but no charges resulted, allowing his film work to continue uninterrupted.[16] This pathway underscored how organized labor's grip on film logistics facilitated opportunistic entries into acting for figures like Flynn, blending blue-collar expertise with incidental performance opportunities.[18]Notable Performances and Filmography
Flynn's acting roles were typically minor but capitalized on his genuine South Boston demeanor and local knowledge, often in films shot in the Massachusetts area. His most recognized performance was as Judge George H. Malone in Good Will Hunting (1997), where he presided over the courtroom sentencing of the protagonist, Will Hunting, played by Matt Damon; the scene underscored themes of judicial authority and redemption in the Gus Van Sant-directed drama, which earned nine Academy Award nominations including Best Picture.[19][12] In The Cider House Rules (1999), Flynn portrayed Vernon, a cider house worker in the Lasse Hallström adaptation of John Irving's novel, contributing to the film's depiction of rural New England life amid its exploration of orphanage ethics and personal autonomy; the movie won two Oscars, for Best Director and Best Adapted Screenplay.[2] Flynn also appeared as a security guard in What's the Worst That Could Happen? (2001), a comedy directed by Sam Weisman starring Martin Lawrence and Danny DeVito, where his brief role highlighted confrontational exchanges in a heist narrative. Additional small parts included uncredited or minor appearances in The Spanish Prisoner (1997), a David Mamet con-artist thriller, and Spartan (2004), a political thriller by David Mamet featuring Val Kilmer.[2][20]Filmography (Acting Roles)
| Year | Title | Role | Notes |
|---|---|---|---|
| 1997 | Good Will Hunting | Judge George H. Malone | Courtroom judge in key trial scene[19] |
| 1997 | The Spanish Prisoner | (Minor/unspecified) | Supporting appearance[2] |
| 1999 | The Cider House Rules | Vernon | Cider house laborer |
| 2001 | What's the Worst That Could Happen? | Security Guard | Brief confrontational role |
| 2004 | Spartan | (Minor/unspecified) | Supporting appearance[20] |