The Real-Life Gangsters Behind The Departed, Explained



  • Scorsese’s
    The Departed
    is a crime masterpiece inspired by real gangsters like Whitey Bulger.
  • Jack Nicholson’s chaotic portrayal of gangster Frank Costello adds unforgettable intensity to the film.
  • Matt Damon’s character, Colin Sullivan, is based on FBI agent John Connolly, adding depth to the story.

Martin Scorsese’s 2006 American crime thriller The Departed marked the fourth time the critically acclaimed director had a feature reach number one at the box office. Often considered among his best works, the film not only topped the list of best films of 2006 on many lists, including Richard Roeper’s list for Ebert and Roeper, but it would also clean up during the award season, winning four Oscars at the 2007 Academy Awards, including Best Director and Best Adapted Screenplay.

The movie still resonates as one of Scorsese’s best works and continues to stand out in the crime genre. As with many movies that perfectly tap into the world of crime, the movie drew inspiration from real people and events. We will look at the real-life gangsters who inspired Martin Scorsese’s The Departed and other inspirations behind the film.

The Making of The Departed

Directed by Martin Scorsese and written by William Monahan, The Departed follows Irish Mob boss Frank Costello (Jack Nicholson) planting a spy, Colin Sullivan (Matt Damon), within the Massachusetts State Police. At the same time, the police assign an undercover state trooper, Billy Costigan (Leonardo DiCaprio), to infiltrate Costello’s mob crew. When both sides catch on to having someone infiltrating them, it sparks a race between them to expose the other while they struggle with their loyalty built up through years of playing undercover roles.


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The movie was a remake, of sorts, looking to re-envision the acclaimed Hong Kong crime-thrillerInfernal Affairs (2002). While considered a remake, there are plenty of key differences between the two in both story and visual approaches, and they both have their strengths and weaknesses when compared; for example, Infernal Affairs is often attributed to having better character development, while The Departed is generally considered more visually engaging. Still, this remains more based on opinion. But where the films do differ largely is in their inspiration. Notably, The Departed drew its inspiration for Frank Costello from the notorious Joseph “Whitey” Bulger Jr. and his criminal activities as leader of the Winter Hill Gang.

Who Was Joseph “Whitey” Bulger Jr.?

Born on September 3, 1929, in Boston, Massachusetts, Bulger was the boss of the Winter Hill Gang in the Winter Hill neighborhood of Somerville, Massachusetts, holding the position from the 1970s into the 1990s. The length of his reign and his longevity largely contributed to his work as a high-level FBI Informant, making him a reviled figure as his connections led to the deaths of many other prominent mob members and associates.

Still, from the beginning, Bulger was a prominent figure due to his penchant for violence, which started at a young age when he earned his first arrest at the age of 14 and was sent to an infirmary. From there, his criminal record would only continue to grow, including military charges during his stint in the Air Force from 1948-52. In 1956, he was convicted of federal charges of hijacking and served time in infamous federal prisons such as Atlanta, Alcatraz, Leavenworth, and Lewisburg.


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What can be seen as complicating the already violent persona of Bulger Jr. was his choice of opting into the CIA program that dosed prisoners with the hallucinatory drug LSD in return for lesser sentences. His involvement in the program is more a side-note, but given the appalling history of the CIA drug experiments and the effects it had on multiple ‘participants,’ it is noteworthy in both seeing Bulger form connections with government agencies for his work with the FBI from 1975 to 1990, but also gives insight into the psyche of the infamous mob boss who was likely mentally-damaged by government negligence.

Regardless, Joseph “Whitey” Bulger Jr. was a fascinating figure whose actions made him the target of mob justice, leading to his eventual violent murder in prison in 2018. The Winter Hill Gang, which has been described as a loose confederation with no official leader of the gang but rather influential leaders of different crews within the organization, was at its most prominent under Whitey Bulger’s rule. The gang is rumored to still be active, yet diminished, with others stating it is no longer active at all.

He proved to be a fascinating figure to focus The Departed on. Jack Nicholson reveled in playing such a chaotic role, with the actor going as far as to rewrite his own character and add additional scenes. The shoot was generally considered pretty chaotic, with Nicholson embracing the role, which created discomfort on set but ultimately led to one of the most unforgettable performances by the seasoned actor.

While Nicholson’s Portrayal of Frank Costello drew inspiration from real-life gangster Joseph “Whitey” Bulger Jr., his character was not the only one inspired by real people. Matt Damon’s character, Colin Sullivan, was based on FBI agent John Connolly. Connolly would also become a contentious figure for his work with the FBI, and his actions with Bulger eventually led to him being convicted of second-degree murder in 2008; you can read more about his involvement with the FBI and Whitey Bulger on the ATI site.


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Where to Watch The Departed

the departed

The Departed

Release Date
October 5, 2006

Martin Scorsese

The Departed is available to stream on Apple TV+ or for rent/purchase through Prime or Apple TV+. If you want to check out the film on which The Departed was loosely based and get a better understanding of the process going into adapting the Hong Kong thriller, you can stream Infernal Affairs on Apple TV+ or The Criterion Channel.



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