Characters / The Departed

The Rats

Billy Costigan

William M. "Billy" Costigan Jr.

Played By: Leonardo DiCaprio

"You sit there with a mass murderer. A mass murderer. Your heart rate is jacked, and your hand... steady. That's one thing I figured out about myself in prison. My hand does not shake... ever."

A Massachusetts State Trooper who is selected to become a mole in Frank Costello's organisation.

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• Anti-Hero: He has to do some really shady things while undercover, such as participating in murder. Granted, his therapy sessions and behind-the-scenes turmoil show that he absolutely doesn't enjoy doing it.
• Big, Screwed-Up Family: His paternal family are mostly shady crooks (and are mostly dead or in prison), save for his father, a baggage handler who married an Uptown Girl, but later divorced her, with Billy going back and forth between their households. His mother's family is implied to have looked down on his father, and only one maternal cousin bothered to attended William Sr.'s funeral, or remain in close enough contact with Billy afterwards to find out he planned to become a cop. He flat out says to his mom's brother that he doesn't want anything to do with him after her funeral, but also seems a little ashamed of his paternal relatives, especially when Queenan and Dignam grill him over them.
• Boom, Headshot!: How he was killed by Barrigan.
• Broken Ace: He's a certified genius, a skilled fighter, and a competent policeman and criminal. But, he also suffers a tremendous amount of stress from what he is forced to do in the mob, and has a lot of clear psychological issues.
• Cultured Badass: He actually went to decent schools and got excellent grades as noted by Dignam and Queenan, he could actually have had a better career but he really wants to be a cop. He also quotes Nathaniel Hawthorne.
• Deadpan Snarker: Another defense mechanism to deal with the stress of being undercover.
• Didn't See That Coming: There's no way he could have anticipated being taken down like that. He called for backup by calling Brown, he mailed the evidence (making copies) and sent it to the police shrink but it takes a Diabolus ex Nihilo, a second mole, to take him out with no warning.
• Dropped a Bridge on Him: Right as Costigan is about to arrest Sullivan and be the hero, he is shot in the head completely out of nowhere.
• Expy: His undercover legend of being a former State trooper is analogous to the real-life story of Richard Marinick, a former State trooper who joined Whitey Bulger's gang.
• Foil: To Sullivan.
• Good Is Not Nice: He's quite abrasive, contrasting to the usually calm Sullivan.
• Hair-Trigger Temper: He's like this as the result of the stress of being a mole though he's had a record with it prior, even getting kicked out of school for attacking a teacher.
• The Hero: As the film's protagonist.
• Hero with Bad Publicity: As an undercover cop who must resort to shady things to gain Costello's trust he's this in the eyes of the police department aside from Queenan and Dignam. Enforced when Sullivan deletes all records of him being an undercover cop, then defied when Sullivan, in order to maintain his own cover, reveals that Costigan was an undercover trooper in order to pin everything on Barrigan. Costigan winds up being posthumously given the Medal of Merit and a departmental funeral.
• Heroic BSoD: He's utterly devastated when Queenan dies in front of him.
• Jerkass Has a Point: When he gives a "The Reason You Suck" Speech to his Uncle Edward, the one point that sticks with the man is Billy calling him out for doing nothing to help out Billy's mother as she was dying from cancer.
• Jerk with a Heart of Gold: His jerk behavior is due to the stress of being undercover within the organization of a murderous madman like Costello.
• The Mole: He's a mole for the Massachusetts State Police inside Costello's organization.
• Mysterious Middle Initial: His police file reveals that his middle name begins with M, but we never find out what it stands for.
• No-Holds-Barred Beatdown: Costigan is quite skilled at dishing these out at a moment's notice. It's one of the things that gets him noticed by Costello and his gang.
• Obfuscating Stupidity: Exceptionally intelligent, as noted by Dignam, but pretends to be Book Dumb around Costello in hopes of leading Costello to believe that he's too stupid to be a mole.
  Costello: You know John Lennon?
  Costigan: Yeah, he was President before Lincoln.
• Politically Incorrect Hero: Refers to Sullivan as a "two-faced faggot."
• Real Men Wear Pink: His drink of choice is cranberry juice. The one guy who questions his masculinity on this gets a face full of glass.
• Red Oni, Blue Oni: He's the Red to Sullivan's Blue.
• Sanity Slippage: Due to the stresses of being undercover and then by Queenan's death.
• Sir Swears-a-Lot: He utters the "F" word almost continually especially when he's really angry.
• Sixth Ranger Traitor: To Costello.
• Someone to Remember Him By: It's strongly implied that he is the father of Madolyn's unborn child.
• Surprisingly Sudden Death: He's killed by a shot to the head instantly by Barrigan and with no warning whatsoever.
• Unperson: When Sullivan erases all records of him being an undercover.
• Throw the Dog a Bone: A postmortem example. Despite Costigan's death, Sullivan clearing his record and pinning everything on Barrigan results in Costigan posthumously receiving the Medal of Merit and a full police funeral. After all the stress and trauma that ended with his death, he at least got to at least somewhat redeem his family in the eyes of the police and public.
• Troubled, but Cute: According to Madolyn.

Colin Sullivan

Staff Sergeant Colin Sullivan

Played By: Matt Damon

A member of Frank Costello's criminal organization sent to infiltrate the Massachusetts State Police.

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• The Ace: What he appears to be. Handsome, charming, intelligent, respected and a hard worker. No one suspects he's really Costello's mole.
• Adaptational Villainy: Like his Infernal Affairs counterpart Lau Kin-ming, both of them betrayed and killed their own bosses. However, unlike Lau, who betrayed Hon Sam out of his guilt over causing the death of Superintendent Wong, Sullivan does this to Costello out of fear of Costello ratting him out to the FBI.
• All for Nothing: Sullivan's very upset to discover that Costello has been an FBI informant the entire time and always planned to sell him out. Any remaining plans he might have had to continue his ambitions to go to Harvard and become legitimate after the deaths of Costigan and Barrigan are rendered moot when Dignam kills him anyway. Costigan had also given evidence of Sullivan being the mole to Madolyn, and Costello almost certainly included Sullivan in the evidence he sent to the FBI before his death. Basically, no matter what happened, Sullivan was ultimately never going to escape retribution.
• Asshole Victim: At the end of the film, thanks to Dignam.
• Bitch in Sheep's Clothing: Even though he's Costello's mole, he keeps a squeaky clean record to ascend and avoid suspicion.
• Boom, Headshot!: Given to him by Dignam. He gives one to Barrigan who whacked Costigan the same way.
• Chronic Backstabbing Disorder: Kills Costello and Barrigan to avoid being ever found out as a mole.
• Detective Mole: He's charged with finding the mole in the Massachusetts State Police - himself.
• Dirty Cop: He's Costello's mole inside the Massachusetts State Police.
• Dirty Coward: He'll do anything not be exposed and risk going to jail. Even, killing his own best friend and outing him as the sole rat to save himself from suspicion.
• Disappeared Dad: Costello takes over.
• Dragon Ascendant: After Costello dies, Billy discovers that Sullivan is the mole inside the police that was working for the gangster and puts all his efforts to detain him.
• Elite School Means Elite Brain: Billy is a genius who wants to go to Harvard and is both extremely intelligent, cultured, and pragmatic.
• Evil Genius: For Costello.
• Expy: Of FBI Special Agent John Connolly, Whitey Bulger's inside man within law enforcement.
• Face Death with Dignity: Doesn't try to beg or run away and simply accepts his fate with a dejected "Okay" when Dignam has him at gunpoint.
• Foil: To Costigan. These Massachusetts State Police troopers are sent to find the mole in their respective organizations. Whereas Costigan is a clean cop with a criminal record, Sullivan is a dirty cop with a squeaky clean record.
• The Friend Nobody Likes: Many of his fellow troopers and especially Dignam can hardly stand him and think that he’s just a kiss ass trying to get ahead in the ranks. The only one who does like him as Ellerby.
• Hired to Hunt Yourself: Tasked with finding Costello's mole: Himself.
• Humiliation Conga: He discovers that all of his years working for Costello were for nothing upon learning that Costello was an FBI informant the entire time, had no loyalty to him, and likely planned on ratting him out eventually anyway. He loses his girlfriend when she discovers that he's a mole and ends up alone and miserable despite managing to parlay his criminal past into a legitimate career. Then Dignam kills him at his apartment anyway.
• It's All About Me: Colin is his own first and highest priority.
• Jerkass: What he is at heart. Though he's genuinely a decent boyfriend to Madolyn, until she finds out that he's a mole, she doesn't consider not breaking up with him, even hoping to start a family with him with a child that may or may not be his.
• Karma Houdini Warranty: Sullivan thinks he got away from being discovered when Billy dies and frames the treason to Barrigan. Then Dignam waits for him in his apartment and kills him.
• The Loins Sleep Tonight: Implied to be impotent. After spending a night with Madolyn, the next morning she comments that it is a lot more common of a problem than guys think. When Ellerby says that getting married is a sign to women of an active libido, Colin awkwardly exaggerates his sexual activities to hide his insecurity. Due to his impotency, it is implied that Madolyn is pregnant with Billy's child.
• Mole in Charge: When he takes over Queenan's unit.
• Pet the Dog: There are hints that he feels guilty about what happened to Costigan such as pushing for him to receive a posthumous medal of merit and his resigned acceptance when Dignam comes to kill him.
• Politically Incorrect Villain: Derisively refers to the fire fighters as a bunch of "queers" and "homos."
• Professional Butt-Kisser: How the rest of the cops see him.
• Raised by Grandparents: He was living with his grandmother the first time Costello met him and offered him a job, for unknown reasons.
• Red Oni, Blue Oni: Sullivan is the Blue to Costigan's Red.
• Screw the Rules, I Make Them!: Even if he's a mole, his important, elite status in the police force goes to his head when he screams at Dignam after Queenan's death that as he's Internal Investigation Services, he can investigate whoever he wants.
• The Starscream: He ends up betraying and killing Costello after finding out Costello's an FBI informant and was ready to expose him to the Feds.
• Too Annoyed to Be Afraid: Normally reacts to the escalating danger of his predicament with the appropriate level of fear, undergoing a full-blown Villainous Breakdown complete with tears when it looks like he's going to be unmasked as Costello's mole in the police department. However, when he finds himself cornered in his apartment by a gun-toting assassin AKA Sergeant Dignam, Colin is so burnt out by everything that's happened over the course of the finale that he responds with an exasperated-sounding "okay," as if annoyed that his day somehow got worse. Immediately afterwards, Dignam shoots Colin in the head, killing him instantly.
• Ungrateful Bastard: To Costello.
• Villain Protagonist: He has a great amount of screen time and character development as Billy, yet he is one of the main villains of the film.
• Villain with Good Publicity: He creates an image for himself as an intelligent, hard-working and generally likable person to cover that he's really a mole. Only Dignam sees through it.
• Villainous Breakdown: After failing to convince Billy to kill him, he can only sob. He recovers, more or less, after Barrigan kills the honest officers.
  Colin: Just fucking kill me.
• Wicked Cultured: As a young boy he gets a James Joyce reference and later discusses Freud seriously with a shrink. More to the point he wants to study law and apply himself and make it into Harvard, and maybe become legitimate.

The Police

Oliver Queenan

Captain Oliver Charles Queenan

Played By: Martin Sheen

Costigan's handler in the Massachusetts State Police.

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• Benevolent Boss: He's a caring and good-natured man.
• Big Good: Along with Ellerby.
• Captain Smooth and Sergeant Rough: Captain Smooth to Dignam's Sergeant Rough.
• Cool Old Guy: He's the nicest character in the movie. Even Dignam is noticeably more respectful of him than anyone else he works with.
• Defiant to the End: He dies without ever ratting Costigan out.
• Destination Defenestration: The rooftop version, when Costello's men execute him by throwing him off of one. Billy arrives just in time to see him hit the ground bloodily right in front of him.
• Face Death with Dignity: He performs a Heroic Sacrifice to save Costigan and the whole operation when Costello's men were arriving to the building.
• A Father to His Men: He really cares about the men he oversees. When Billy goes to Queenan's home, he offers him some food and beverages to the young man.
• The Good Captain: Best exemplified in a scene where he is visited by Costigan in the middle of the night to give some important info. Queenan takes him in, even gives him some food and brings him water which shows he genuinely cares for him.
• Heroic Sacrifice: He lets some of Costello's boys pitch him to his death to keep Costigan's cover secure.
• Reasonable Authority Figure: He is a calm fatherly man who gives some sense when tension arises and he was willing to sacrifice his own life to hide Billy's identity and the whole operation to stop Costello.
• Team Dad: To the undercovers.

George Ellerby

Captain George Ellerby

Played By: Alec Baldwin

Colin Sullivan's superior and the one in charge for any active operation against Costello.

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• Benevolent Boss: He's a pretty friendly guy, especially compared to Dignam.
• Beware the Nice Ones: He seems to be as reasonable as Queenan, but he can get easily excited and does not accept stupid failures easily. When the FBI didn't placed the cameras correctly in the meeting between Costello and the Chinese dealers, he almost beat the technician in charge.
• Big Good: Along with Queenan.
• The Captain: The second police captain in charge in the operation against mobster Frank Costello. He leads the action operations.
• Da Chief: His role in the film.
• Deadpan Snarker: He's fond of mixing slightly grim jokes into his briefings.
• Functional Addict: Seems to have a drinking problem. He's intelligent and pretty good at his job, but we see him apparently nursing a hangover at HQ. This is more evident in the screenplay.
• Horrible Judge of Character: He trusts Sullivan completely while treating Dignam with disdain. He even says to Sullivan that the latter's clean record would make any other cop suspicious but doesn't phase him.

"You have an immaculate record. Some people don't trust a guy with an immaculate record. I do." [Hits golfball]. "I had an immaculate record."

• Jerk with a Heart of Gold: He's pretty abrasive and insensitive (although a far cry from Dignam), but well-meaning and a good boss.
• Large Ham: When he gets angry or flustered, he's this.
• Unwitting Instigator of Doom: Playing favorites with Sullivan causes several problems for the police throughout the film. He's the one who puts Sullivan in charge of finding Costello's mole in the police and his suspension of Dignam later in the film prevents Dignam from arriving with Brown to help Costigan arrest Sullivan, leading to several deaths.
• Vitriolic Best Buds: With Dignam. The two have worked together long enough that Ellerby takes his foul-mouthed abuse in stride and even matches him in turn.
• You Remind Me of X: Ellerby does not suspect that Colin Sullivan is Costello's mole because he sees him as a younger version of himself.

Sean Dignam

Staff Sergeant Sean Dignam

Played By: Mark Wahlberg

A tough sergeant and the Number Two for Captain Queenan.

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• Canon Foreigner: While the movie is far from a one-to-one remake of Infernal Affairs, Dignam is notable for being the only major character with no equivalent to the original movie series. He exists purely to ensure that Sullivan, whose IA equivalent got away with all of his crimes, doesn't get to survive the movie this time.
• Captain Smooth and Sergeant Rough: Sergeant Rough to Queenan's Captain Smooth.
• Chekhov's Gunman: Appears at the end to kill Sullivan.
• Cluster F-Bomb: Stands out in a film full of them.
• Cowboy Cop: Doesn't mind enacting justice on his own terms, outside police procedure.
• Deadpan Snarker: His snarky lines provide most of the tension breakers in the film.
  "I'm the guy who does his job. You must be the other guy."
• Deus ex Machina: When it looks like Sullivan is about to get away with his crimes, he appears in the end to kill Sullivan in revenge. It's implied that he was shown the incriminating tapes by Madolyn, confirming his suspicions.
• Excellent Judge of Character: He reads Costigan like an open book in their first interview, is the only one to see through Sullivan's charismatic charmer persona, and correctly identifies Captain Ellerby as well-meaning but unable to spot the corruption under his nose.
• Expy: Mark stated he was emulating every cop that had arrested him as a child as well as his own parents when they had to pay his bail with the grocery money.
• The Friend Nobody Likes: Other than Captain Queenan, pretty much none of his colleagues like him due to his abrasive personality. Even Queenan admits that Dignam's personality is something they'll had to learn to get used to.
• The Gadfly: Is completely committed to pissing off and pushing the buttons of everyone except Queenan. One example is whenever he walks past the office where the feds (who are also after Costello) work, he makes it a point to give them the finger.
• Good Is Not Nice: He is a rude, obnoxious bully who needlessly antagonizes everyone he comes in contact with, but is dedicated to the job and fiercely loyal to Queenan. He saw to it that Queenan's death, as well as Costigan's, were avenged.
• Hair-Trigger Temper: He's very quick to resort to physical attacks.
• Hates Everyone Equally: He doesn't particularly hate most of the people he antagonizes and bullies; he's just an abrasive, foul-mouthed person by nature. There are even hints that he actually likes Billy a little, sincerely telling him that he's too smart to be a trooper, and his antagonism of Ellerby has a certain mutual affection. It's only Sullivan who genuinely draws Dignam's ire which turns out to be for good reasons.
• Jerkass Has a Point:
  • He loathes Sullivan in particular, which is of course entirely justified. Pretty much everything he says about Sullivan being willing do anything for a promotion is very prescient.
  • He reminds Costigan that being an undercover cop doesn't give him the freedom to commit any felony, even if its to maintain his cover. Specifically, the guy whose jaw he breaks in one scene is actually an undercover BPD officer and Billy's actions have created headaches for Queenan and Dignam as a result.
  • As harsh and borderline sadistic as it is, his assessment of Billy, that he's caught between two worlds and trying to become a trooper simply to distance himself from his family's criminal background, is also devastatingly accurate.
• Jerk with a Heart of Gold: Few of his co-workers could stand being around him, but for all his rudeness he's quite fond of Queenan and wants to stop Costello's criminal empire and does have a few scattered moments of kindness throughout, even to Billy.
  • There's a scene where he goads Billy until Billy punches him, and one Youtube comment theorized that he did it deliberately, to let Billy blow off steam. He's even smiling afterward.
• The Lancer: To Queenan
• Number Two: For Queenan.
• Officer O'Hara: He's a swearer, and he's also played by native Bostonian Mark Wahlberg, who uses his native accent instead of anything else. Ironically, he goads Billy by calling him "lace-curtain (well-off or trying to look like they're well off) Irish".
• O.O.C. Is Serious Business: He is utterly silent when assassinating Sullivan, a far cry from how he usually is.
• Pet the Dog:
  • He tells Billy that, with his intellect, he can do a lot more than being a state trooper and it's shown he does sincerely respect Captain Queenan.
  • When Sullivan suggests to Ellerby that Queenan was killed by the undercover officer, Dignam, knowing Costigan would never do such a thing, immediately dismisses this as a lie.
  • The script explicitly notes that beyond avenging Queenan, Dignam executes Sullivan to avenge Costigan as well, whom he didn't even like.
• Politically Incorrect Hero: During his very first scene he drops the n word and "cunt".
• Sincerity Mode: Drops his profane act a few times, for instance telling Costigan early on that he's too smart to be a cop and telling him that the police really do need him for the undercover role.
• Sir Swears-a-Lot: Everybody swears in the movie, but he himself hardly says a sentence without a swearing word.
• Tranquil Fury: He says not a word when killing Sullivan, but the hateful look on his face speaks volumes.
• Ultimate Job Security: His extensive undercover work and the fact that he seems to be a damn good cop are the only reasons he probably hasn't been fired, especially given how he blatantly insults Captain Ellerby who mostly just takes it in stride. That said, Ellerby does suspend Dignam after the latter assaults Sullivan, indicating that there are limits to how much his superiors are willing to put up with.
• Undying Loyalty: To Captain Queenan, who seems to be the only person he genuinely respects. He's not fond of Billy but will defend his cover to the end, as Colin finds out the hard way.
• Vigilante Man: He's a police officer, so he is generally isn't this and can enforce the laws. But at the end, when Sullivan manages to escape any legal consequences, he takes justice into his own hands and shoots him in his apartment.

Brown

Officer Brown

Played By: Anthony Anderson

An officer who trained along with Billy at the police academy.

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• Boom, Headshot!: He's killed by Barrigan this way.
• By-the-Book Cop: When holding both Costigan and Sullivan at gunpoint and being unsure who to trust, he displays a little of this.
• Chekhov's Gunman: He returns in the final act as Billy's reinforcement to arrest Colin Sullivan.
• Henpecked Husband: Or at least hen-pecked boyfriend, as he comments that part of the reason he's finishing police training is because his significant other berated him for never finishing anything when he considered dropping out.
• Mauve Shirt: Thanks to Barrigan.
• Token Minority: The only African-American major character in the film.

Barrigan

Officer Barrigan

Played By: James Badge Dale

A police officer and a friend to Colin Sullivan.

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• Asshole Victim: Considering he is betrayed and murdered by his friend Colin right after he just murdered Costigan and Brown without hesitation, it's hard to feel bad for him.
• Bitch in Sheep's Clothing: Introduced as an honest cop, unaware of his partner Sullivan's corruption. He is just as crooked as Sullivan, if not worse.
• Boom, Headshot!: He unexpectedly kills Billy Costigan when the elevator opens and saves Colin. Then Colin grabs a gun and kills Barrigan the same way.
• Chekhov's Gunman: Plays a massive part in shaping up the ending, killing Billy Costigan and revealed to be another mole for Costello.
• Detective Mole: Just like Colin, he was working for Frank Costello to spy on Sullivan himself.
• Dirty Cop: He was working secretly for Costello, much like Colin.
• Even Evil Has Standards: It appears that he was genuinely trying to save Sullivan at the end of the film, perhaps because he was the only other surviving member of Frank's gang.
• Hero Killer: Murders Costigan and Brown.
• The Mole: Implied to have been placed on the police by Costello to spy on Sullivan.
• The Scapegoat: Sullivan pins all of his crimes on Barrigan after killing him.
• Too Dumb to Live: Given the chronic backstabbing that was going on in Costello's gang and the fact that he knew Costello had planned to sell them out to the FBI, Barrigan really should have known better than to assume Honor Among Thieves with Sullivan.
• Walking Spoiler: He is spying on Colin on behalf of Costello.

Costello's Gang

Frank Costello

Francis "Frank" Costello

Played By: Jack Nicholson

A ruthless and infamous old mobster targeted by the Massachusetts State Police.

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• Asshole Victim: Racist, constantly unpleasant, and a mob boss. The only people sad to see him go are the FBI.
• Ax-Crazy: Established early on when he and French execute a man and woman on a beach.
  Costello: Jesus... she fell funny. (starts chuckling)
  Mr. French: Francis, you really should see somebody.
• Bad Boss: He constantly threatens to murder his underlings if they displease him. He kicks it up a notch at one point with Sullivan, threatening to have his girlfriend raped if he doesn't find the mole. Costigan also mentions that he doesn't pay much.
• Beard of Evil: Frank is an slovenly, unshaven bastard of a mob boss.
• Big Bad: All these infiltration games are centered around him and his mob. Also, he corrupted a very young Colin Sullivan to join him into his mob and uses him as a mole inside the police.
• The Charmer: Frank is very charismatic and skilled at gaining loyalty.
• The Corrupter: He tricked Colin to join his mafia when he was just a kid.
• Chronic Backstabbing Disorder: Frank is betraying his own men to the FBI, taping Sullivan so he can give him up if the need arises, and screws the Chinese government over on a deal for stolen missile technology.
• Cool Shades: He wears them on occasion. Comes with being played by Jack Nicholson.
• Dirty Coward: For all his bravado, he's willing to sell out his entire crew to avoid jail.
• Dirty Old Man: In his first scene, he hits on a teenager by asking if she's had her period yet. Later, he makes a pass at a nun.
• The Don: Has been the head of his own gang for decades, and is the most wanted organized crime figure in Boston.
• The Dreaded: Everyone, particularly his own men, is scared shitless of Frank and with good reason.
• Evil Eyebrows: A trademark of Jack Nicholson.
• Evil Old Folks: Age has not slowed down his rampant criminal activities, nor has it made him any less intimidating.
• Expy: Of Irish-American mobster James "Whitey" Bulger.^note There was a real-life Italian-American mob boss named Frank Costello (the surname is found among both Irish and Italians), but he didn't have much in common with the character other than the name.
• Faux Affably Evil: He comes across as a charismatic guy for at most, a few seconds, before revealing what a depraved psychopath he truly is.
• For the Evulz: The reason he truly does what he does. At his core, Frank is a sadist.
  Billy: You don't need the money.
  Costello: I haven't "needed the money" since I took Archie's milk money in the third grade. Tell you the truth, I don't need pussy any more either... but I like it.
• Horrible Judge of Character: There's loads of evidence that Billy is a rat, and Costello says so from the beginning. He ends up trusting Billy more than anyone else who worked for him.
• Hypocrite: Costello is homicidally obsessed with snuffing out the rat in his crew. This makes it all the more ironic when he is revealed to be an informant for the FBI, selling out every member of his crew, including his informants in the police like Sullivan.
• The Informant: He is actually informing the FBI and it's the reason why the Massachusetts State Police and the Boston Police can't arrest him for his crimes.
• The Irish Mob: He leads his own Irish-American crime syndicate.
• It's All About Me: It becomes clear that Frank Costello only has loyalty to himself alone. This is proven when he's revealed to be an FBI mole compiling information on every one of his crew, including Colin Sullivan to whom he acts as a Parental Substitute. And taken further when he quickly leaves his trusted Number Two Mr. French to die in a car fire during the sting operation.
• Kavorka Man: Not much to look at in his later years, and that's not even getting into his personality but he has no issue attracting beautiful women.
• Large Ham: Jack Nicholson explodes any piece of charisma and presence to his performance and chews almost every scenery like a rat.
• Meaningful Name: The historical Frank Costello, an associate of Lucky Luciano and eventual leader of the Genovese crime family.
• Morality Pet: Billy is one, of sorts. Costello trusts him more than anyone else in his crew, and in one scene he even suggests that Billy consider getting an education. He might've thought that Billy had the smarts to become his mob lawyer, but he shows clear respect during this conversation.
• No Historical Figures Were Harmed: His character is heavily inspired by Boston gangster, Whitey Bulger, who both had an informant in the FBI and was an informant himself.
• Politically Incorrect Villain: Some of his snarky comments are filled with lots and lots of black humor, whose targets includes black people, Asians and pedophile priests. Also, he slept with a nun and flirts with a teenage girl.
• Properly Paranoid: For as crazy as he is about it, he's not wrong about there being a cop in his crew. Possibly more than one if you include Delahunt.
• Sanity Slippage: As Costigan tells Queenan, Costello seems to get crazier as the rumor of the mole is intensifying. One scene involves Costello coming to the pub's bar with his arms covered in blood and acting like normal, telling his men to clean the mess he left.
• Shadow Archetype: He's this to Costigan. They are both highly intelligent, hot-blooded, have similar thoughts and ideas, and are both secretly informants. He is essentially what Costigan would eventually become if he never left the mob. This is even implied by both Costello and Costigan at one point.
  Frank: Do you wanna be me?
  Costigan: I probably could be you, yeah. I know that much. But I don't wanna be you, Frank. I don't wanna be you.
• The Sociopath: Murders, tortures and stabs people in the back without a care in the world. At one point, he casually pulls out a severed hand in a plastic bag while having a private chat with Costigan over lunch.
• Stupid Evil: He switched out the microprocessors for fakes when he tried to sell to the Chinese. If they hadn't been arrested, Costello would probably have had to put up with a gang war for screwing them over.
• Villainous Breakdown: When he finds out about Delahunt (possibly) being a cop.
• Villainous Friendship: Seems to have one with Mr French.
• Villain Respect: Never to known cops, but he admires several members of the Costigan family.
  • He knew Costigan's father, and seems to hold him in a certain esteem, despite the fact that Willam Costigan Sr. refused to work for Costello.
  Costello: There's a man coulda been anything.
  Costello: You know, if your father were alive, and saw you here, sitting with me, let's say he'd have a word with me about this. In fact, he'd kill seven guys just to cut my throat, and he could do it... He kept his own counsel. He never wanted money. Can't do anything with a man like that.
  Costello: Your Uncle Jackie, he also would kill my entire fuckin' family if he saw me here with you.
  • He treats Billy far more respectfully than he does Colin, despite Billy's being a new recruit while Colin had served Frank since childhood.
• Wicked Cultured: He goes to an opera play, along with two of his lovers. He apparently enjoys it as he quietly shushed one of his girls. He also seems to enjoy drawing, and is fairly good at it.

Mr. French

Mr. Arnold "French"

Played By: Ray Winstone

Costello's most trusted enforcer.

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• Beard of Evil: A small goatee.
• Better to Die than Be Killed: He ends up committing suicide after getting himself trapped inside the car.
• Deadpan Snarker: He's quick with a witty remark.
• The Dragon: To Costello.
• Exact Words: French isn't gonna hurt ya. He's gonna kill you.
• Genius Bruiser: He's powerful and tough, but he's no idiot. He makes plenty of decisions for Costello's organisation.
• Til Murder Do Us Part: It is revealed in a flashback that he killed his wife (presumably because of infidelity).
  French: But she got reliable.
• Villainous Friendship: Has a genuine one with Frank, it seems.
• What the Hell Is That Accent?: Wherever French's supposed to be from, it most certainly isn't Boston, or even North America for that matter.
  • His actor is English (London to be specific). It’s possible French is meant to be Irish-British.

Fitzy

’Fitzy’ Fitzgibbons

Played By: David O'Hara

A slightly dim but intimidating henchman of Costello.

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• Actually Pretty Funny: He can't help laughing when Costello is yelling at him about dumping a body.
• Boom, Headshot!: Shot in the head in a gunfight with Boston police.
• The Brute: His primary role in Costello's organisation.
• Dumb Muscle: He's not very smart, as evidenced by his inability to successfully hide a body.
• Hero Killer: He's part of the group that kills Queenan.
• Villainous Friendship: Fitzy has a genuine friendship with fellow thug Delahunt.

Delahunt

Timothy Delahunt

Played By: Mark Rolston

One of Costello's top thugs.

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• Affably Evil: He's pretty friendly with the rest of Costello's crew, though he may or may not be an undercover cop and thus not evil at all.
• Ambiguous Situation: After his body is found, the news reports that he was an undercover cop who infiltrated Costello's gang. Fitzy and the others buy into this, but Costello is convinced that he was labelled as such so that he will think there is no longer a rat in the crew. Which makes sense, since there is still a rat in the crew: Costigan. It's never stated which is correct.
• Dumb Muscle: Seemingly, as he's on the same level as Fitzy.
• Hidden Depths: Revealed as he's dying, when he speaks to Costigan.
• I Never Said It Was Poison / Dying as Yourself: Delahunt figures out that Costigan is an undercover cop because he is at the place where the other gangsters were congregating to catch the mole, even though Costigan was accidentally given the wrong address.
• The Mole: He's actually an undercover cop. Possibly.
• Undercover Cop Reveal: He's actually an undercover BPD officer. Or perhaps not - Costello seems to think this is a ploy.
• Villainous Friendship: He and Fitzy are friends.
• Wham Line: His last words.
  Delahunt (to Costigan): Tell me why I didn't tell nobody.

Other Characters

Madolyn

Dr. Madolyn Madden

Played By: Vera Farmiga

A psychiatrist who Costigan sees under the terms of his probation.

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• All Girls Want Bad Boys:
  • Averted. Madolyn does not know anything about Colin being a mole and when she discovers it she refuses to speak to him for the rest of the film and is implied to have sent the tapes implicating him to Dignam.
  • Played with in the case of Billy. With his troubled personality and violent behavior, he seems like more of a bad boy by comparison. In reality, he is way more noble and heroic than Colin.
• Alliterative Name: Madolyn Madden.
• Babies Ever After: She becomes pregnant, with both potential fathers dead. Though it's strongly implied that Costigan is the real father.
• Composite Character: From the original, Ming's wife, Yan's psychiatrist, and Yan's ex-girlfriend (as well as the mother of his child) are combined here for Madolyn.
• Love Interest: For Sullivan and Costigan.
• The Shrink: She's a psychiatrist who treats both Sullivan and Costigan.
• The Smurfette Principle: The only major female character.

Sean Costigan

Sean Costigan

Played By: Kevin Corrigan

Billy Costigan's cousin.

• Momma's Boy: Still lives with his mother.
• Put on a Bus: Vanishes from the plot after Billy is accepted for work with Costello.
• Stupid Crooks: Gets no respect from any of the bigger crooks besides what little his family name buys him, and doesn't seem that savvy in the one operation he's shown conducting with Billy.
• Thicker Than Water: He's a little surprised/suspicious when Billy asks to do a deal with him, but is pleased by the idea, and kind of happy to see him.

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