Things About The Departed That Don't Make Any Sense

This year is the 15th anniversary of Martin Scorsese's crime thriller The Departed, and by now most can agree that it's not just one of Scorsese's best movies, but one of the best movies of this century, period. The Departed took home four Academy Awards in 2007, including Scorsese's first and only Best Director win, so it's not exactly underappreciated.

But even the greatest movies can still have moments that don't really hold up under close scrutiny. In practically any story, there will always be flaws: a handful of plot holes, details that are internally inconsistent, or characters behaving out of character. There's no such thing as a perfect story (other than the exception that proves the rule).

The Departed is actually a remake of the 2002 Hong Kong thriller Internal Affairs, and like that film, the story centers around two moles on opposing sides of a law enforcement operation. In The Departed, Billy Costigan (Leonardo DiCaprio) is a police officer who infiltrates the mob, while Colin Sullivan (Matt Damon) is a mob informant who's infiltrated the police department. 

It's a lot of fun to watch, but anyone who's expecting a realistic portrayal of undercover police operations should probably look elsewhere. Here are three moments in The Departed that make less and less sense the more you think about them. 

Midway through the movie, mobster Frank Costello (Jack Nicholson) realizes the police have a rat inside his operation, so Sullivan tries to figure out the rat's identity by having his boss, Captain Queenan (Martin Sheen), tailed. Costello's goons follow Queenan to a meeting with Costigan, and Costigan escapes before Costello's men see him, but Queenan isn't so lucky. Costello's men toss him off the roof of a building to his death. 

It's a devastating moment for Costigan, because Queenan was one of the only people in the MSP who knew of his mission and had the power to protect him. But hardly anyone else seems to notice, either within the MSP or the greater Boston Area. There's no apparent media coverage, no public outrage, no escalated police response, nothing. 

Yes, Frank Costello is himself an FBI informant, which does offer his operation some degree of protection, but if organized crime murdered a high-ranking police official in a major American city in broad daylight, it would be a Very Big Deal. Even the FBI couldn't protect Frank from that much blowback. At the very least, you'd think having a police captain murdered would be enough to bring Frank in for questioning, but nope; not in The Departed. 

According to Reddit, one of the biggest fan complaints about The Departed's logic is that the identities of both moles really wouldn't be too difficult to figure out. Take Colin Sullivan, Costello's mole in the Massachusetts State Police. It just so happens that Sullivan is from the same neighborhood as Costello, but nobody at the MSP seems to notice this. 

It's odd that nobody really suspects that Sullivan is the mole. Costello is a mobster, and like many mobsters, he works locally. He's spent years taking control of the neighborhood of South Boston, extorting businesses for protection money and controlling all the illicit dealings in the area. When it comes to recruiting new members for his organization, while Frank does bring in outsiders (Patrick Fitzgibbons is Irish, for example), most of his henchmen come from Southie — like Sullivan. An early flashback in the movie shows the exact moment when Frank began grooming a young Colin to be his mole. 

Queenan and Dignam (Mark Wahlberg) run the Special Investigations Unit that handles Costigan, and they're already aware Costello has a mole inside the MSP before they send Costigan on his mission. They also know that mobsters usually recruit from their own neighborhoods. Colin Sullivan just so happens to be an MSP official from Costello's neighborhood, who has access to all the SIU's intel on Sullivan. All those coincidences didn't set off any alarms?

To be fair, Sullivan does have a clean record as a police officer, and Dignam does accuse Sullivan of being crooked after Queenan's death. But Sullivan's angry defensiveness is apparently enough to satisfy Dignam's suspicion — at least until Costigan winds up dead. Dignam might want to be a bit more proactive next time.

It's not just the MSP who need to brush up on their rat-catching skills. Frank Costello probably should have been able to figure out Billy Costigan was working for the police.

The MSP give Costigan a cover story that includes real jail time to convince Costello and his men to welcome him into their operation. As gangsters, Costello and his men are naturally suspicious of newcomers — especially ones they don't know. In one memorable early scene, Costello removes Costigan's arm cast and beats his broken arm with a shoe, demanding to know whether he's a cop. Costigan manages to pass the test, but this scene establishes Costello's skepticism.

Later in the movie, the MSP and FBI attempt to bust Costello's illicit microchip deal with a Chinese gang. This makes Costello realize he must have a mole. Logically, he accuses the new guy, but Costigan manages to convince him otherwise. Take a closer look at the scene where the deal with the Chinese gang goes awry. There are only five people in Costello's organization who know the deal exists: Costello himself, Frenchy, Delahunt, Fitzgibbons, and Costigan. That leaves four possible suspects besides Frank for the mole's identity.

Later on, when Sullivan tips off Costello that Queenan is meeting with his mole, Costello receives the call in a bar where Frenchy, Delahunt, and Fitzgibbons are also present. The only person not in the bar? Costigan, which leaves him as the only person who could be the mole.

It's not like Costello takes great care of himself. Maybe those years of substance abuse haven't been kind to the brain that handles strategic thinking.