Martin Scorsese’s “The Departed” is one of his best films. The 2006 Best Picture winner features an ensemble of incredible actors and wonderful storytelling. However, there are many scenes that are up for interpretation. For instance, what’s in the package Billy gives Madolyn during their last encounter?
After Billy (Leonardo DiCaprio) finds out that Mass. State PD Officer Collin (Matt Damon) is mob boss Frank Costello’s (Jack Nicholson) rat, he goes on the run. However, before he disappears, Billy visits his therapist and lover, Madolyn (Vera Farmiga). Billy hands Madolyn a manila envelope and instructs her to only open it if he’s dead or calls her and tells her to open it. Madolyn writes “Costigan” on the envelope and puts it in her drawer.
The film’s next scene causes some confusion because it features Madolyn opening a different envelope that’s also from Billy. Billy sends Collin a white envelope containing tapes of Collin’s conversations with Frank. However, it was unbeknownst to Billy that Collin and Madolyn are dating and living together. Madolyn listens to the tapes and essentially breaks up with Collin.
Later, Collin meets Billy on a rooftop where Billy arrests Collin for his crimes. Trooper Brown (Anthony Anderson) arrives, per Billy’s invitation, but misinterprets the situation. Brown instructs Billy to drop his gun and release Collin. Billy’s next lines reveal crucial information as to what’s in the manila envelope he gave Madolyn.
Billy gave Madolyn the evidence that incriminates Collin because no one would suspect there’s a link between the two. That way if Collin or anyone from Costello’s mob kills Billy, the evidence will still be out there. Furthermore, the envelope most likely also contained instructions to give the evidence to Dignam (Mark Wahlberg). The is evident when Dignam appears in Collin’s apartment to kill him in the final scene.
While the only two people who know for sure what’s in the manila envelope are Martin Scorsese and screenwriter William Monahan, our analysis is that it’s incriminating evidence against Collin.