This is what happens when I can't sleep.
I dearly love Martin Scorsese's The Departed. A film of so many layers, so many different tics and easily-missed traps, every word of dialogue, every facial expression needs to be seen again and again in order to get the full richness of Scorsese's story.
One of the things I take away from this film is its depiction of contingency. In a perfect world, or at least one far better than the one we inhabit, Matt Damon's character, Colin Sullivan, would never have made it through to become a police officer; Leonardo DiCaprio's Billy Costigan would have been the shining white night, rather than the one Mark Wahlberg's Dignam abuses and sends out as an undercover agent in Boston's southside Irish mob. Since it depicts certain moral realities of our world, however stylized, we are confronted with the aggravating complications of radical contingency.
Keeping it as short as possible, what I mean by "radical contingency" in this case is the overlapping realities that limit our freedom, our ability to fully comprehend our world, and to make decisions that are completely moral. This goes for both individuals and institutions. If there were truly a moral law, quite apart from there being no need for a police unit dedicated to ending something like organized crime, the State Police would have recognized Colin Sullivan for what he was; would have investigated and understood his connection to Frank Costello. They also would have known that Billy Costigan was an upright, dedicated individual whose pursuit of a career as a police officer was due in no small part as penance for his family's connection to Boston's underworld.
Keeping in mind that we never know all that we think we know; that our decisions are never as fully considered as they could or should be; that our freedom of decision and movement in life is limited by forces outside ourselves, institutional and otherwise, that are themselves limited, contingent, and flawed. This is what makes for the drama in this film; this is also what makes the film's characters so effective.
Yet, it is also what makes it so morally aggravating. There is a moment in the film when "what might have been" becomes so crystal clear, all these questions rise up and force themselves on the viewer. In the moment when Billy and Sullivan's therapist girlfriend, Madolyn Madden (played by Vera Farmiga), make love, we see how easily, how smoothly, how utterly better the world could be. These are two people who could have found each other under different circumstances, made a life together without duplicity and obfuscation. The ease of their relationship, compared to the awkwardness of Madden's relationship with Sullivan (combined, as it is, with the reality that he is a criminal playing cop), the passion between Costigan and Madden (compared to Sullivan's sexual dysfunction) makes as clear as day what might have been.
I do not know if there is a lesson one can take away from these reflections. Is it, perhaps, that even a moment, just a moment, of real love and "vulnerability" (Madden's description of Costigan just before he kisses her) sometimes has to be enough, but can perhaps be enough? Is it, on the other hand, that we should live our lives understanding that we can never have enough information, never enough trust in our own freedom of action and decision? Is it even, perhaps, that those to whom we are closest, no matter how much we may think and believe otherwise, are not at all the people we believe them to be? All these lessons? None?
All I know for sure is that one moment of honesty and tenderness in a film filled with brutality and lies offers the briefest of breezes of what might have been through the dark landscape of what is.