How we cite our quotes: All quotations are from The Departed.
Quote #1
DIGNAM: So you have family connections down in Southie, right? Through your father? Why don't you tell us about your Uncle Jackie?
Dignam knows all about Billy's Uncle Jackie, who was a big-time mobster in the tough neighborhood of Southie. But rather than hesitating at this, Dignam hopes he can use this to help insert Billy as a believable police informant.
Quote #2
DIGNAM: You got quite the family tree. That maggot uncle of yours... Tommy Costigan is another goof. He gets busted selling guns.
Yup, it looks like Billy's uncle Tommy was caught selling guns. In fact, it seems like it's hard to find anyone in his family apart from his dad who isn't (or wasn't) a career criminal.
Quote #3
DIGNAM: Family's all criminals except for the old man, huh?
The short answer to this question is yes. All members of Billy's family on his father's side are criminals except for his dad. This is in pretty stark contrast to Billy's mom's family, which seems made up of a bunch of rich New Englanders—whom Billy hates.
Quote #4
DIGNAM: F***ing family's dug into the Southie projects like ticks. Three-decker men at best. You, however, grew up on the North Shore, huh?
Dignam knows that Billy is from a rough neighborhood. But so is Dignam, and he's not going to let Billy forget the fact that the kid grew up with his mom in a much more posh part of Boston. Dignam was born and raised in Southie, and he's not about to let some poser from the North Shore say the same thing.
Quote #5
DIGNAM: Tell me, what's a lace-curtain m*********** like you doing in the staties? Well, families are always rising or falling in America, am I right?
So Dignam's question is this: why would someone from a good background like Billy try to be in the police force when he could be a doctor or lawyer? There's something fishy about the whole thing, and Dignam doesn't want Billy joining the police just to prove how tough he is.
Quote #6
UNCLE EDWARD: What's this I hear from Stephanie about you becoming a policeman?
BILLY: Stephanie, who was the only one who came to my father's funeral?
It's pretty clear that Billy doesn't think much of his mother's family, especially since most of them didn't show up at his father's funeral. He more or less accuses them of abandoning his father because they thought they were too good for him, and it looks like he'll never forgive them for it.
Quote #7
UNCLE EDWARD: Trying to prove something to the family?
BILLY: When you say "the family," who do you mean exactly? You?
Billy finds it almost comical when his uncle talks about "the family," since Billy doesn't even come close to thinking of this guy as family. In his mind, Edward is just a rich jerk who doesn't get it and never will.
Quote #8
MR. FRENCH: I f***ing know you. I know your family. You make one more drug deal with that idiot f***ing cop-magnet of a cousin of yours, and I'II forget your grandmother was so nice to me.
Even the psychopathic Mr. French knows the value of knowing someone's family. You see, Billy's grandmother was nice to Mr. French when French was just a little boy. And this is reason enough for French not to kill or beat up Billy for doing drug deals on Costello's turf.
Quote #9
COSTELLO: Your Uncle Jackie, he also would kill my entire f***ing family if he saw me here with you.
Costello knows full well that Billy's uncle wanted something better for him than a life of crime. And he knows that Jackie was a tough enough dude to come after him if he were alive to see him pulling Billy into a life of crime.
Quote #10
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...
Costello might think Billy's father was a nobody for working at the airport all his life, but he does have a deep respect for the man's toughness and independence. He also knows that he's doing a bad thing by corrupting the old man's son, and he even has enough of a conscience to worry about it from time to time.