FLASHBACK: The movie begins as Montgomery "Monty" Brogan (Edward Norton) is driving in NYC with Kostya (Tony Siraguza), his Russian/Ukranian mobster-type muscle. Kostya has a heavy accent and some trouble with English idioms. He references "Doyle's Law" rather than Murphy's Law. They're late to meet with some "important people." They find a badly injured dog that was obviously abandoned after a dogfight, and Monty wants to first shoot the dog with Kostya's gun (as a mercy killing) and then when he sees what a scrapper the pup is, he decides to save the dog. He grabs it in his jacket, and sticks it in his trunk, and though the dog bites him, he's very impressed with that fighting spirit. They drive on.
PRESENT: Monty is sitting at the pier with the dog, whom he named Doyle. It's early morning; people are jogging. A strung out junkie comes to Monty begging for a fix, and Monty tells him to go to Harlem, because he's been "touched" and is out of the business. The junkie just doesn't seem to get it, says he's been coming to Monty for 5 years and that he'll remember this! He lurches off, and Monty wanders away with Doyle.
Monty and Doyle walk along the streets of NYC, and end up on the campus of what looks like a private prep school. Monty stands looking at a display of sports trophies and old photos, til a school administrator confronts him and tells him to leave with the dog. He tells her that he used to go to this school, and was on the basketball team, was doing well til he was kicked out of the school for fighting. She thaws a little bit as he shows her himself in the photo and says he held some big record. She tells him that record was broken just last year, and she knows because she coaches the girls' team. He's a little taken aback/wistful. He asks if she could help him find Jake Elinsky, his friend.
In a classroom, Jakob "Jake" Elinsky (Philip Seymour Hoffman) is teaching his poetry class. The chairs are all arranged in a circle and Mary (Anna Paquin) who is dressed very provocatively, and has a giant henna tattoo on her stomach, is reading a poem out loud.
The rest of the class seems like they're completely dead/disinterested. Just then, Monty shows up at the door and briefly talks to Jake. He tells him to get in touch with Frank and that they can't meet for dinner because he has to go see his dad. That they should meet afterwards at a bar and then there's a "going away" party for him that night at the Bridge club. He notes that Mary is hot and that she's giving him the eye. He leaves and the bell rings; the students all scatter.
Then I'm not quite sure I remember the exact order that this all happens in the next section, but basically all these things happen.
* We see a busy stock/bond exchange type room. Francis "Frank" Xavier Slattery (Barry Pepper) gets the call from Jake. He can't talk though, and hangs up. Frank's boss comes and yells at him that he needs to sell off some stocks/bonds. It's obvious that Frank has a very high pressure job and deals with a lot of money, but is on top of it all. He doesn't do what the boss asks and fights with some underlings. It looks like he was right not to sell the bonds, however.
* Back at the school, Mary comes to see Jake in the teacher's lounge. He asks about her henna tattoo and she implies that her mother doesn't really care what she does. Mary argues about the unfair B- grade that he gave her on her last assignment, saying she needs better grades to get into college. She's pissed he gave another student an A+ for a story about his dead grandmother, but the night before the funeral, that guy was getting drunk at a basketball party and slapping girls' asses. Jake says that it's sometimes difficult for guys to show emotion, and refuses to give Mary a better grade. She storms out.
* Monty and Doyle go home. Out on the stoop, Naturelle (Rosario Dawson), Monty's girlfriend, is waiting for him.
She's been sitting there all day, worried when he was already gone when she woke up. He says he needed to get out. It's obvious that there's a lot of tension between them. She wants to know if they're going to spend any time together or what. He tells her about the party being thrown tonight for him by Uncle Nikolai, and she really doesn't want him to go, but he says he can hardly avoid it. She then has him open a jar of honey, and she eats it straight out of the jar with a spoon, which he calls disgusting, but then they kiss. She wants him to take a bath with her, and he refuses, saying maybe later.
Then there's a FLASHBACK -- they're in the bath together, joking around about having kids and Monty teasing Nat for getting a tattoo of the Puerto Rican flag when she's lived her whole life in NYC.
Someone's at the door, and Nat thinks it's her mom. But when she opens the door, it's the DEA! The DEA agents are really pretty nasty. They treat both Monty and Nat rudely, and it's obvious they know where the drugs are hidden. One of the agents opens up the couch cushions, taking out a bunch of money and drugs. Monty's fucked.
Flash to the present, and Monty's sitting on the couch. Naturelle keeps bugging him about spending time together, and he tells her that she needs to be quiet. That he has to go see his dad and that he'll see her at the club later. He asks her to wear the silver dress, because that's how he wants to remember her. Then he gets dressed and takes off, leaving Doyle at home.
Outside, Kostya is waiting at the stoop and reminds Monty about the party being held tonight by Uncle Nikolai in his honor. Monty's wondering why people keep insisting he go to the party. He says he'll be there with Naturelle and some friends. Kostya says he shouldn't bring Naturelle, and implies that she's the one who ratted him out. Evidently, that is what everyone believes. Monty goes off to have dinner with his dad.
We next see Monty inside Brogan's, an Irish pub owned by his dad, James Brogan (Brian Cox). It's basically a fireman's hangout that has taken quite a hit in terms of business since 9/11.
During their conversation, we discover that Monty's dad used to be a fireman and an alcoholic. His mom died when Monty was only 11, and James blames himself for how things have turned out. "You could have been anything! A lawyer, a doctor!" It also comes out that James evidently owed money to some guy named "Sal" and Monty's been paying it off. "Where did you think that money came from? You didn't have any problems taking it," says Monty, and goes to take a leak.
There's a really powerful scene in the bathroom as Monty looks in the mirror and sees that it's got "Fuck You" written on it. Monty begins to rant about just about everyone in New York, the blacks, the Koreans, the Jews, the Russians, the Italians, the Irish, etc. as a montage shows clips of various ethnicities and places in NYWC. He curses out his friends Frank and Jake, he curses out Naturelle, and in the end, he says, "Fuck you, Montgomery Brogan, you had it all and you threw it all away." His rage is palpable. He tries to wipe the "Fuck You" off the mirror, but it's painted on.
He returns to the table and asks his dad if he trusts Nat. He says it's been weird and he's not sure, maybe she's the one that fingered him. He says he only really trusts his dad and Frank and Jake, his two oldest friends. He leaves to go meet Frank and Jake, and his dad says he'll come in the morning to drive him to the jail.
* There's another FLASHBACK to when Monty was taken in by the DEA. Naturelle gets let go and the DEA agents also imply that she was the one that fingered him. They threaten Monty with a 15-life sentence, explaining that the Rockefeller Laws in the state of NY make possession of that much drugs a major felony, and if he doesn't cooperate... They basically try to get him to sell out Uncle Nikolai, but he refuses and talks smack so it seems like they're going to throw the book at him.
* In the meantime, Jake has come over to Frank's apartment, which overlooks Ground Zero. The two men talk as they look down at the horrifying sight. Frank says that he has no intention of moving. The two men then discuss Monty. Jake seems to think that after Monty gets out, they'll still be friends, but Frank tells him that it's going to be over. That Monty's not really going to survive prison and they'll never see him again. That Monty was a drug dealer and this is his fault that it ended up like this. We find out that when he was kicked out of the private school as a teenager (he was there on scholarship) it wasn't for fighting, but for selling weed to the other kids. Jake wonders what will happen to Doyle and wishes that Monty could take his beloved dog into jail with him.
The two men then go over to a Chinese restaurant, where we find out more about the two. Frank tells Jake that Jake's in the 62nd percentile of all NY bachelors, while he, Frank, is in the 99 percentile. Criteria include the money he makes, whereas Jake (it turns out) has a trust fund and is ashamed of being a wealthy Jewish kid. Frank tells Jake that he also has chronic bad breath. Jake is really hurt by Frank's comments and points out that Frank has no table manners at all and he dyes his hair. As for Monty, he's in the 0 percentile. He's going to jail.
* At some point, there's another FLASHBACK where we learn how Monty met Naturelle. She's a high school student loitering in a playground where Monty meets up with a man in a suit (I'm pretty sure that it's the same guy as the strung out junkie in the beginning of the film), who gives him a number to call. Monty, however, borrows Nat's lighter to burn the number. They start chatting and he asks if she's 18, which she says he is. She's also on the basketball team and they flirt a lot.
* Now we cut to a bar where Frank and Jake are waiting for Monty and still talking about the percentile thing, which the cute female bartender is aware of. Haltingly, Jake starts telling Frank about his "friend" the teacher who has the hots for a student. Frank, naturally, sees through this, and gives Jake a hard time, saying he better not have fucked her. That he should wait til she's out of school. Then Naturelle shows up, looking the bomb in a silver latex dress. They joke around a little, with Frank asking why it is that girls always cry after really great sex. Nat goes to the bathroom, and Monty shows up. The bartender chick serves them free drinks and invites them all to her birthday party that weekend; there's a horrible, awkward moment. They drink and then they all take off to the club where the "going-away" party is being held.
* There's a huge line to get into the club, but naturally they can get in through the back like VIPs. The bouncer out front gives Monty some tips about going to jail and to keep his head down. A really hot DJ is spinning tonight, some 17 yo kid named Dusk. As the gang heads toward the back entrance, Mary spies Jake and runs up to him. She wants to get into the club with her friends and Jake pretends to be into Dusk while she says she thought he'd be more into Barry Manilow. Monty has Mary go in, but not her friends.
Inside the club, champagne is served and Mary drinks it right down. She and Naturelle go and dance, while Frank goes upstairs for some special whiskey. Jake and Monty share a quiet moment, where Jake tries to make a toast and fumbles. Monty says, let's drink to Doyle. He says that the best thing that ever happened to him was saving Doyle and that Jake should have him now, because Nat's going to live with her mom, and Doyle hates Frank. Jake is happy, but really worried that somehow it'll get out that he brought Mary into the club.
Frank comes back and then Kostya shows up. Kostya says it's time to go see Uncle Nikolai and he, Monty, and Frank start going upstairs. Monty asks for 5 minutes alone with Frank. He tells Frank that he had all these thoughts of going straight and investing the money with Frank's help, but he got greedy. Frank basically tells him the opposite of the stuff he had said to Jake -- that Monty's a fighter, that he's going to be OK, that when he gets out, he'll be there for him and they can start an Irish bar together. That he's known Monty since age 3 and never once broken a promise to him. Monty says that is all true, but tomorrow is when he's really going to be in trouble -- when he goes to the jail and the pretty boy that he is, gets reamed out (literally) by all the other convicts. He says he has a plan that might buy him some time and he makes Frank promise to help. We don't see find out what it is, as it cuts away.
In the meantime, Mary comes back to see that Jake's basically asleep at the table. Mary's totally drunk and "had some E earlier." She's having a really good time, she really likes Nat, she starts to bump and grind against Jake. He asks her to keep all this quiet, she hints that he should raise her grade. Then she basically asks where's the bathroom, and goes up there (it's a very obvious come-on). Despite his better judgement, Jake goes up there and kisses her. It's a weird, awkward moment. She seems stunned. He leaves the bathroom without another word.
Meanwhile, Nat is at another bar with Frank. She asks him to look out for Monty tonight, make sure he doesn't hurt himself (which is an underlying theme -- they think he might kill himself to avoid going to jail). Frank's drinking shot after shot of whiskey and he and Nat get into a fight. Basically, he accuses Nat of ratting out Monty and blames himself for not stopping him on his downward spiral. Up until this moment, it seemed like Frank may have been actually the one to rat him out, but it because obvious that he loves Monty and didn't. He tells Nat that she hasn't worked an honest day in her life and that he never took any of the money. "Seven years from now, I'll be at the gate waiting for him, and you'll be married to money." She storms off. Jake comes and tells Frank he kissed Mary. Frank tells him to shut up and have another drink; that they can't leave yet because they have to be there for Monty.
Monty and Kostya in the meantime are shown into a room where Uncle Nikolai is sitting. Kostya's gun is taken by the other thugs and it's a really tense scene. Uncle Nikolai is a Russian mobster who tells Monty about his first time in prison -- he was 14 years old, just a little boy. But he came out a man. He tells him that Monty should find someone who's not being protected and beat the shit out of him, and that way seem like he's a little crazy, but still respectful of the right people. Then Nikolai and the henchment basically threaten Monty with his father's life. They know everything about his dad and imply that they could "take care" of James -- either way, either by helping him out, or by snuffing him out. Monty begs them to leave his dad out of it, he says he wants out. He wants nothing to do with it anymore. He says he knows that they pinched him to get to Nikolai but that he didn't rat him out, he swears.
There's a tense, tense moment where Nikolai points the gun at Monty. But then he says that he knows that Monty didn't say anything. But someone fingered Monty -- who was it? Only two people knew where he kept the drugs and money. Naturelle and Kostya!!! Kostya admits it was him! He says he "had no choice" as Monty basically holds the gun to his head. But Monty tells Nikolai to "do his own dirty work" and leaves without killing Kostya. Nikolai reminds Monty to "survive" and as the door closes, the other Russian mobsters are beating the shit out of Kostya and about to kill him.
Monty, Frank, and Jake leave the club to go home and get Doyle. Monty asks if they don't mind staying out a little later to do something. Monty goes into the bedroom, where Naturelle is sleeping. He tells her he's sorry how it's been; that he knows it wasn't her. She says she loves him. He says he'll come back. He, and Frank, and Jake all go out walking by the river with Doyle. It's sort of like the scene earlier in the movie.
Then they go into the park and Monty calls in his favor to Frank. He wants Frank to "make him ugly" so that maybe he won't get shafted on his first day of prison. Frank won't do it. They all start screaming at one another, and Monty tells Frank he knows he's wanted to slap some sense into him. Eventually, Jake gets in the middle, and Monty punches him. Then Frank starts to beat the shit out of him, and crying. It's a really powerful, visceral scene. Jake is able to get Monty back to his feet and he lurches back to home, where Naturelle is absolutely horrified to see him in this state. She tries to get him cleaned up and wants him to go to the hospital, but he refuses.
We see Frank sitting in the same spot by the river that Monty was earlier. Jake's walking with Doyle and gets some attention from a girl because of it.
Monty's dad shows up to take him to jail, and Monty reluctantly agrees to go. He tells Nat she should forget about him and live her life, though she swears she'll wait for him. She gives him ice for the horrifying injuries on his face, but he dumps it all out on his way down and gets into the car with his dad.
As they drive up the turnpike, his dad offers to just keep driving. "You'll lose your bar!" "What do you think matters to me more? The bar or my only son?" Over a montage of scenes of them driving out west, James tells Monty of how he can find some town out there in the desert, disappear, make a new life for himself. He'll never see him again, but he'll know his boy's ok. Eventually, maybe, Monty can be reunited with Naturelle, and they can have kids and someday, he can tell the kids about his earlier life and how close it came that this blissful life "almost didn't happen." We see this playing out -- them driving through the desert, them drinking a final shot of whiskey together, Monty getting a new ID, a new job, reunited with Nat, the kids, and everything.
And as the "almost didn't happen" is said in the voiceover, we cut back to the car and see that they're still driving up the turnpike towards the jail, as Monty doses in a stupor.