NOTE: This spoiler was submitted by Jeremy
Jim Bennett (Mark Wahlberg) is sitting by his grandfather Ed (George Kennedy), who is lying on his deathbed. Ed asks Jim what he'll be worth in this world when he's leaving him with nothing. He leaves Jim with the thought that now he has become just like his grandfather during his own adult life.
After Ed's funeral, Jim goes to a casino. He spots a young woman (Brie Larson), who looks at him with a bit of surprise. Jim goes to deal his cards, and he ends up losing money. He is approached by a loan shark named Neville Baraka (Michael K. Williams), who comments on his losses. Jim owes $240,000 to a man named Lee (Alvin Ing), who runs an underground casino ring. Jim borrows $50,000 from Neville and gives $40,000 to Lee while he takes the rest to try and win more money back. This plan fails, and Jim is given seven days to pay back the debt or he's dead meat.
Jim teaches English literature at college. He's giving a lecture on Shakespeare and he calls out one student, Dexter (Emory Cohen), who is a tennis player that doesn't apply his talents because he is actually good, but because, according to Dexter, of his desire to join the tennis team because the tennis players had really good weed. Jim also calls out Amy Phillips, the young woman from the casino, and says she is the best writer in the class and thinks of her as a prodigy, but wonders why she chooses to sit in the middle of the class instead of the front where she belongs.
Jim visits another loan shark named Frank (John Goodman). He is willing to loan Jim money, but only if he tells Frank that he is not a man. Jim refuses to do so and he leaves.
During one of his classes, Jim calls out a student named Lamar Allen (Anthony Kelley), who is texting during class. He makes Lamar stay after, and they discuss Lamar wanting to be a professional basketball star. Lamar is currently the star player on the college basketball team, but Lamar wants people to see him for more than what is expected of him.
Jim's mother Roberta (Jessica Lange) catches him in the tub watching one of Lamar's games and asks him if he put money on the game. She tells Jim that she got a call from a gangster asking for money. Although he refuses her help, she goes with him to the bank and takes out the money needed to pay off his debt. Roberta gives Jim the money, and they part bitterly.
Amy drives up by Jim while he sits at a bus stop and invites him in the car. He goes with her and they spend the day together, semi-romantically. She learns what a messed up person he is, while he admits to her that he does want to be happy and that he has desires in his life. They later go to the casino, where Jim plays with Roberta's money and loses every last bill.
Jim spends what little time he has left drinking away his sorrows and trying to pawn off his watch. After he unsuccessfully tries to make a negotiation, Neville and his goons abduct Jim. They bring him to an empty building where Neville gives Jim his last option. Since Neville knows about Lamar and his talent on the court, he tells Jim to convince the boy to win a game by a margin of seven points or less, or else Neville will kill Amy.
Jim approaches Lamar and tells him he'll get $150,000 if he goes along with the scheme. Later, Jim goes to meet with Frank again at a bar. Frank tells Jim that much of the accomplishments in the country and most of the world are won by having a "fuck you" attitude towards life. With this approach, Jim can go on living a little easier. Frank then lends Jim $260,000 to wager in the game.
Jim then pays Lee a visit and demands that he stake him. Lee's thugs assault Jim, but Lee eventually agrees to stake Jim $150,000.
The day of the basketball game comes, with Neville and his boys watching on TV while Jim sits in during the game. Lamar starts off excellently, making Neville think something is wrong, until Lamar starts to play poorly and gets himself benched. After a while, Lamar is brought back into the game, and he succeeds in winning the game while still shaving points. Jim finally manages to pay Neville back and is relieved to never have to see him again.
Jim then convinces Frank and Lee to come together at an underground gambling den. He puts in all his money on black to play for the two men. After a spin, the ball lands on black, and Jim's debt to Frank and Lee is gone. He leaves the den, declaring he is not a gambler, and Frank follows him in his car. Frank offers Jim overpayment since Jim gave Frank more money than what was owed, but Jim replies, "Fuck you". Jim runs all the way through the city as the morning comes until he gets to Amy's apartment.