Bookies(2003)

SHORT VERSION:
After a bookmaking episode nearly puts Jude and Casey into an unsavory situation with the mobster Larry, Toby pays Larry a visit and makes a deal with him: Larry can pick the team and the game, and if he wins, then he and his friends will pay him $100,000 and quit being bookies, but if they win, then he must leave them alone and forget that any of their unpleasant experiences ever happened. Larry accepts the deal and selects a championship boxing match, with him betting on the challenger and leaving Toby, Jude, and Casey to bet on the champion.

However, the guys immediately figure out that the match will be fixed, so they liquidate all of their assets and bet heavily against the guy Larry gave them through another bookmaker. They win $400,000, and they give $100,000 of it to Larry as promised, then split up the rest between them and get out of the bookmaking business.

Afterwards, the trio’s friendship diminishes, but Toby rekindles his relationship with his love interest Hunter.

LONG VERSION:
One day, Jude (Johnny Galecki) comes back to his and Toby’s (Nick Stahl) dorm room high on cocaine and finds Hunter (Rachael Leigh Cook) there hanging out with Toby and Casey (Lukas Haas), and when he discovers that Toby had told her about their bookmaking operation, the two of them have a fight. Later, once they have calmed down, Toby tells Jude that he is worried about him, so they make a deal where Jude will quit cocaine cold turkey in exchange for Toby taking bets larger than $500.

The next day, Jude greedily accepts a $100,000 bet from the wealthy student Julius (Steve Hudson) that he places on a university basketball game between their university, Kingston, and his pick, Preston University. Though Jude tells Toby and Casey that the spread is ten points to Kingston and that Preston is no threat, he later goes behind their backs and bribes a few of the players on the Kingston team to cover the spread to ensure that Julius pays up. Hunter finds out about this and quickly informs Toby and Casey about it, and Larry (David Proval) and Vincent (John Diehl) – the mobsters who were once the guys’ bookies but whom they have now run afoul of for overlapping their business into their territory – gets wind of this as well as Jude’s name, so they have Julius pay the Kingston team even more money to shave the points in exchange for them erasing the debt he owes them. Hunter discovers the team’s plan to shave when she tells the team’s star player Duane (Zuri Williams) about Toby and his bookmaking operation and he responds by saying that his team isn’t covering the spread, so she calls Toby and warns him that he and the others will be getting screwed and it would be wise to call the whole thing off. Toby runs to the stadium and tries to convince Duane to cover the spread and even tries to bribe him, too, but Duane refuses him. He then calls Jude and tells him to get the bet cancelled, but he replies that it is too late to do that. Out of desperation, Toby calls Larry himself and tries to put $100,000 on Preston, but after Larry outs him as being a friend of Jude’s and an assistant in his bookmaking operation, Larry warns that they had better be able to cover for Julius’s debt because he and Vincent will be the ones collecting.

Luckily for the guys, Kingston wins by ten points, but when Jude calls Larry wanting to know if he is going to cover for Julius’s debt, he tells Jude that he is lucky that he doesn’t try to get revenge on him for this, and warns him and his other friends to not take any more bets or else there will be consequences. Feeling like they deserve the $100,000, Jude tells Toby and Casey that he is going down to Larry’s headquarters to get it, but Toby replies that he has lost his mind and soon tells him that he is done with being a bookie. He then visits Hunter and lets her know that the mob had tried to get him and his friends under their thumb and says that he is through with bookmaking, but she informs him that she doesn’t want to be around him anymore because he and his friends just took some very serious risks with the lives of other people instead of walking away, and encourages him to go home before shutting the door in his face. Toby goes back to his room and finds that Jude and Casey are gone, and as he packs his things in preparation for leaving the university, he finds a message on his answering machine from Jude saying that he left a “Christmas present” for him in his desk drawer and that he wants him to meet him and Casey outside Larry’s place at midnight. Toby discovers that the “present” is a handgun and realizes that Jude is planning to take the money by force. Once Jude and the unaware Casey arrive outside Larry’s place, he takes out his own gun and a ski mask and tells Casey to wait for him, having opted to get the money through committing robbery and having Casey serve as the getaway driver. Casey is initially dead set against this idea and spends some time arguing with Jude about it, but ultimately relents. Thankfully, Toby shows up and halts Jude as he is starting his approach, and he knocks Jude around a little and yells that he knows of a way that they can get the money without any violence or worse.

Toby meets Larry face-to-face the next day, and he proposes one last bet to the mobster: Larry can pick the team and the game, and if he wins, then he and his friends will pay him the $100,000 and quit being bookies, but if they win, then he must leave them alone and forget that any of their unpleasant experiences ever happened. Larry accepts the deal and selects a championship boxing match, with him betting on the challenger and leaving Toby and his pals to bet on the champion. However, the guys immediately figure out that the match will be fixed, so they take the opportunity to liquidate all of their assets and bet every cent they have against the champion through another bookie. Predictably, the challenger wins the fight, and the guys win what turns out to be $400,000. They pay Larry $100,000 as promised, then split the rest between each other and leave the bookmaking business for good. 

Toby narrates that Jude flunked out of college soon after, but remarks that he isn’t the first genius to do so, and though they stay in touch, things aren’t the same as they used to be. Casey switched majors, made the Dean’s List, and got himself some new friends, but he doesn’t see Casey too often anymore. As for him, he lost his scholarship due to letting his grades slip under the stipulated grade point average, but his winnings have him covered right into grad school. He also paid Hunter a visit and asked her for a second chance, and the movie ends with him playing a best-of-three foosball game against her for that chance, with him apparently winning.