Gerry, a struggling gambler and real estate agent, meets Curtis, an itinerant younger gambler, at a casino in Dubuque, Iowa. Curtis buys Gerry a drink; at a bar hours later, Gerry sees Curtis and returns the favor, leading to a night of heavy drinking.Mississippi Grind 2015.
After an unsuccessful real estate showing, Gerry goes to a dog track with Curtis. They win a large bet, which Gerry gambles away. At a bar, they drunkenly attempt to bet $1,000 on a game of pool and are kicked out. Curtis explains to Gerry that “Machu Picchu time” is approaching – a phrase he uses whenever he leaves town. In the parking lot, Gerry is stabbed in an attempted mugging.
Gerry’s loan shark, Sam, threatens him to pay the money he owes her. Running into Curtis, Gerry proposes a gambling trip down the Mississippi River culminating in a New Orleans poker game with a $25,000 buy-in. Curtis agrees, spotting Gerry $2,000. Before hitting the road, Gerry steals the petty cash from his office.
They arrive in St. Louis, where Curtis reunites with Simone, a prostitute. After Gerry’s successful poker session on a riverboat casino, he and Curtis spend the night with Simone and fellow prostitute Vanessa. While Gerry bonds with Vanessa, Simone reminds Curtis she has been taken advantage of by a gambler before, and remains unwilling to run away with him. In Memphis, Gerry plays well at Texas Hold ’em but loses everything on the final “river” card. He lies to Curtis that he won $7,000, and asks to go to Little Rock to see his ex-wife Dorothy and estranged daughter. Gerry finds his daughter is at school; Dorothy catches him trying to steal money, and asks him to leave.
Curtis and Gerry visit a casino in Tunica, Mississippi, where Curtis’ VIP card is rejected; asking Gerry for money, Curtis discovers his lie. Disappointed in him, Curtis provokes strangers in the bathroom into assaulting Gerry, who later admits to his problems with money, and his belief that Curtis is his good luck charm.