The film commences with a captivating voice-over by producer Martin Scorsese, explaining the tactics employed by bettors at racetracks who deliberately place substantial wagers on specific horses to manipulate the odds and maximize their profits. We are introduced to Lily Dillon, portrayed by Anjelica Huston, a seasoned con artist in her 40s, who is firmly in the grasp of Baltimore gangster, Bobo Justus. Lily's primary task involves making these high-stakes bets on horse races. After accumulating significant earnings, she cleverly opens a concealed compartment in her car’s trunk, where she pilfers several thousand dollars from the payoffs—secretly blending this with the other funds she has illicitly taken from Bobo.
Lily receives a call from one of Bobo's associates while in New Mexico, instructing her to head to the downs in La Jolla. She agrees but plans to make a detour to Los Angeles to visit her estranged son. In L.A., we meet Roy Dillon, played by John Cusack, a 25-year-old who engages in various minor cons. One of his tricks involves displaying a $20 bill to a bartender, only to slyly switch it for a $10, thereby misleading the bartender into providing him change. However, one day, Roy’s deception backfires when a victim catches him, delivering a hard blow to his chest with a club. Suffering and in pain, Roy manages to return home, where he dreams of his initial encounter with Mintz, played by Eddie Jones, who serves as his mentor in the art of conning. Mintz had firmly advised him against partnering in cons, foretelling that it always leads to ruin.
Later that evening, Roy's girlfriend, Myra Langtry, portrayed by Annette Bening, who is also a grifter, visits him, and they share an intimate moment. The next day, Lily arrives, kicking off a tense reunion filled with unresolved emotions. Roy expresses his anger towards Lily for her absence over the past eight years, prompting an emotional exchange. Concerned about her son’s deteriorating health, Lily swiftly arranges for him to be hospitalized where he is treated for internal bleeding caused by the club's assault. When a doctor expresses concerns about Roy's condition, Lily’s desperation leads her to threaten him.
Both Lily and Myra pay Roy a visit at the hospital, and the tension between them escalates instantly. Lily regards Myra as a negative influence while Myra assumes Lily's presence could imply an inappropriate relationship with her son. In a twist, Lily decides to hire a nurse to initially care for Roy after his discharge, a gesture that Roy fiercely rebuffs.
Meanwhile, Myra struggles with her landlord who demands immediate rent payment. She insists on her reliability but ultimately offers to barter in an unexpected manner. Back on the road to La Jolla, Lily finds herself stuck in a traffic jam, causing her to miss a crucial bet for Bobo. When confronted by Bobo at his hotel, she faces his wrath over the missed opportunity, only to end up in a terrifying encounter that leaves her shaken but determined to maintain her composure.
Roy tries to make up for lost time with Myra, taking her on a romantic getaway where he cheekily cheats at a dice game, prompting Myra to reveal her own backstory involving con artist Cole Langley (J.T. Walsh). She narrates how they ran elaborate schemes targeting wealthy individuals, depicting a life filled with deception and danger. However, as Myra trails Lily to the horse track and discovers her shortcut in profits, she begins to plot against Roy, revealing her darker intentions.
After a harrowing series of events, a sudden twist of fate ensues. Lily receives dire news about Roy’s health, leading her to flee from the situation. Myra takes ruthless measures to tighten the noose around Roy, eventually instigating dire consequences for both women. The film reaches its tragic climax when Roy discovers the extent of deceit permeating his life, culminating in a heartbreaking confrontation between mother and son.
In a desperate bid for survival, Lily attempts to manipulate Roy into assisting her escape while revealing her deeply buried motivations. However, in a moment driven by anger and betrayal, Roy rejects her, leading to a calamity that forever alters their lives. Amidst chaos, Lily escapes, hauntingly leaving her son behind as he succumbs to his injuries, encapsulating the chilling essence of betrayal atop layers of emotional struggles and cunning deception.
