Career criminal Forrest Tucker, a man on the run for two years following his daring escape from San Quentin State Prison in 1979, finds himself tangled in another bank heist. At the age of 74, this charming rogue cleverly evades the police by pretending to assist a woman, only moments later to find himself driving off unnoticed as the authorities pass by. This woman, Jewel, expresses her gratitude by buying Forrest lunch at a diner, where their conversation unfolds. Despite introducing himself with a false name, Forrest feels a strange attraction towards Jewel, to the extent of jokingly confessing to her that he is a bank robber—though he quickly brushes it off as a mere jest. Their bond grows as they spend time together at Jewel’s farm, where Forrest admires not just her spirit, but the peaceful life she leads. Enchanted by her, he devises a plan to surprise Jewel by paying off the remaining balance of her mortgage. However, his excitement turns to frustration when he discovers that such a gift would require her signature, thereby ruining the surprise.
As Forrest continues his criminal exploits, he manages to pull off a series of heists with remarkable finesse, often avoiding the need to draw his gun at all. Meanwhile, Detective John Hunt compiles sketches of Forrest based on witness accounts that paint him as not just a criminal, but a "charming and gentlemanly" figure. John takes these sketches to the evening news, appealing for anyone with information to come forward. Soon, the case garners enough attention for the FBI to step in.
An intriguing twist occurs when a woman named Dorothy claims to be Forrest's daughter. Although John is no longer working the case, he meets with Dorothy, who reveals that she was born while Forrest was imprisoned, leaving him oblivious to her existence and the fact that he is now a grandfather. Further investigation leads John to consult Forrest’s former lawyer, who expresses disbelief at the idea of Forrest ever firing his weapon during any standoff, insisting that what sounded like gunfire was merely the backfiring of Forrest’s car.
One evening, during a dinner date with Jewel, Forrest inadvertently spots John dining with his wife Maureen. In a moment of camaraderie, Forrest tries to uplift John's spirits but is unsettled when John unexpectedly calls him by his real name, signaling that they both are aware of the game being played.
As night falls, police lie in wait for Forrest outside his home. In a tense moment, he flees, but his car backfires, prompting the police to shoot at him, hitting him in the arm. He makes a narrow escape and rushes to Jewel’s farm. Upon arrival in the early hours, rather than waking Jewel, he takes one of her horses for a leisurely ride, a long-held dream he had yet to fulfill. Unfortunately, his peaceful moment is short-lived as police vehicles storm into Jewel’s property, leading Forrest to reluctantly surrender. During his visit, Jewel learns of Forrest's storied history of escapes from various locations, revealing a list of his sixteen prior attempts, with a space for a possible seventeenth—a blank page symbolizing hope.
Upon his release from prison, Jewel is there waiting for Forrest, welcoming him to her farm and offering him a place to stay as long as he desires. Their life together is serene, but the restless spirit within Forrest stirs. One day, under the guise of running an errand, he calls John from a payphone. When John asks if he is okay, Forrest cryptically replies that he is "about to be" before stepping into a nearby bank. Title cards present a shocking revelation: "Forrest Tucker robbed four more banks that day. When he was finally caught, the officers on the scene noted that as they arrested him... he was smiling."
