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In a Boston hotel room, Erwin Weaver finds himself being blinded with a bright spotlight and informed by a man, using a microphone to disguise his voice, that he can earn $50,000 for buying a Ford station wagon and driving it as instructed, whenever he is called. The mysterious man is millionaire businessman Thomas Crown, who later, bored with his various successes and disenchanted with the establishment of which he is a part, places phone calls to five men stationed at various phone booths around town. The men, who call him "Charlie," then agree to field calls again at precise intervals until each receives the signal from Tommy to "go." At the signal, the men head to the Mercantile Bank, where two of them commandeer an elevator, another quietly holds up the security guard, and another takes control of the elevator bank on the ground floor, holding bystanders at gunpoint and forcing to the ground two guards transporting over $2.5 million in cash. When one customer tries to run, he is shot in the leg, after which the robbers carry the bags of money out the front door, where Erwin waits in the station wagon. Dropping smoke bombs down the hallway, the robbers signal Erwin to drive off and then casually stride down the street. Erwin, nervous and inexperienced, is briefly caught in traffic jam, where he watches the police speed to the bank and round up the witnesses. Finally, he is able to drive away and, unaware that Tommy is following in his Rolls Royce, proceeds to the agreed-upon meeting point at a cemetery. As instructed, Erwin deposits the bags of money in a garbage can, changes the car's license plates and drives off. Posing as a mourner, Tommy retrieves the money and returns to his mansion, where he enjoys a celebratory drink in solitude. Meanwhile, Lt. Eddy Malone leads the police investigation, but finds few clues to the meticulously organized crime. After a witness identifies the station wagon, Eddy orders all similar cars searched, and although Erwin is stopped, the car passes inspection and he is released. Tommy flies to Geneva, where he deposits some of the cash in a secret bank account, easily convincing the bank manager to accept the new account without any personal information. Insurance investigator Jamie McDonald, furious that his company must pay off the bank, insists that Eddy work with a specialist, Vicki Anderson. Eddy is at first dismissive, but upon meeting the charming and sophisticated Vicki, allows her access to his files. She tells him that every crime has a personality, and despite disdaining her intuitive approach, he soon recognizes her intelligence. While they mull over how the crime has been accomplished, Tommy pilots his private plane and relaxes with his girl friend, Gwen. After a week of contemplation, Vicki deduces that the robber has transported the money to a bank in Switzerland over multiple airplane flights, knowing that the country's customs agents rarely inspect baggage. Realizing that a check of airline records would reveal repeat passengers, Eddy grows more enthusiastic about Vicki's unorthodox methods. She then wonders if the robber's cohorts could have been strangers, paid off in installments, and suggests that they place an advertisement offering a reward for anyone who has noticed a loved one who was out of town during the robbery and suddenly come into possession of a sudden influx of cash. Later, the two consider photographs of the short list of men who lately have made multiple trips to Switzerland. After instinctively discarding most of the suspects, Vicki sees Tommy's picture and is instantly attracted to the urbane entrepreneur. Attending his polo game soon after, she brazenly attracts his attention by filming him with a home movie camera, and later declares to an unconvinced Eddy that Tommy is definitely the culprit. Knowing he will be there, she attends an art auction, prompting Tommy to outbid her on a set of lithographs in order to have an excuse to approach her. As they talk, she reveals immediately that she is investigating him as a suspect in the bank robbery, causing him to laugh incredulously at her candor. Over dinner, the two well-matched adversaries spar verbally, their attraction growing. Later, while Tommy notes that his house is being watched, Eddy wonders to his assistant why a man as wealthy as Tommy would rob a bank, concluding it must be "for kicks." The newspaper ad attracts the attention of Erwin's irritable wife, who calls with information about Erwin's suspicious behavior. Although Eddy expressly forbids Vicki from pursuing Erwin using illegal means, she hires private detectives to steal Erwin's station wagon and kidnap his son, demanding $5,000 in ransom. Refusing to call the police, Erwin delivers the money only to find Vicki, who returns the boy and cash, which she points to as proof of his involvement in the robbery, and extracts a full confession. Eddy, jealous at how impressed Vicki is with Tommy's plot and appalled by her unethical techniques, questions her morality, causing her to admit with anger that she is indeed immoral and interested only in her compensation, ten percent of the recovered money. Vicki then invites Tommy to meet her at the police station, where she and Eddy watch through a two-way mirror as he waits in a room with Erwin. Erwin, however, has no idea what Tommy looks like, and Tommy reveals no glimmer of recognition. After Vicki introduces Eddy to Tommy and the two greet each other warily, Tommy brings her to his house, where she admires his refined taste. Over drinks, she taunts him that he will eventually lose their rivalry, then challenges him to a game of chess. During the intense game, their sexual chemistry reaches a peak, and finally he pulls her to him for a long kiss. As the pair continues to date, their romance deepens, as does their psychological struggle. Weary of being trailed by police and audited by the IRS, Tommy deliberately begins dating Gwen again, knowing Vicki will be informed. Upset, she confronts him about Gwen, but he replies that he is merely testing her devotion. They visit his unbuilt beach house, which consists only of a foundation and fireplace, and happily wander the cozy town. In a spa sauna, Vicki urges Tommy to let her cut a deal for him, but when he instructs her to call Eddy, as he has presupposed, Eddy refuses any deals. Confused by her feelings of guilt, Vicki is further shocked when Tommy declares that he is planning another robbery. One night soon after, he announces that the robbery will take place the following day and informs her of the cemetery at which he will pick up the money, stating that he is testing her to ensure that she is on his side. Despite her dismay and hesitance, Vicki informs Eddy about the pickup, and the next day they await Tommy at the cemetery. When it appears that he is not coming, Eddy angrily questions Vicki if she has been honest, but just then, the Rolls Royce drives in with a funeral procession, then veers off toward them. Eddy triumphantly has the car surrounded, but when Vicki opens the door, the driver, a messenger, hands her a telegram from Tommy. It states that he has "left early," asks her either to join him with the money or keep the car, and is signed "All my love, Tommy." As Tommy jets away to safety, wondering what Vicki will do, she tears up the telegram and searches the sky, overcome by emotion.