Plot

A debonair, adventuresome bank executive believes he has pulled off the perfect multi-million dollar heist, only to match wits with an insurance investigator who will do anything to get her man.

Four men pull off a daring daytime robbery at a bank, dump the money in a trash can and go their separate ways. Thomas Crown, a successful, wealthy businessman pulls up in his Rolls and collects it. Vickie Anderson, an independent insurance investigator is called in to recover the huge haul. She begins to examine the people who knew enough about the bank to have pulled the robbery and discovers Crown. She begins a tight watch on his every move and begins seeing him socially. How does the planner of the perfect crime react to pressure?—John Vogel <jlvogel@comcast.net>

An unknown man hires four unrelated men to carry off a bank heist of over $2 million. The four meet for the first time during the actual heist itself, which is carried off successfully. Their unknown leader is suave and wealthy Sir Thomas Crown, an executive at the bank that was hit. Eddy Malone, the Boston police detective in charge of the case, is coming up empty in his investigation, that is until beautiful insurance investigator Vicki Anderson comes on the scene. Anderson, admittedly self-serving in that she works on commission, thinks like a thief and works on her instincts. Looking through the evidence, she believes that Crown is her man. Upon meeting, Anderson knows that Crown is the thief. Crown knows what Anderson believes as she tells him as much. Despite their positions, they are immediately attracted to each other and begin a relationship. But this does not stop their cat and mouse chase. However, the role of the cat and the role of the mouse are not always clear cut.—Huggo

Millionaire businessman-sportsman Thomas Crown (Steve McQueen) accomplishes a perfect crime by orchestrating four men to steal $2,660,527.62 from a Boston bank ($22,389,167 in 2022 dollars), along with a fifth man Erwin who drives the getaway car with the money and dumps it in a cemetery trash can. None of the men ever meet Crown face to face, nor do they know or meet each other before the robbery. For planning, men were summoned to a hotel room, where they faced a set of bright lights, and a man speaking into a microphone. They are promised a payment on $50,000 in monthly installments, so they don't spend it all quickly. Thomas asks Erwin to buy a used car, with cash money provided by Thomas.

The 4 men are Carl (Yaphet Kotto), Dave (Sam Melville), Benjy (Todd Martin) and Abe (Adison Powell). Thomas coordinates the actions of the 4 men via public telephones. Abe and Carl get into a bank and take control of an elevator. Dave takes control of the security room. They take possession of a money trolley, when it is being moved by the elevator to the vault. Once the money is in their possession, they move it to Erwin's car waiting outside. Erwin dumps the money in a garage can in a cemetery and then changes his number plates.

Crown retrieves the money from the trash can after secretly following the driver of the getaway car. He deposits the money into an anonymous Swiss bank account in Geneva, making several trips, never depositing the money all at once so as not to draw undue attention to his actions.

The police are not able to find anything. All suspects were wearing sunglasses and hats. They cannot find the getaway car.

Independent insurance investigator Vicki Anderson (Faye Dunaway) is contracted to investigate the heist; she will receive 10% of the stolen money if she recovers it. Vicki believes that the money has been moved to numbered accounts in Switzerland. The money would have to be moved by plane, and in multiple trips. She asks the Boston police to make a list of people who made multiple trips to Switzerland recently. Vicki believes that the robbery was masterminded by an unknown entity, who orchestrated the robbers, who probably never even met each other before the day of the heist. Vicki runs an advertisement in the papers for news on the heist, against a reward of $25,000.

When Thomas first comes to her attention as a possible suspect, she intuitively recognizes him as the mastermind behind the robbery, and shortly thereafter guesses that he organized the robbers so none of the men knew him or met each other.

Thomas does not need the money, and in fact masterminded the robbery as a game. Vicki makes it clear to him that she knows that he is the thief and that she intends to prove it. They start a game of cat and mouse, with the attraction between them evident. Vicki declares to Thomas that she is after him. Thomas already has $4 Million as net worth, and there is no motive for him to steal any more. Their relationship soon evolves into an affair, complicated by Vicki's vow to find the money and help detective Eddy Malone (Paul Burke) bring the guilty party to justice.

The reward offer entices the wife of the bank robbery's getaway driver, Erwin Weaver (Jack Weston) to "fink" on him for $25,000 ($210,383 in 2022 dollars). There are 2 witnesses who saw Erwin drive away from the bank and Erwin paid for the Ford station wagon in cash. Erwin gets monthly payments into his bank account, from a numbered account in Geneva. Vicki finds out that he was hired by a man he never saw, but whose voice he heard (via a microphone). She tries putting Erwin in the same room as Thomas, but there is no hint of recognition on either one's part. Thomas knows that by now his home has been bugged by the police. He invites Vicki for a game of chess. They end up having sex. Vicki asks Eddy to keep the pressure on Thomas. Vicki believes that Thomas is bound to make a mistake. While Vicki continues to spend personal time with Thomas. News of their romance reaches Eddy. Eddy cannot make up his mind about what Vicki is up to. Eddy tells Vicki that Thomas has been cheating on her. He says that after leaving Vicki, Thomas goes to meet another girl.

However, while Vicki is clearly closing in on Thomas, using the Internal Revenue Service (IRS) as leverage against his liquid assets, he forces her to realize that she is also becoming hemmed-in by her emotions. When she (seemingly) persuades him to negotiate an end, his point is proven when Eddy stubbornly refuses to make any deal.

Thomas organizes another robbery exactly like the first with different accomplices and tells Vicki where the "drop" will be, because he has to know for sure that she is on his side. The robbery is successful, but there are gunshots, and the viewer is left with the impression that people might have been killed, raising the stakes for Vicki's decision.

Vicki and the police stake out the cemetery, where they watch one of the robbers make the drop and they wait for Thomas to arrive so they can arrest him. However, when his Rolls-Royce arrives, she sees that Thomas has sent a messenger in his place, with a telegram asking her to bring the money and join him - or if not, "you keep the car". She tears the telegram to bits and throws the pieces to the wind, looking up at the sky with tears in her eyes. Crown flies away in a jet.