CIA operative Nathan Muir (Redford) is on the brink of retirement when he finds out that his protege Tom Bishop (Pitt) has been arrested in China for espionage. No stranger to the machinations of the CIA's top echelon, Muir hones all his skills and irreverent manner in order to find a way to free Bishop. As he embarks on his mission to free Bishop, Muir recalls how he recruited and trained the young rookie, at that time a sergeant in Vietnam, their turbulent times together as operatives and the woman who threatened their friendship.
Brian Kessler, a journalist researching serial killers, and his photographer girlfriend Carrie set out on a cross-country tour of the sites of the killings. Sharing the ride and their expenses are Early Grayce, a paroled white trash criminal, and his girlfriend Adele. As the trip progresses, Early begins to appear more and more unstable, and Brian and Carrie begin to fear that they may have a real-life serial killer in the back seat of their car.
The plot centres on a huge diamond stolen from the Orthodox Jewish diamond district in Antwerp by a gang of armed robberies. The diamond's thief and courier, Franky Four Fingers (Benicio Del Toro) must deliver the valuable gem to his crime boss, "Cousin Avi" (Dennis Farina) in America. First he travels to England to give smaller stones to Avi's cousin, Doug "The Head" (Mike Reid) and other local Hatton Garden jewelers. But instead, hapless Franky is drawn into the whirlpool of rather undesirable events. In London he can't help placing a bet on an illegal boxing bout by Boris "The Blade" (Rade Serbedzija) who proves to have taken him over - local pawnshop owners Vincent (Robbie Gee) and Sol (Lennie James), along with their getaway driver, Tyrone (Ade) waylay and rob him at the bookies. As expected, the diamond goes missing. When bad news reaches Avi's ears, he blows off and rushes with a legendary hit man, 'Bullet Tooth' Tony (Vinnie Jones), to London to find Franky and the missing stone. Moreover, the priceless gem is hunted by cunning Mickey O'Neil (Brad Pitt), morose Brick Top (Alan Ford) and many other miscreants, each of whom strives to hit the jackpot.