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Jack Sheppard, an apprentice locksmith in London in the 18th century, becomes a jewel thief in order to save his brother Tom from the gallows. To accomplish his robberies, he must join forces with underworld figure Jonathan Wild, a notorious "thief-taker" who turns in robbers for rewards and who captured Tom. As part of the agreement, Jack joins two of Wild's men, Blueskin and Leatherchest, in stealing a precious jeweled tiara from a count, but he is doublecrossed when Wild ships Tom off to America as a prisoner. Since the deportation will leave his brother's wife and children penniless, Jack swears to get even with Wild but is deceived by the master criminal when Wild plants the tiara in Jack's room. "Edgworth Bess" Lyon, a pretty barmaid who loves Jack, finds the tiara and thinks it is a present for her. Wild's men rush into the room, spot the tiara, and arrest Jack for theft; but he soon escapes from prison and begins a well-publicized career as a highwayman. Meanwhile, Wild's men kidnap Bess and use her as bait to recapture Jack, who is once again sent to prison and locked in an escape-proof cell. When Lady Darlington, formerly a willing victim of Jack's escapades, sends him an invitation to dinner, Jack miraculously breaks out of jail again, to the delight of London citizens who have by now elevated him to legendary status. Interest is so strong, in fact, that King George I bets the Lord Chancellor 1,000 guineas that Jack can steal the Chancellor's chain of office. The robbery is a success, and Jack plans to trade the chain of office for his freedom. Instead, he uses it to free Blueskin and Leatherchest when he learns that they are about to be hanged by Wild. Against the protests of the Lord Chancellor, Jack is given the death sentence by his old nemesis, but the execution draws so many people that Jack is able to make his escape and return to Bess once again.