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England, 1748. England is infested with highwaymen, such as Will Plunkett, a London based criminal working with a partner. However, very soon into the film his partner is killed by Thief Taker General Chance, and Plunkett finds himself on the run from the local constabulary.

This incident was witnessed by Captain James Macleane, who was being taken to a debtor's prison. He also sees Plunkett's partner swallow a ruby, which he sees as his ticket out of debt, and, after narrowly escaping discovery by Chance, he goes to the cemetery and tries to exhume the body and retrieve the ruby.

Unknown to him, Plunkett is also waiting there, and he forces Macleane to give the ruby to him. He then also swallows it, as they are both found by Chance's men. They go together to Newgate prison, and Plunkett realises that, because of Macleane's nobility, he can give the ruby to Macleane and he can use his influence to buy them both out of prison. This, despite protests from Macleane, starts a partnership which could be very successful, where they use Macleane's title to get to know the rich, and Plunkett's brains and planning to rob them later on. However, this all goes haywire when Macleane falls for the beautiful Lady Rebecca and lets their secret slip.

Eventually, Plunkett's plans to escape the country to America are spoilt by Macleane's uncontrollable spending, and Plunkett leaves him to the gallows. However, Plunkett comes back at the very last minute to save his friend, and all three leave for America. At the very end we see Plunkett get his own back on Chance, as he shoots him in the face in the sewer.

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