Immortalized in Sir Walter Scott's novel "Rob Roy", and in some passages in the poems of William Wordsworth, MacGregor was a Scottish highwayman and freebooter of uncertain loyalties. He was allegedly also a cattle thief and blackmailer, which at the time were still honorable highland practices. During the Jacobite uprising of 1715 he was purported to have plundered both sides impartially.

In 1722 Rob Roy was finally arrested and confined in Newgate Prison, London. He was pardoned in 1727, shortly before his scheduled deportation to Barbados.

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