I need help analyzing what "rolled" means, What does it mean? "His ring, which he had rolled a drunk senior to get, was back on his finger."

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To roll someone is to mug him or her. This can mean beating the person up, or, if the person is drunk, as in this case, just robbing him. Usually, though, if you roll someone, you'd bop him on the head and roll him into an alley, where he'd recover a while later with a sore head and an empty wallet.

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