“I was in the back seat of a car and a shooting happened, and so all of us ended up going to jail for it,” said Charlamagne, adding that no one was killed. Two other times, he said, he was arrested on charges of possession of marijuana and cocaine with intent to distribute. (Though Charlamagne says he is 33, arrest records put his age at 35. “In the hip-hop culture, kids see age and automatically dismiss you,” he said, in responding to the discrepancy, not quite confirming which number was accurate.)

“The third time he got locked up, I let him sit there for approximately 41 days,” Mr. McKelvey said. “That’s when he called my wife and asked her to please get him out of jail. That’s when I decided ‘Enough is enough. I’ll give him another chance.’ ”

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