And now Meek Mill has been sent back to prison for up to four years after a judge ruled on Monday two new arrests meant he had once again failed to live up to the conditions of his release.
Mill and his counsel plan to appeal.
The 30-year-old rapper, who was already under probation for a drug and weapons case, was arrested twice this year. She said Mill's sentence would be served in state prison, where he would be eligible for state parole supervision after two years.
Meek's legal issues continued in March, when he was arrested for fighting in the Philadelphia airport (The charges were dropped when he agreed to perform community service).
However, Mill's plea did not make the judge change her decision and she ordered him to be taken into custody.
The sentence came as a surprise even as prosecutors recommended that he should not be punished as he has been off drugs since January and complied with most terms of his probation. He was released in 2009 with a five-year probation agreement.
Rap mogul Jay-Z wrote on Facebook that the sentence was "unjust and heavy-handed". But the judge insisted, saying that she had been trying to help him for about a decade and he refused, insisting on doing whatever he wanted.
Meek is, of course, a member of Jay-Z's Roc Nation, but clearly with those strong words their bond is bigger than just a business relationship.
Raised by his mother in Philadelphia after his father was killed, the rapper born as Robert Williams was put on probation after a 2005 arrest on drug and gun possession charges.
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