Meek Mill was arrested for illegally possessing a firearm and assaulting the police when he was 18 years old. Since then, he has been arrested four times for parole violation. The now 30-year-old Wins & Losses rapper was convicted of drug dealing and gun possession in 2008 when he was initially sentenced to 11 to 23 months in prison. He secured an early release in 2009 with a five-year parole agreement, but sticking to the parameters of that agreement has seemingly given him trouble ever since.
In 2012, Meek violated his probation and had his travel permit revoked. He continued to violate the terms of his probation, mainly by not updating his travel plans, through 2014, when he was finally sentenced to six months in jail. He was released in December of that year, but violated again just one year later, resulting in 90 days of house arrest in February of 2016 and six more years of probation.
Unfortunately, he was unable to keep his cool on his last chance during an altercation in May of this year; during a confrontation with an employee at St. Louis International Airport, he was arrested for assault, which probably made for his last strike, but he was also arrested in August for racing dirt bikes in New York City, which probably didn’t help his argument much.