The rapper has publically declared his anger at the America's criminal justice system on numerous occasions and has called Meek's 2-4 prison sentence "unjust". But others connected it back to 2014, where he first wore the T-shirt in support of the Wins & Losses artist as he struggled through another legal fumble that led to his incarceration. On Friday, Jay-Z wrote an op-ed for The New York Times in support of his Roc Nation colleague.
The OVO boss has famously worn the "Free Meek Mill" shirt himself, on multiple occasions.
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Drake may seem like an unlikely Meek supporter, but the two have history together.
While hitting the stage during his Melbourne, Australia, stop for the Boy Meets World Tour, Drizzy took a moment to mingle with fans in the massive crowd.
Colin Kaepernick recently spoke to Meek Mill in jail and says that in spite of the circumstances, the rapper is in good spirits. Meek tried to discredit everything Drake did all his life, and even named the rapper's alleged ghost writer, Quentin Miller.