How Meek Mill’s Legal Woes Turned Him Into an Activist for Criminal Justice Reform

Meek Mill never set out to be an activist for criminal justice reform. Nursing a glass of green juice at a Beverly Hills hotel shortly after performing at Staples Center, the 32-year-old sometimes seems like he’d prefer to discuss just about anything else. His rap career, for one, which after nearly a decade of legal stops and starts, finally reached the level it had long promised with last winter’s platinum-certified “Championships.”

But activism — or as he prefers to call it, advocacy — is nonetheless something that’s been thrust upon him, and Amazon’s upcoming five-part docu-series “Free Meek” (it premieres Aug. 9) details how this quick, intense, yet often slyly irreverent rapper from North Philadelphia became the unlikely public face of America’s broken probation system.

“I don’t want to be a rapper who’s just this serious guy all the time,” he says. “I think most activists have it in their heart that this is what they love to do seven days a week. Me, I don’t love to do interviews about reform seven days a week. This wasn’t a part of my life until it became my life experience, but I’ve seen people stand up for me, so I’m gonna use what I’ve built up through my rap career to pay people back and get my message across.”

Perhaps it’s his natural reticence that makes him such an effective spokesman. Up until July 24, when a Philadelphia appeals court finally overturned his 2008 conviction on drug and gun charges and granted him a new trial, Meek had spent his entire adult life in the criminal justice system.

It all started when he was arrested for gun possession as a teenager. He admitted he had a gun from the start, but was stunned to find a 19-count indictment against him, with charges for everything from drug possession to felony endangerment, all of which he has consistently denied. Most shocking to him was an officer’s claim that he had pointed a gun at the arresting officers. (As Meek notes wryly: “I don’t know the data on it, but just speaking from my experience of being a person who’s not crazy, I know pointing a gun at a police officer for a young black kid at night time is suicide.”)

He thought he caught a lucky break when a judge offered him a plea deal (a year in prison, followed by five years of probation), but he quickly found that even out of prison, the system could be just as stifling.

For the next decade, Meek watched as his burgeoning rap career was sabotaged by the conditions of his constantly ballooning parole, which frequently kept him from touring and promoting his music and often saw him back in trouble for minor infractions. This culminated in 2017, when Meek was given a two-to four-year prison sentence for parole violations after being caught in an Instagram video popping a wheelie on a dirt bike.

“I couldn’t see my future in the music business anymore,” he says of the sentence. “If you miss out for two years, your whole career could possibly be over. You can’t really see the future; you can’t see the hope. And your dreams aren’t really the same when you’re locked in a prison.”

The almost farcical discrepancy between the harmlessness of Meek’s violations and the severity of the punishment turned him into a national cause célèbre: Protest marches were held; powerful friends like Jay-Z (whose Roc Nation manages Meek’s career and his Dream Chasers label), Robert Kraft and Philadelphia 76ers partner Michael Rubin demanded his release; and in a show of support, the Philadelphia Eagles stormed the field for the 2018 Super Bowl to Meek’s signature track, “Dreams and Nightmares.”

Despite all that assorted firepower, Meek spent five months in prison before being released on bail, including time in solitary confinement, which he calls “the worst experience of my life. I’ve been around drugs, been around murder, death, funerals, all these things, but being locked alone in a cell 24 hours, seven days, was the worst mental fight I’ve ever been through.”

While Meek was still inside, however, the seeds of “Free Meek” were germinating. Rubin encouraged producer Eli Holzman to develop a documentary on his struggles. Holzman partnered with Roc Nation and journalist Paul Solotaroff, with Amazon soon coming on board.

“Meek was still in jail at that time, and the earliest interviews with him were over the phone from prison,” says Chris Castallo, Amazon’s head of unscripted. “We had no idea if and when Meek would get out, or where the story would lead.”

Meek is well aware that he’s an unusual case — most people in prison for parole violations don’t have billionaires advocating for them on the outside — but by focusing on the particulars of his case, the series illustrates just how easily well-meaning parolees can get sucked back into the revolving door of the system. Meek says he hopes projects like “Free Meek” and Ava DuVernay’s “When They See Us” will open eyes and raise awareness, all while his recently established nonprofit, the Reform Alliance, is petitioning for more specific changes to the probation system.

Meanwhile, he’s making up for lost time in the studio, “taking my trauma and making it rhyme.”

Perhaps the most fascinating element of his last album, “Championships,” was how boldly it managed to encompass his own struggles and newfound role as a political advocate, without letting those struggles define him as an artist. There’s plenty on the album that addresses Meek’s causes, with tracks like “Trauma” and “What’s Free” offering vivid, nuanced accounts of both the justice system and the larger conditions that cause so many to fall into it. But there’s also a gleefully obscene Cardi B feature, a radio hit with Drake, and plenty of wild, perfectly-timed insults that recall his teenage days as a battle rapper. For Meek, there’s no reason that his visibility as an advocate should lead him to compromise or blunt his rougher edges in the studio.

“Rapping, no matter what it’s about, it’s art,” he explains. “You go an art museum and you might see butt-naked people in a painting, then you go to another room and it’s a picture of a tree. They’re both art, right? That’s what I do. I try to always deliver enough [substance] to get my message across, but to still have fun, and have no boundaries on my music. Just because I represent reform, I didn’t want to make it look like that I couldn’t talk about what I wanted to, rap about what I wanted to rap about, and be the artist that I used to be.

“Because in my life I’ve been probably making good money for myself from the age of 23 on up, but before that my life was full of trauma, full of seeing violence, full of failure. So that was basically my lifestyle. And being in the streets is almost like a religion, so that’s still installed in the back of my brain somewhere, and when I make music I still talk about it. But the idea now is to try to balance it out.”

In a bitterly ironic way, it was only after so many setbacks, heartbreaks, and missed opportunities thanks to his long nightmare in the justice system that Meek developed into such a fully dimensional artist.

“Do I think about what it cost me? Sure,” he says of his protracted legal battle. “But at the same time, it all comes together. I overcame it, and it gave me a great story, and hopefully it inspires people later on. It kind of made me into who I am now.” 

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