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Dreams and Nightmares, Deferred: The Unlikely and Extraordinary Freedom of Meek Mill

How the Philly rapper, currently out on bail, became a cause célèbre, a local sports icon, and a vessel for the powerful and influential

Getty Images/Ringer illustration

Earlier this month, Meek Mill shared a podium with Tom Wolf, the governor of Pennsylvania. The two men discussed the more brutal and maddening aspects of the state’s prison system, which—after 10 years of legal turmoil—recently released the Philadelphia rapper on bail. “I’ve been tangled in the system since 18 years old,” Meek said. “I spent time with these men and women, and watched families being broken apart because of drug addiction, mental illness, and technical violations.”

Meek’s near-decade of probation proved byzantine in the extreme. In 2008, a court convicted Meek on gun and drug charges. For more than a decade since his initial arrest, Meek has faced hearings and additional jail time as punishment for probation violations, many of which his busy music career seemed to render unavoidable. Last month, the Pennsylvania Supreme Court ordered Meek’s release on bail only after Wolf and the Philadelphia district attorney, Larry Krasner, raised doubts about the rapper’s arresting officer, who was being investigated in a corruption probe. Though he’s out bail and possibly facing a new trial, Meek’s release has come as a great, conclusive relief for the rapper and his fans. So far, he’s only partially integrated into the hip-hop ecosystem’s daily grind. (“I ain’t write one rap in jail,” Meek told Power 105.1 host Angie Martinez.) For now, he’s an activist—and an unlikely political mascot.

For rappers, the post-prison publicity blitz is a common ritual—sometimes defiant, sometimes muted, always grateful to be home. In the 1990s, Snoop Dogg, on trial for murder, and 2Pac, imprisoned for sexual abuse, both incorporated their high-profile legal peril into their music and mythology. In the present decade, fans have sustained years-long hashtag emancipation campaigns in support of their favorite rappers, most notably Pimp C, Boosie Badazz, Max B, Gucci Mane, and Meek. Often, these campaigns do more to fortify a rapper’s esteem than any one, hit single. When Gucci Mane went free in May 2016—four months earlier than expected—he immediately achieved heights of acclaim that mainstream publications, such as Vogue and Rolling Stone, had never afforded him during his musical peak in the late 2000s. Gucci’s music label, 1017 Records, compiled hundreds of old recordings and released dozens of mixtapes in the rapper’s absence, but those projects mostly abstracted his legacy; the rapper’s fans knew they were listening to scraps and hints of the old Gucci, all while the true Gucci languished for several years in an Indiana prison, far removed from any recording studio.

In contrast, Meek has recorded throughout his years-long legal ordeal. You can hear it in his performances. On songs, Meek and his labelmates, Rick Ross and Wale, would joke about the rapper’s indefinite probation. Among fans, Meek’s judge and probation officer both became familiar, foreboding characters, obscured by the rapper’s refusal to name names, but easy enough to discern from the increasingly bewildering news articles about Meek’s latest interactions with the court. Meek’s legal peril wasn’t just a setback—it was a riddle.

Only after the (retired) arresting officer Reginald V. Graham’s “credibility issues” came to light did the governor and the district attorney lobby for Meek’s release. For a month or so before his release on bail, Meek’s emancipation was—rather suddenly—a foregone conclusion.

Upon the rapper’s April 24 release, Michael Rubin, the co-owner of the Philadelphia 76ers, escorted Meek from jail straight to the Wells Fargo Center, where Meek greeted camera crews and palled around with Kevin Hart as the 76ers played Game 5 of the Eastern Conference first round against the Miami Heat. As with post-prison Gucci, the media and the rapper’s fans have celebrated post-prison Meek like never before. The rapper gave his first, big, post-release interview not to a music publication, but rather to Lester Holt, reporting for Dateline. Meek’s also stopped by The Breakfast Club and First Take to discuss prison reform and corrupt cops. This past weekend, Meek performed a surprise set at the annual Miami rap festival Rolling Loud, his freedom on spectacular display. Three weeks after his release on bail, Meek is taking the biggest victory lap of his career.

Occasionally, Meek’s ingratiation has underscored the awkward, uneven relationship between black stars and white power—an imbalance that has in the past couple of years played out most dramatically in the world of music and sports. Two weeks ago, Meek and Gucci both joined New England Patriots owner Robert Kraft courtside as the 76ers played against the Boston Celtics, and fans sneered: What could Kraft—a Trump confidant whom Meek claims as a friend—possibly want to do with two black, rebellious, formerly incarcerated rappers, one of whom has made it his cause to empower other inmates?

Ideally, the celebration of Meek Mill would underscore the brutal logic employed to justify, and define, his probation. But it seems far more likely that Meek’s newfound allies—including powerful figures such as Kraft and Wolf—will only obscure his concerns, much as the cheery atmosphere of the NBA playoffs obscured the awful complexity of Meek’s legal status. Generally, the media has rendered the story of his incarceration as a generic, and thus palatable story of one young man overcoming some nebulous odds. It is difficult to imagine any NFL owners rallying around Meek Mill, the civil rights activist—especially given the great lengths NFL owners went to stifle civil rights activism among black players within their own organizations. This is the paradox of Meek’s freedom: He’s released from physical captivity, and now he roams all throughout media and popular culture, but still, he remains on bail and best behavior, under more watchful eyes than ever, captive to the whims and personal loyalties of powerful men such as Kraft—figures who might align themselves with Meek’s significance and exploit his credibility while cheapening his cause.

The dynamic is broader and older than Meek Mill. For more than a quarter century now, young, black musicians have turned to hip-hop—a dominant, lucrative musical genre—as a clean professional recourse from an otherwise bleak outlook. The genre also serves as a seductive political channel, where white audiences might come to examine black experience, at a distance, and empathize with black people; in Meek’s case, criminal justice reform. Unfortunately, empathy doesn’t always work quite like this. At Rolling Loud, Meek performed his signature record—the tumultuous “Dreams and Nightmares”—and the crowd chanted along, even as Meek lost his breath and dropped the verse. Meek released Dreams and Nightmares, his major-label debut album, six years ago. Ever since the song’s release, fans have come to regard the Dreams and Nightmares intro as Meek’s crowning achievement. It was the song that scored the Philadelphia Eagles’ triumphant rush to a Super Bowl victory. After so many listens, it’s easy to remember the lyrics. And yet it’s easy to forget, or overlook, that the song’s plaintive first half is a rumination on jail time and opportunities lost to a gruesome and possessive system. “Seen my dreams unfold / Nightmares come true.” The song’s second half takes an exhilarating turn as Meek, seemingly invincible, raps wild and free. In real life, Meek’s freedom is far more tentative, still dependent on powerful whims and court dates, as always.