Is Meek Mill’s Friendship With Trump Supporter Robert Kraft an Unholy Alliance?

Meek has become the face of prison reform advocacy. But is his stance contradicted by his bromance with the billionaire Patriots owner?
Robert Kraft Meek Mill
Robert Kraft and Meek Mill, May 2018 (Jim Davis/The Boston Globe via Getty Images)

An odd scene: 77-year-old billionaire New England Patriots owner Robert Kraft prances around a stage in a Commes Des Garçons hoodie while Cardi B fittingly performs “Money.” His buddy, 31-year-old Philadelphia rapper Meek Mill, looks on, smiling in delight. Is this some alternate reality? No, it's just Super Bowl weekend, where strange things tend to happen.

2019 marked the second consecutive year in which the eventual champion has chosen a Meek Mill song as its theme. Last year, the Philadelphia Eagles adopted his now ubiquitous rags-to-riches classic, “Dreams & Nightmares (Intro),” as their anthem in pursuit of their first Super Bowl victory of the NFL’s modern era. This year, the New England Patriots, the Eagles’ opponent in Super Bowl LII, proceeded to tweet a highlight reel ahead of Super Bowl LIII set to Meek’s “Wins & Losses.” “You have to eat the dream...you have to sleep the dream...you have to see it when nobody else sees it. #EverythingWeGot featuring Meek Mill,” the message reads.

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It seems odd, if not disingenuous, for a franchise that has won six Super Bowls in the past 17 years—including three of the last five—to compare itself to an underdog, let alone one who’s faced odds far more grave than winning or losing a game. But this wasn’t the first instance of the Patriots laying claim to their unexpected ally. Last April, following Meek’s release from prison, the team tweeted a picture of him and Kraft with the following message: “Justice for our friend. Finally free.”

In November 2017, Meek Mill was sentenced to two to four years in prison for two nebulous “technical” probation violations despite his probation officer not recommending jail time for either incident. He has spent over a decade on probation after being convicted on gun and drug charges in 2008, but his recent incarceration gave criminal justice reform a famous face. #FreeMeekMill became a rallying cry and cause célèbre, drawing the attention of high-profile figures like Kraft, who he met through a mutual friend, Philadelphia 76ers co-owner Michael Rubin. Meek was released on bail (a spectacle that saw him transported from state prison to a 76ers playoff game via Rubin’s helicopter) after Pennsylvania Governor Tom Wolf and Philadelphia District Attorney Larry Krasner questioned the credibility of his arresting officer. He’s since vowed to help overhaul the system that’s hamstrung him, talking about his incarceration everywhere from The Breakfast Club to The New York Times, “Ellen,” and “Dateline.”

Last month, Meek launched a $50 million criminal justice reform organization called REFORM Alliance along with JAY-Z, activist and CNN commentator Van Jones, Rubin, and Kraft, among others. Once again, Robert Kraft’s proximity to not only Meek, but this initiative, raised questions. Kraft is a prominent friend and supporter of President Donald Trump, who campaigned on the type of “tough on crime” platform that has been correlated with the rise of mass incarceration in the U.S.

While REFORM Alliance’s objective is commendable and absolutely necessary, there’s cause for skepticism given the unavoidable questions surrounding its optics. The organization’s mission, according to its website, is to “dramatically reduce the number of people who are unjustly under the control of the criminal justice system—starting with probation and parole.” It’s reasonable to wonder how, exactly, the organization proposes to fulfill its mission.

In a statement to Pitchfork, Jones called the probation and parole systems “the twin hinges on a revolving door pulling people back into prison, again and again.” He said REFORM Alliance will aim to reduce the number of people under the systems’ control by supporting reform bills for both, beginning at the state level.

“Usually a probation violation is not a crime or a misdemeanor, but something as small as being late to a meeting because of traffic or the need to attend a job interview,” he says. “Yet, these small probation oversight violations trigger another 2-5 years of probation—or even jail time. We will support bills that apply common sense solutions to allow Americans with convictions to truly focus on rehabilitation and re-entry into society. We believe this approach could cut the parole and probation population in half and will still keep communities equally safe.”

Asked what specific policy changes REFORM Alliance is lobbying for, Jones said it will collaborate with policymakers and administrators to fight for reasonable limits on probation, beginning in Pennsylvania and New York:

“Pennsylvania has some of the country’s worst criminal justice laws and is one of only 15 states in the country that has no caps on probation. Meek Mill has been on probation for his entire adult life. If he happened to live in New York, he would have been out of probation in 5 years and spared from his recent nightmare. Pennsylvania Governor Tom Wolf has worked hard to make criminal justice reform a top priority, and we look forward to working with him to ensure that Pennsylvania leads the nation in rehabilitation and not incarceration. Positive steps like Pennsylvania’s Clean Slate Legislation give people the ability to have their records sealed from public view after 10 years of crime-free living if the original conviction was a low-level non-violent crime. It gives people a real chance at a fresh start. We are committed to rapidly enacting similar solutions across the country at the state level.”

That sounds great, but the looming question REFORM Alliance must answer is whether Kraft’s involvement undermines its stated purpose. On the harrowing “What’s Free,” from Meek’s most recent album, Championships, he lists Kraft among his most powerful supporters: “Maybe it’s the Michael Rubins or the Robert Krafts/Or the billionaire from Marcy and the way they got my back.” “It’s just sad. This guy’s great. Shouldn’t be here,” Kraft told reporters of Meek after visiting him in prison last year. “Makes it clear to me that we have to do something with criminal justice reform.”

Kraft’s concern with Meek’s legal problems and the unjust circumstances that created them are admirable, but the contradiction lies in his friendship with and continued support of a president whose administration has enabled private prisons to flourish. (The private prison companies GEO Group and CoreCivic were among the donors to Trump’s inauguration, as was Robert Kraft.) A president who has “jokingly” encouraged police brutality. A president who has empowered Immigration and Customs Enforcement (ICE) to run rampant, separating families while ordering a record number of immigrants to be detained and deported in 2018. (REFORM offered support for 21 Savage, who was recently detained by U.S. Immigration and Customs Enforcement.) A president who has authorized the U.S. Border Patrol to imprison over 15,000 migrant children, as of December 2018. And a president who admonished NFL players for joining Colin Kaepernick’s protest of the very thing, per Kaepernick himself, that has turned Meek’s adulthood into a minefield traipse: systemic racism.

Although a 2017 New York Times report revealed that Kraft called Trump’s comments about Kaepernick’s protests “divisive and horrible” and said they aren’t “in the best interests of America,” he, along with the rest of the league’s owners, voted to fine players for protesting police brutality and systemic racism last year at Trump’s behest. Two days before this year’s Super Bowl, Kraft told “Fox & Friends” he believed Trump was “working very hard to serve the best interests of the country.” You can’t play for both teams in this situation.

According to REFORM Alliance, Kraft was unavailable for comment due to “post-Super Bowl commitments.” Requests for comment made through both the New England Patriots and his holdings company, The Kraft Group, LLC, were not immediately answered. REFORM Alliance also stated that Meek Mill was unavailable for comment due to preparation for his upcoming tour. Jones, however, cited bipartisanship to reconcile Kraft’s support of Trump and the political differences within the organization. One such instance of bipartisan collaboration to address mass incarceration—if only at the federal level—was the First Step Act, a bill that makes provisions for sentencing reform and allows some individuals to qualify for early release.

“Both political parties passed the laws that led to mass incarceration; it will take both parties to reverse those laws. Therefore, a diverse set of allies must be willing to work together across political divisions to accomplish what needs to be done for our country,” he said in a statement. “Though I disagree with Trump on many issues, we were able to work together to pass the First Step Act. I’ve beaten up the White House because I’m a staunch proponent of immigrants’ rights, the environment and any number of other causes that might not align with the views of the President. We can be on opposite sides of 99 out of 100 issues, but we cannot get to a point where we’re so anti-Trump that we are ‘anti’ our own agenda. I’ve fought for criminal justice reform for over 30 years. We cannot let go of this opportunity for progress. If we align on this one issue now, we will give those who are rehabilitated a path to freedom.”

That’s certainly one way to look at it, but Jones—who Tweeted that Trump was “on his way to becoming the uniter-in-Chief on an issue that has divided America for generations” by supporting the First Step Act could be assessing the situation through rose-colored glasses. While the First Step Act is the most significant prison reform agreement Congress has passed in years, it will only impact the federal prison system. According to the Bureau of Federal Prisons, there are fewer than 181,000 federal inmates—a small fraction of the U.S. prison population. (And only a small number of them would be eligible for early release under the First Step Act, anyway.) Anyone skeptical has good reason to be.

First Step has allowed Trump to tout prison reform as a legislative victory for his administration. During last week’s State of the Union address, he trotted out Alice Marie Johnson, who he pardoned last year at the urging of Kim Kardashian, and Matthew Charles, reportedly one of the first people freed under First Step (and who Trump could have pardoned sooner). But there are plenty of Alice Marie Johnsons, plenty of Matthew Charleses, and plenty of Meek Mills who don’t have the privilege of celebrity to amplify their circumstances. It’s hard to say you genuinely care about criminal justice reform if it only matters when an entertainer goes to prison or alerts you of someone who shouldn’t be there.

Meek Mill and Robert Kraft, January 2019 (Kevin Mazur/Getty Images for The Reform Alliance)

Meek Mill and Robert Kraft, January 2019 (Kevin Mazur/Getty Images for The Reform Alliance)

The use of black people for nefarious photo-ops and as pawns is a go-to in Trump’s playbook. Despite whatever they may think, he stands to gain more from the association than they do. (He’s been doing this with rappers for decades, now.) In a piece for Rolling Stone, Jamil Smith notes that Trump pardoned boxer Jack Johnson posthumously, following advocacy from Sylvester Stallone, sought to vacate Muhammad Ali’s conviction for avoiding the draft, and has been advised to pardon the black nationalist leader Marcus Garvey by consigliere Roger Stone. This sure looks like strategic symbolism, given his track record.

Meek Mill was scheduled to participate in a panel discussion about prison reform with Trump at the White House last year, but ultimately chose not to attend. TMZ reported that JAY-Z talked him out of it, but Meek later released a statement to Rolling Stone saying he made the decision on his own after growing uncomfortable with the arrangement. “Unfortunately, the focus turned to the President and myself, which concerned me that it might take away from creating a positive result from today’s discussions,” he explained. While that situation presented a red flag for Meek, that apprehension doesn’t appear to extend to his association with Kraft.

Perhaps Meek, along with JAY-Z and Cardi B (who reportedly donated money to REFORM), believe the issue of criminal justice reform itself matters more than the optics of allegiance with a billionaire Trump supporter whose politics largely oppose their own. Maybe they, along with Jones, believe their efforts will be more effective if they involve someone who has Trump’s ear—and just so happens to be wealthy and white, as he is. Maybe that’s what REFORM’s call to action, #FightDifferent, truly means: Battling alongside unlikely allies, scrutiny be damned. For what it’s worth, the Pennsylvania Senate recently introduced a bill inspired by Meek’s case that would cap probation at five years for felonies and three years for misdemeanors, shorten probation in exchange for good behavior, and check judicial discretion in the instance of technical violations.

But one should also consider that Kraft’s relationship with Meek and place in REFORM could serve as a convenient smokescreen for Kaepernick’s case alleging the NFL colluded to blackball him from the league. Remember that Kraft was deposed by Kaepernick’s lawyers last year; maybe it’s a little harder to argue that owners conspired to keep him out of the NFL if one of them is part of a group championing a cause related to Kaepernick’s. But no matter how anyone positions the alliance, the contradictions are simply too glaring to take any explanation at face value alone.