An Unfiltered Conversation With Meek Mill

For Robert Rihmeek Williams, it begins and ends with the dirt bike. They appear constantly in his music, his videos, he’s built a business around the passion, and one once indirectly sent him to jail. You could say the refrain of his life has been the unmuffled roar of a 125cc bike motor. One blares through the intersection of 18th Street and Berks, a young kid popping a wheelie, unconcerned with stop signs or a helmet.

I’m here at this intersection in North Philly, hanging out and taking notes on a Sunday afternoon, because I’m trying anything I can think of to get closer to Meek Mill. I arrive in Philadelphia several hours before he is set to headline Roots Picnic 2025. I grab my press pass from the Logan, a luxurious hotel off a traffic circle in the heart of Center City, and I drive north.

The ride doesn’t take long—it's 13 minutes. As you traverse the narrow, single-lane streets with parked cars lining both sides, it feels like you’re making a trench run to drop off a payload. The buildings change from large, amenity-packed apartment complexes and hotels that take up entire blocks, to alternating run-down row houses and white-picket-fenced single-family homes that appear to have been uprooted entirely from their square of land in the suburbs and deposited in North Central Philly. The traffic becomes sparse, the cars older and fucked-up, with tarps over the sunroofs and dented fenders that need to be banged out. The sporadic pedestrians and people hanging out on stoops and bored kids hanging out of second-story windows go from a diverse mix to predominantly people of color.

Meek has long claimed 18th and Berks. It’s a core piece of his mythos—where he struggled growing up and where he battled, lyrically and physically, soaking up the game that would make him a millionaire artist who frequently rubs elbows with billionaires. And, just a few miles away, he’s coming home to headline his city’s signature festival for the first time. It’s a coronation. The prodigal son returns.

Later that night, in Fairmount Park, Meek hits the stage wearing a Phillies hat and several chains bearing envelope-sized, jewel-encrusted Dream Chaser medallions. Midway through his set, he teases his most emblematic song, 2012’s “Dreams and Nightmares.” Those drumless, rolling piano keys drop, and Meek asks the crowd—as he has hundreds of times before—“Ain’t this what they’ve been waitin’ for?”

It’s a feint. Meek is cut off by fellow hometown heroes, podcasters Gillie and Wallo, who lead the crowd in a flapping chant of “E-A-G-L-E-S EAGLES!” before they demand Meek go back and play “the old shit” from his mixtape years. And he does, still rapping as he did back then, like he’s on a poorly lit street corner with his credibility on the line surrounded by goons who will whip his ass if he doesn’t put everything he has into the next verse. His couplets are torqued up, indignant, and always delivered with a catch in his throat, holding back tears or rage or both. Every bar ends with an exclamation point. “It felt great to be back in my city,” Meek would tell me two days later during a phone conversation. “I love to be in Philadelphia. I love to be backstage with the guys, the movers and shakers, people I grew up with in the studio, and just grew up with here.”

The Roots Picnic crowd is a mix of grown-and-sexy flower children, aunties, true-school hip-hop types and menswear podcast guys. But what this crowd has in common at the moment is they’re all going nuts rapping every word to Meek’s “Rosé Red” off 2010’s Flamerz 3. The Legendary Roots Crew’s lead vocalist, Tariq Trotter, or Black Thought, who helped book Meek for this set, later explained to me Meek Mill’s Rocky narrative in rap form, why his intimate connection to Philly remains so powerful. “Meek has become the voice of a generation of young Philadelphians, especially young men who feel or have felt unseen” Thought tells me. “They feel like the Meek Mill story is my story. It's the story of Philadelphia. The story of Black people. Get it from the mud, through the struggle, through tragedy, and persevere.”

And yet, thinking back on the performance, I sensed a certain ambivalence coming from the stage. At times, the tenor carried a distinct sour note. Meek barked between songs, urging love and positivity, wrapped in the anger of a kid who made it through adversity but resents that struggle and the scars it left. “They told me my career was over 10 times, we still here going the fuck up in Philly,” he barks between songs at one point. “When I was locked up the internet didn’t support me, my city did.”

Fifteen years into his career, Meek Mill is at an inflection point. Now independent, he’s experiencing a creative resurgence, delivering some of the best verses of his career in recent collaborations with G Herbo and rising artists like Kocky Ka and Fridayy. This momentum is undercut by a frustrating reality: Despite his accomplishments, Meek is often targeted on the Internet—mocked, in part, for his association with Sean “Diddy” Combs, who has spent the last month standing trial on federal racketeering and sex trafficking charges. (Diddy was acquitted of sex trafficking and racketeering but found guilty on lesser prostitution charges.)

In February 2024, Meek was indirectly pulled into Rodney “Lil Rod” Jones’ $30 million lawsuit against Combs. Meek, referred to therein as “a Philadelphia rapper who dated Nicki Minaj,” catches a stray, accused of no illegal activity but alleged to have had sex with Combs.

It's a confusing situation. There is no clear motive for involving him, though Meek has theories. “I truly believe it is a group of people aiming to tear down rappers, or Black entertainers involved in this culture through media platforms,” Meek tells me. He sets up a hypothetical, trying to explain the threadbare, flimsy nature of “truth” on the internet. “There was never a way people could just put out one rumor, and say I raped a little girl … Now it’s in 15 publications that I raped a little girl. That’s defamation on any level, but it’s the way with social media and the internet.”

Many of the charges in the suit were thrown out by Judge J. Paul Oetken in March (allegations of sexual assault against Combs remain). Meek is quick to point out that while news of the allegation blew up, the response to the dismissal was relatively muted. Jones’ lawyer, Tyrone Blackburn, is currently being sued by Fat Joe for extortion after bringing a similarly salacious lawsuit against him. Blackburn’s tactics echo the recent strategy of Tony Buzbee, who has filed noisy cases against Diddy and Jay-Z, some of which have already been dismissed outright.

In his dismissal of several charges, Oetken rebuffed Blackburn for “inappropriate ad hominem attacks,” “irrelevant insults,” “misstatements,” and “exaggerations.” But Meek’s “unnamed” and improper inclusion had the presumably intended effect of making headlines, calling attention to the suit, stirring embarrassing conversation and a torrent of memes around the rapper and the alleged relationship.

When conducting an interview of this nature, I like to arrange my questions based on degree of sensitivity. The plan was to save Diddy for the end of our conversation. I bring this up because within 15 minutes of our conversation, unprompted, we were hashing out the particulars of the case and Meek’s history with Diddy in detail.

According to Meek, he first met Diddy in 2013, and their relationship developed through musical collaboration. As for the explicit details now central to the legal case—the white parties, the drugs, the so-called “freak offs”—Meek claims he wasn’t present for any of it.

“When I come around from Philadelphia, I always come around with three, four people. I’ve never been in these types of environments without my guys around. A lot of people, they said sex parties. I attended New Year’s parties. I never attended [Diddy’s] white parties,” Meek said. “It’s kind of suspicious to me that none of those people from the Black community never spoke up and said those parties they went to wasn’t straight freak offs. I can just say, for me, I would never step in anywhere that I see anything that doesn’t align with my morals.”

There is a general suspicion shared by Meek around how the allegations have been handled publicly. The implication is that this is more than just a lawyer exploiting a tenuous connection for headlines. “My credibility and my morals as a man has never been questioned in reality,” Meek tells me. “The moment that a random goofy guy files an anonymous lawsuit… a lot of publications picked up that story in a certain way, which led to millions and millions of comments that was 20% real people, 80% bots that were funded.”

Last September, Meek posted on X (formerly Twitter) that he wanted to put $100,000 toward hiring a private investigator to find out how and why he was dragged into the Diddy scandal. The post was widely mocked, flooded with derisory quote tweets. But Meek tells me he was dead serious.

“I am the one kid from the ghetto that motivated the ghettos of America, and I have a special relationship with a lot of powerful billionaires. And now all this new press is coming, and this wasn’t going on when I was in the hood, playing with guns, throwing my life away, and trying to sell some weed,” Meek said. “So I just want to get to the bottom of this, and learn how not to let it happen to me again.”

He is emphatic in denial of the allegations, to the point he sounds desperate to find a way to prove beyond a shadow of a doubt it’s bullshit. “I’m being literally up front about it, talking about it in the open while [Diddy’s] on federal trial to make it known that I am not affiliated with Puff Daddy’s sexual life or personal life and never have been,” he says.

As for Diddy’s (then) impending verdict, “Puff is fighting a life sentence. I'm the first Black man to speak on this. I don't think he's right about nothing I've seen, nothing that he's involved with with domestic violence or anything,” Meek says. “But I'm a Black man. If I see another Black man fall, I am not here to laugh, and I don't want to see you fall any harder. You handle your responsibilities for your choices you make. Just because you made mistakes, I don't want to see any Black man die in front of my face.”

Meek refers to his reputation being under attack frequently during our conversation, almost always at the hands of “the media.” I ask him to distinguish whether or not he means actual media or the trolls posting random pictures of him, Diddy, and Peter Dinklage on their timelines. He explains what many of us fear—that for most people, this distinction no longer exists. “When we speaking on information, a lot of our generation now are getting our information from these phones,” Meek says. “So a social page or a podcast is the same as TV.”

Protecting his reputation is of vital importance to Meek, and he has employed X as the bullhorn to do that. The app has a large role in Meek’s history. It’s allegedly how Rick Ross first discovered him. During a tour stop in Philly, Ross polled his followers for some local artists he should work with. The response was overwhelming.

“I’m from the corners of North Philadelphia. If I can speak to people in Africa, China, and Asia, I don’t think I’m ever going to stop using Twitter,” Meek says. “I was brought up in a community where people told you don’t ask questions, don’t really talk, be timid. If you grew up in my community like that, you won’t survive, so I think you should always keep a voice alive.”

Despite his commitment, Meek has a contentious relationship to the app that can border on detrimental. I told a random couple I met at a bar last week that I was working on this story. They replied by freaking out and showing me a meme made of an infamous Meek tweet about the word “neurodivergent” that has become a kind of in-joke shorthand in their relationship

That post was actually a quote post, which helps identify the issue. X can be a dangerous medium if you’re a wildly famous artist weighing all traffic equally and responding to as many trolls as Meek engages with. It has led to less-than-great moments for him online, a perception he acknowledges. “Sometimes I’ll just [post] a bar to a rap, and they be like, ‘Meek slow, what is he talking about?’ I’m not here to explain to the internet what I was talking about. When we talking rap, we don’t speak in English text.” Meek says. “We got our own languages. We’re talking how we want.”

In a country filled with people who desperately need to spend less time on their phones, Meek strikes me as someone who needs to log off for at least a little while. (During our interview he angrily referenced a rumor about a rapper being gay that I didn’t ask about, had never heard before, and couldn’t give less of a fuck about.) “It’s all perception,” Meek tells me, and you can tell he believes this. The impression he leaves is of a reasonably sensitive person entirely too invested in how he's perceived by the internet’s millions of low-comprehension readers and bad-faith actors.

In the late 2000s, on the cusp of the local fame that would come with his first Flamers mixtape, Meek was arrested based on police testimony and circumstantial evidence. He’s convicted of simple assault, possession with intent to deliver, and a gun charge. This would mark the beginning of a long and contentious relationship with Philadelphia judge Genece Brinkley. Meek’s sentenced to 11 to 23 months in county jail—serving five—followed by house arrest and seven years of probation. From there, Meek’s life becomes a cyclical nightmare. As he blows up, there’s a litany of jail stints, and house-arrest stints, and mandated community service, and mandated etiquette courses for “violations” like unannounced travel and missing drug tests. Shawn Gee of Live Nation, who has known and worked with Meek through local Philly charities for years, had served as a character witness for Meek at one point in the 2010s, but couldn’t remember the exact incident that necessitated his testimony due to the sheer number of them.

This comes to a head in 2017 when, eight years into his probation, Meek was sentenced to two to four years in prison by Judge Brinkley for, among other things, being filmed popping a wheelie on a dirt bike in New York with no helmet on. This sparked national outrage and the initial “Free Meek” movement, which then unleashed ripples that spread far beyond his dedicated fanbase.

The story was so egregious and disturbing, it miraculously struck a chord in our horror-filled, screen-numbed country, bringing billionaire sports franchise owners and Jay-Z to Meek’s corner. When I spoke to Meek, I asked him how this proximity to billionaires has changed his outlook on life. His publicist interjected and informed me I was asking the wrong question: “It’s Meek who changed the way these billionaires look at the world.”

When I was knocking “House Party” on the West Side Highway with the windows down in the 2010s, I, nor anyone else, would have been able to see this outsized role as one of rap’s most political figures coming. Meek has become a symbol and an individual who isn’t resting on his laurels as a symbol, but is actively fighting the good fight on behalf of his community. With the aid of some of those billionaire friends—notably Michael Rubin and Robert Kraft and Jay-Z—Meek established REFORM Alliance in 2019, a non-profit organization with the unique, hyper-focused mission of transforming probation and parole. They are currently some of institutional racism’s most devastating, draconian drivers of incarceration, and Meek hopes to save others from the hell a full decade of his life was.

“In five years, I think we will change the way the system operates.” Meek says. “We're trying to provide resources, change statutes and laws, so this doesn't continue to grow as a problem, because we all know that the system that's in place has not been working for Black and brown culture.”

Jessica Jackson is the Chief Executive Officer of REFORM. She met Meek in 2017, shortly before the Free Meek saga began. “When Meek came out [of prison], he could've done anything, but I think what was so amazing is he wanted to help people who don't have the resources he had to get out,” she says.

REFORM has helped pass probation-related legislation in 12 states, including those as politically different as California and Mississippi.

Jackson says Meek is far from just a figurehead in the organization. He’s been boots-on-the-ground and hands-on since day one. “I probably talk to him once a week, if not twice a week,” she said. ”He joined us on a legislative call with the Lt. Governor of Virginia when we were trying to pass the bill there recently. What he does behind the scenes really keeps us grounded in the community. He's always bringing us new cases, amplifying our efforts, helping us share stories of people who have been impacted, and he's even been really helpful on the legislative side whenever we need him in a meeting—which he's always willing to do, whether it's a Republican or Democrat.”

When I spoke to Meek, it was the week after Donald Trump had issued the pardons or commutations of over two dozen people, with some high-visibility prisoners that included YoungBoy Never Broke Again, Death Row Records co-founder Michael Harris, and the famed Gangster Disciples leader Larry Hoover. It was clearly a cynical move for approval, freeing a few token figures while engaging in policies that continue to kill, oppress, and withhold resources from communities of color. But it was also objectively both a good thing to do and smart policy, politically.

I asked Meek if he thought Democrats had anything to learn from this sort of cheap showmanship. “I like when Trump do that. I'm not really in politics, but I love when anybody at a presidential level show anybody that comes from the Black hood, the ghetto community, any type of love or attention, because we have been buried so long,” Meek says, untinged by partisan divide and political agenda, motivated exclusively by how the issue at hand affects his community. “One day, if I ever meet Trump, I would like to bring him to a prison and teach him about Black culture, the things they saying he's racist about, I would like to introduce him to that shit.”

After nearly two decades as a nomad, moving through label drama and management, Meek is coming off what was essentially a distro deal with Virgin Music Group. It was a logical decision after decades of what he views as mishandled promotional campaigns, and bad contracts stuffed with funny math. As a main point of contention, he points to how the rollout of his mixtape DC4 in 2016 was handled in the shadow of the Drake beef.

“I can't wait till the UMG Drake lawsuit plays out because I want to learn the game. I want to see how it was worked against me,” Meek says. He was at Atlantic Records when the beef with Drake popped off. In retrospect, it mirrors the beef Drake would eventually get himself into with Kendrick Lamar. Meek suggests his own label had a finger on the scale, perhaps skewing Drake’s conception (or teaching him) how “these things” are supposed to work when the game isn’t rigged. “[Atlantic] told me it wasn't a good time to drop an album, so I went against the advice and dropped a mixtape.” (Which sure sounds reminiscent of the experience Pusha-T recently revealed he’d experienced in his own subsequent beef with Drake).

Working on a severely limited budget and coming off “a loss,” Meek assembled an all-star team including Nicki Minaj, Lil Uzi Vert, Quavo, Young Thug, and Pusha-T to contribute verses for free. The project debuted at No. 3 on the Billboard Top 200. But after all that, “[Atlantic] didn’t count it as an album,” Meek says, meaning the label didn’t take a project Meek owed off his seven-album deal.

“My whole life was caught up in systems. Prison systems, industry systems,” Meek says. “This time I’m independent.” He is now less regimented in his creative process. He’s always in the studio, but it’s not necessarily in service of a specific project. He’s been working with younger artists he inspired, like the young Philly-bred artists Skrilla and the aforementioned Fridayy. “Meek the OG still playing. He like LeBron [James] right now,” says Skrilla, who is from Kensington. “Working with Meek makes me feel like I'm doing something right.”

G Herbo, who has collaborated with Meek twice in the past year, says Meek was his favorite rapper growing up. To this day, Herb is one of the clearest descendents of his gritty delivery, largely by design. “I wanted to basically mimic my style in career based off of what he did. He was freestyling and doing battle rap as a teen. It's not easy for a battle rapper to actually become a real global superstar. It was crazy,” Herbo says. “He is still an MC at the end of the day, with real lyrics, and there's never been a battle rapper that has had the success that Meek Mill has hit.”

It can be viewed as an approach to the streaming era, making one-off swings at hits with younger artists, trying new things and ideally expanding his base, introducing himself to younger listeners, but for Meek the key is ownership, both for himself and for his family. “It's the grand strategy. I got two sons. I got plans on putting these catalogs in my sons’ name,” he says. “If the song makes millions, I never touch the account. And I just start a new way of life, you know? If I make 300 songs until the day I die, it's in my family name, and they’re able to make money every quarter and not have to worry about going check to check.”

Another core tenant for Meek is #BikeLife, the loose community he’s formed that has involved an app, YouTube videos, organized bike outings with other enthusiasts, and lobbying with politicians to ease restrictions on dirt bikes and ATVs, as well as fighting for dedicated spaces for them in cities. Meek views the sport as in the same place skateboarding was in the ‘90s, with the same potential to build bridges and break down barriers of race and class. He has dreams of turning Bike Life into a company, and that company being the thing that makes him a billionaire.

I know this because an hour and a half past our allotted time, as we said goodbye, I apologize that we never got to talk Bike Life, and Meek immediately perks up, insisting, “Nah, let’s do Bike Life real quick. That’s one of my major loves.” His voice changes as we talk about bikes for five minutes. The edge and all the resentment falls away and I realize it’s because for the first time in almost two hours, we’re discussing something he actually enjoys talking about.

For my final question, I ask Meek, after the ordeal they caused him, what bikes represent to him—in life, in general. And he explains how for him, it’s a brief separation of mind and body, a respite from the anxieties, fears, and insecurities clouding his brain, trained through decades of trauma. That they grant him a fleeting measure of peace in his life as a Black man that this country never afforded him. “When you’re on your bike, doing your tricks and hitting the brakes and clutches? You’re taking your mind away from the depression,” he says. “It’s freedom. I feel free.”

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