76ers Co-Owner on His Jail Visits with Meek Mill: 'Hopefully He'll Be Home for Christmas'

Meek Mill
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Meek Mill performs during V-103 Live Pop Up Concert at Philips Arena on March 25, 2017 in Atlanta. 

Billionaire businessman Michael Rubin has visited Meek 4 times and praises the rapper's positive spirit.

The set-up sounds like the premise of a hilarious 1980s Eddie Murphy fish-out-of-water comedy: a billionaire businessman and NBA team owner befriends a gritty street rapper who can't seem to keep his nose clean enough for a tough-justice judge. The rapper goes to prison for what appears to be a questionable probation violation and the billionaire vows to do whatever he can to get his friend free by Christmas.

Except, in this case the story is very real and the rapper, Meek Mill, is running out of time to get sprung in time for the holidays. Billboard spoke to the real-life billionaire of this modern fairy tale, Philadelphia 76ers co-owner Michael Rubin, who tells us all about his unlikely friendship with the rapper and his mutiple jail visits with Philly-bred Mill (born Robert Williams), 30, since the "All Eyes on You" MC was sentenced to 2-4 years in prison last month for a probation violation; Mill was recently denied bail again

"His spirits are about as good as they could be in jail," says Rubin, who made his most recent trip to see Mill last Thursday (Dec.14), where the odd couple again spoke about what's next in the MC's case, their families and all the good vibes coming from around the country as part of the #FreeMeek movement. "He's smiling, he's positive and he's really very appreciative of all the support he's gotten... from Al Sharpton, Colin Kaepernick, Kevin Hart, all these people supporting him on social media."

To hear Rubin tell it, the story of how he ended up in a noisy prison visiting room seeing his friend for the fourth time in a month to talk legal strategy is about as unexpected as the sentence that landed the rapper where he is today, serving his third prison bid for the same 2008 conviction. "We met four or five years ago at an NBA game when my daughter and I sat next to him and his ex, Nicki [Minaj], and once he figured out I was one of the owners of the Sixers and some other pretty big, internet companies he started asking me 1,000 business questions, 'How do you do this?' 'Why'd you do this?' 'Did that work out?," Rubin says of the spark that lit their now-close relationship. "I liked him. I would have had the stereotypical view, this guy is a hardcore rapper... I didn't know who he was or what he did. But once he started telling me about his career I thought he would have an interesting business." 

Rubin, a serial entrepreneur who has built and sold a number of businesses for hundreds of millions after admittedly "barely" making it out of high school using "pure streets smarts over book smarts," says he was attracted to Mills' scrappy, go-getter attitude and the two bonded as casual friends thanks to Meek's die-hard Sixers devotion. Over the past 2-3 years, though, Rubin says Mills became among his closest male friends and they grew to mutually appreciate their different world dynamic, learning about each other while hanging out. 

And then, over the last year or so, they would talk on the phone almost every day for a few minutes, often late at night, or run into each other at Sixers games or events as their friendship grew. "Today I consider him to be one of my closest 10-20 guy friends, someone I really care about, someone I believe in, someone I think has a great career ahead of him," Rubin says. As they got closer, Rubin describes how Mill kept telling him stories about the judge who was handling his probation case, and as the summer rolled around the Sixers boss wondered by his friend was hanging around Philly so much and not hitting the road to promote his Wins & Losses album and support his family by playing shows.

"He explained the judge wouldn't let him travel and I didn't understand how he was doing that with all these people that depend on him," he says. "That's when I started paying attention to his legal situation and started trying to help." Mill is in a state prison cell after a judge said he violated his probation from a 2008 gun and drugs charge by failing a drug test and not complying with a court order to restrict his travel as her basis for his sentencing. He's received some vocal support from former 49ers quarterback Kaepernick and his label boss, JAY-Z, who addressed the situation last month from stage where he decried the slow changes to the criminal justice system.

But it was Rubin who went to court the day when Common Pleas Judge Genece Brinkley went against the no-prison recommendations of the probation officer and the assistant district attorney handling the case to sentence Mill to 2-4 years in prison. "I asked one of his lawyers how often that happens," Rubin says of his shock at the harsh sentence handed down that day. "He said 'never.'" 

Meek's attorney, Joseph Tacopina, has floated other reasons for why he believes his client is locked up. "She's enamored with him," Tacopina told Billboard last month of Judge Brinkley. "She showed up at his community service for the homeless people. She showed up and sat at the table. She's a judge. You could pull any judge in America and ask them how many times they've showed up at a community service for a probation and the answer is zero." Brinkley has not responded to Billboard's requests for comment on Tacopina's claims, which also include his assertion that she requested his client re-record a Boyz II Men son and shout her out in it and that he leave JAY-Z's Roc Nation to sign with her friend's label.

Seeing his friend getting what he thinks is a raw deal, Rubin has vowed to do whatever he can to help. "I thought I was watching a movie," he says of his shock at Brinkley's demeanor in the courtroom. "The whole thing was surreal. You're talking about a guy who's built a multi-billion dollar business multiple times... I come from a world of honesty and integrity and I witnessed what I consider to be as bad an abuse of power as I've ever seen. And at that point I said to Meek that myself and others will do everything we can to support him... Hopefully he'll be home for Christmas." 

Rubin can't get into specifics about what he's done to help Mill, but he says he'll do "everything within my power," using all his resources, to get his friend out of jail. That begins with the handful of jail visits, something Rubin is not afraid to say are a first for him. On one of those visits he was joined by the Sixers' Center Joel Embiid, who he said we even more terrified than he was to step foot in the lockup. "Meek is in as good spirits as anyone can be in jail. I think there's a lot of people who've stepped up to help him, but I'm surprised there are some people who haven't done more. Because to me this should be one of the biggest national stories out there." 

With his future uncertain, Rubin says Meek is working out, watching TV and trying to pass each day with a positive attitude, though it was unclear if he's working on new rhymes right now. "He's not mad at the world, he knows he's just been dealt a rotten hand," Rubin says. "He's very positive, I just can't believe Meek is in jail for popping a wheelie on a closed street where he was filming a music video and for breaking up a fight he didn't start and all the charges were dropped against him," Rubin adds about the two parole violations -- reckless driving and a fight -- that Meek pleaded out of and performed community service for.

"This is a great example of how broken the criminal justice system is," he says. "He's been on probation his entire adult life... he will have been on probation for 16 years. I couldn't be on probation for 6 years. If you're  5 minutes late for a meeting with your probation officer they can put you in jail. I feel confident he's going ot be home soon and this is a great injustice that's going to be fixed." 

Given the level of enmity Rubin displays for the judge in the case and his unwavering support for his friend, it's clear that the Sixers boss has skin in this game. How much becomes apparent when he tells a very personal story of how Meek's imprisonment has affected his family. "Meek's a great guy and I've only known him for the past couple years, so I can't speak to what he was like when he was 18," says Rubin, who has someone in his office compile the latest clips about Meek's case and send them to the rapper every day.

"But I can tell you the day that the hearing happened I spent 6 hours in the courtroom and I came home and my daughter looked at me... I don't think she's ever seen a tear come out of my eyes, she said, 'dad are you okay?' My daughter's eleven and a half years-old. She said, 'wait a second, what happened with Meek?' I said, 'don't ask.' She said, 'dad what happened?' So I told her and that night at two o'clock in the morning she comes in my room and says, 'daddy, if I get bad grades in school will I get taken to jail?' I said that's ridiculous. 'But if he got taken to jail for what he did why couldn't they take me to jail for having bad grades?'" 

And then she looked at her dad and said, "Daddy, you better help him" and I said 'of course I'm going to.' Every day when she gets home from school she asks 'is Meek out of jail yet?' Every morning when she gets up she asks, 'is Meek out of jail yet?’"