City

How Michael Rubin, Meek Mill’s Billionaire Bestie, Got Woke

The Lafayette Hill native’s path from e-commerce titan to Sixers co-owner to social justice crusader.


Photograph by Chris Crisman

“Did you see what’s on his phone? That’s the most pathetic thing I’ve ever seen.”

Michael Rubin is wrestling with Joel Embiid in a losing attempt to steal the Sixers center’s iPhone and embarrass him about a particular snapshot Embiid is using as his home-screen pic. Or, to take a broader view, a billionaire businessman and a millionaire NBA All-Star are goofing around like 13-year-olds. We’re in a five-seat AW139 Agusta helicopter that picked us up at Rubin’s office in Conshohocken for a trip to Foxborough, Massachusetts, where Rubin, two business associates and Embiid will be guests of Patriots owner Robert Kraft for a preseason matchup with the Eagles. Embiid loves football, but he was mostly just up for a night out with Kraft, arguably the most powerful man in the NFL, and Rubin, who’s both his boss and his buddy. Embiid is rocking gray sweatpants, a white hoodie and suede Saint Laurent kicks; combined, the cost of the outfit probably exceeds my monthly rent. By contrast, Rubin wears Nikes, a charcoal tee, and jeans that are surely designer but could pass for the dad variety.

At 46, Rubin may not look the part, but he’s in peak baller mode — taking his heli to a game, then skipping over to the Hamptons for a weekend with Kraft and their girlfriends. Rubin is also a personal friend of Jeffrey Lurie, so it’s fortunate that tonight’s contest is meaningless, with no real rooting interests. The Super Bowl was a different story. If Rubin hadn’t needed to go there for business — his sports merchandise company, Fanatics, throws one of the biggest parties in a week that’s full of A-list blowouts — he would have avoided it.

“It was complicated,” he says. “Look, I love Jeffrey. Howie Roseman is my buddy. I’m friends with a bunch of guys who play on the team. But you can’t have one of your closest friends and then abandon them. It would be wrong.” The friend he’s referring to is 77-year-old Kraft.

“I generally don’t have a lot of fandom outside of the Sixers,” Rubin explains. “Fanatics takes the fandom out of you, it really does. You’re actually rooting for whoever makes you the most money.”

Such is the stuff of sports-talk-radio outrage: One of the Sixers owners cheers for the Pats? Boycott that crumb bum! But Rubin is a businessman to his core, hardwired for commerce in a way that’s different even from nearly anyone else who’s achieved this level of success. He’s been hustling since he left for sleepaway camp, a college dropout who’d been sued and gone virtually bankrupt before he could even vote. He’s also a true visionary — Rubin saw the potential for online retail while the rest of the world was still living the brick-and-mortar life and built GSI Commerce, a multibillion-dollar business. Now, his second 10-figure empire, Kynetic, consists of three e-businesses, including the crown jewel, Fanatics, which designs, manufactures and sells merch for all four major sports leagues and others to the tune of $2.3 billion in projected revenue this year. “It’s amazing,” Kraft says. “He’s basically built a mini-Amazon in sports merchandising. He used his vision and drive to develop a niche. He saw it before everyone else.” Did you buy a Ben Simmons tee for the Sixers’ playoff run? Do you own a Rhys Hoskins or Shayne Gostisbehere jersey? Eagles Super Bowl LII championship hoodie or jersey, underdogs tee, or autographed “Philly Special” framed photo? Fanatics made them and sold them to you.

“He’s an amazingly intense person and an amazingly competitive person,” says Josh Kopelman, founder of First Round Capital and a longtime friend of Rubin. “He’s probably one of the best strategic people I know in terms of playing chess when everyone else is playing checkers.”

Until recently, Rubin — with a net worth hovering around $3 billion — was among the most low-key Philadelphians on the Forbes 400 (number 278 on the 2017 list, 14 spots behind Phillies principal owner John Middleton and 110 ahead of Lurie). His role as the third largest shareholder in the Sixers raised his profile, but unless you’ve seen him courtside with Kevin Hart or Lil Uzi Vert, you probably couldn’t pick him out of a lineup or a paparazzi photo on TMZ Sports (though you may have read the news this summer that he purchased one of the most expensive penthouses ever sold in Lower Manhattan, for $43.5 million).

Rubin with Kevin Hart, Robert Kraft and Meek Mill just after Mill’s release from prison. Photograph courtesy of Michael Rubin

But Rubin’s public persona — and his life — has changed, thanks to his friend Robert Rihmeek Williams, a.k.a. North Philly rapper Meek Mill. When Mill was sent to prison last November, Rubin mobilized — launching the Free Meek campaign with Jay-Z and taking aim at not only the judge handling Mill’s case, but the entire criminal justice system. The luxe chopper we’re riding in is the same one that famously picked up Mill from jail in Chester and flew him straight to a Sixers playoff game in April.

Tonight, the activist/entrepreneur/ billionaire is focused on the fun stuff, like breaking Embiid’s stones constantly. Despite the nonstop clowning around, business is never far from Rubin’s mind, and neither is the cause he’s championing. His rise from business prodigy to sports mogul and Sixers owner is a story in itself. But then Meek Mill went to jail, Michael Rubin got woke — and a new chapter in his life began.

A few weeks earlier, Rubin greets me in his corner office at the Kynetic headquarters in Conshohocken for our first interview. He’s dressed summer-Friday-afternoon ultra-casual, in white cutoff denim shorts, a gray t-shirt and leather sandals, and flanked by his partner and his corporate PR chief. The “office” next to his is a playroom for his 12-year-old daughter, Kylie — it’s a concept he borrowed after talking to another CEO who wanted to find a way to stay close to his kids even when he was working, which for Rubin is seemingly always. While he flies to his Manhattan office weekly, his empire was built within seven miles of where he’s sitting, and staying close to his family is a priority. He lives minutes from his ex-wife and spends a few nights each week with his daughter, who inspired his company’s name; his mother visits his Bryn Mawr manse for dinner on Sundays. Rubin has a quick answer for how a kid from Lafayette Hill ended up becoming a titan of e-commerce: “I think you’re either born with the entrepreneurial bug or you’re not. I was a shitty athlete. I was a bad student. I wasn’t really good at anything other than business. Ever since I was old enough to make money, I wanted to do that.”

You’ve probably read stories about entrepreneurs who opened lemonade stands and whose proud parents instantly knew they were destined for big things. That’s fairly normal — a word no one would use to describe Rubin. Sure, he got into snow shoveling at age 10, but he didn’t break a sweat; instead, he rounded up five kids and paid them to do all the manual labor. Around the same time, his mother, Paulette, a psychiatrist, was cooking dinner one night when she overheard him on the phone with a friend of one of his two older sisters, asking about the teen’s baseball card collection. When her husband, Ken, came home, she asked, “Do you know how Michael knows what ‘consignment’ is?” Later, she gently informed her child that his plan to sell the cards at his sleepaway camp was flawed, since the other campers wouldn’t have any money. “I’m not selling to the kids,” he said, as if his intentions should have been obvious. “I’m selling to the dads on visiting day.” Sure enough, there was a line of fathers outside his bunk with cash in hand.

The rest of Rubin’s origin story is about as unbelievable as anything you’d see in a Marvel movie, if the superhero was a nice Jewish boy from Montco with a savant-like way of seeing the world. At age 12, he opened a ski repair shop in the basement of his parents’ house; two years later, his father, a veterinarian, co-signed a lease so Rubin could open his own store in a Conshohocken strip mall with $10,000 he’d made. Action News cameras captured a marketing stunt one summer as Rubin arranged to build a 142-foot ski slope in the parking lot with 45,000 pounds of ice. As a junior at Plymouth Whitemarsh High, the budding businessman would leave classes early through a co-op program to work at his shop.

It looked like Rubin’s career was over before it really began when he found himself in the red for $200,000 at age 16. He was being sued by a slew of creditors, who were stunned to learn that the hot shot they’d only spoken with by phone was a minor. Rubin hired a lawyer to settle his debts, got a loan from his parents, and eventually owned five ski shops with annual sales totaling $2.5 million. When his folks refused to lend him more money, he borrowed 17 grand from a neighbor for a new venture — buying closeout sporting-goods merchandise and selling it for a markup. Rubin’s parents made him agree to give college a shot. He lasted less than a year at Villanova. “For the first semester,” he says, “I was always in the parking lot with this giant phone — they were like a fucking brick at this point — and I’d be late to class because I’m buying something in Asia and selling it in England, wheeling and dealing like crazy.”

KPR Sports, the new business he named for his parents, led to the creation of an outdoor shoe company and a controlling interest in Ryka, a women’s sneaker manufacturer. At 23, the “Sneaker Stud,” as People crowned him, was generating $50 million in sales and preparing to build the next Nike or Reebok. But in 1998, back when Amazon only sold books, a Wall Street analyst asked Rubin what he was doing about the World Wide Web. “My first answer was, ‘Fuck this internet thing. Don’t waste my time. It’s all these young kids who don’t make any money. They all lose money.’”

The analyst persisted, and Rubin began polling the CEOs of all the sporting-goods giants he sold to about their plans for e-commerce. “They didn’t know how to do it themselves,” Rubin says. “If I could bring them to scale and do that myself … I saw the business opportunity.” Was Rubin at all afraid to tackle a business model with so many unknowns, including his own inexperience? “That’s what I think makes an entrepreneur,” he says. “I was probably too fearless then.”

To build Global Sports Interactive, Rubin needed funding, and a near-disastrous meeting in New York would change the course of his life. Masayoshi Son — CEO of SoftBank, a Japanese firm heavily invested in Yahoo and E*Trade — agreed to meet with Rubin and his small team, including Mike Conn, the analyst who pestered Rubin about the internet and then joined him at GSI. Rubin pitched uninterrupted for 30 minutes. Masa, as he’s known, responded by saying, “You’re the next Jeff Bezos and Michael Dell. I’m buying 30 percent of your company.” But rather than gladly taking any deal offered, Rubin began to grill Masa on SoftBank. “I was shaking,” Conn remembers. “I mean, our payroll was bouncing and Michael starts pushing back. I did the math, and this was an $80 million deal. There are many times in life with Michael when I wish I had a pause button — just freeze and say, ‘Wait a second.’”

Masa isn’t easily rattled, and eventually SoftBank closed the deal. Rubin’s ex-wife, Meegan, remembers another moment in the negotiation process, when she sat in awe during a dinner near Piccadilly Circus in London as her then-boyfriend and Masa — with input from another guest, Rupert Murdoch — worked out the details of their arrangement.

At the same time, Josh Kopelman created the e-marketplace Half.com in Conshohocken and found a kindred spirit in Rubin — two Philly founders during the late-’90s/early-aughts dot-com boom and the bust that followed. The two would meet for lunch at Rubin’s King of Prussia office or Stella Blu in West Conshy and talk shop about their increasingly fickle industry. One day in 2001, as GSI’s stock bottomed out at $3 a share from $33 two years before, Rubin spent a good portion of the afternoon curled up under his desk, contemplating his company’s collapse. “The mortality rate was high,” Kopelman says of the many ventures that folded. “It was a game of musical chairs. Michael and I were both lucky enough to have caught a chair before the music stopped.” (GSI’s stock rebounded within a few months.)

What set Rubin apart and set GSI on a course for unthinkable success is his long view, says Kopelman, who was briefly on GSI’s board: “What I see in Michael is an intense tolerance for delayed gratification. When you’re an entrepreneur, you’re sacrificing pain and suffering today for success later.” A key aspect of Rubin’s strategy was signing long-term deals, like an 18-year agreement with Sports Authority, at a time when anything longer than 10 years was unheard-of.

GSI grew rapidly, expanding across retail sectors by partnering with Ralph Lauren, Toys “R” Us, GNC and others. Rubin attracted a workforce of young, tech-savvy employees who were willing to work hard for relatively little compensation to be part of something big. Before he launched the Philly sports-gossip site Crossing Broad, Kyle Scott worked at GSI for two years, in the late 2000s. When the Phillies won the World Series in 2008, Scott was on wi-fi at a sports bar, updating the team’s and MLB’s websites; he estimates GSI processed a few million dollars in Phils-related revenue in 24 hours.

After narrowly surviving some heady days, including the internet crash and the Great Recession, Rubin made his next earth-shaking move in 2011, when he sold GSI Commerce, as it was then named, to eBay for $2.4 billion. Rubin and Conn celebrated with burgers and beer at Champps at the King of Prussia mall on a Friday. Conn thought maybe they should take a year off to contemplate the future; Rubin was back to work on Monday and already had a plan. eBay wanted Rubin’s B2B platform to compete with Amazon, but it didn’t need his consumer businesses. So Rubin bought three of them back — the designer fashion site Rue La La, the members-only retail site ShopRunner, and Fanatics, the licensed-sports-apparel behemoth. When asked why he didn’t just retire, Rubin answered in typical Rubinesque fashion: “I will work at the same incredibly hard pace until I die. I love it. I’m having more fun than I’ve ever had.”

Like his net worth, Rubin’s enthusiasm for empire-building keeps growing. Last year, he purchased the sports merch giant Majestic, and also flew to Japan to pitch his old friends at SoftBank — which now runs the world’s largest tech fund — for a new round of funding, walking away with $1 billion. With his eyes on expansion into European soccer and sports across Asia, Rubin predicts annual earnings of $10 billion in the next decade for Fanatics alone. He says his “v-commerce” model of vertical retail — designing, manufacturing, and selling merchandise directly to consumers — is what sets Fanatics apart and has helped him secure deals with the major sports leagues that average a whopping 15 years. “I feel like we’re just getting started,” he tells me. “Even though this has become a decent-sized business, we’re still in the first quarter of the football game.”

Sports are now threaded so tightly through all aspects of Rubin’s life that it’s impossible to untangle work from play, which is exactly how he likes it. His friendship with Kraft, his trips to All-Star games with his daughter or to the Super Bowl with his mom, partying with Embiid and Ben Simmons across the globe — he’s never off the clock, and business is never far away from the fun.

In the heli somewhere over North Jersey, I ask Rubin and Embiid what they have in common.

“I’m a great basketball player,” Rubin says, getting a laugh out of the fit professional athlete seated beside him. He has a slight middle-age paunch that contrasts with his boyish face. “Short, Jewish, out of shape — we have a lot in common. When did we start hanging out?”

“The first summer when I was hurt, not much,” Embiid says. “But the end of the season … I think it was in New York. We went out, and then we started hanging out.”

Rubin’s larger-than-life résumé and singular personality have a cinematic quality. Sportscaster Howard Eskin compares him to Russell Crowe’s character in A Beautiful Mind. On a personal level, Meegan Rubin jokes that her ex is Tom Hanks in Big — a child trapped in an adult’s body: “Michael definitely has a young vibe.”

His youthful exuberance is on display as Rubin and Embiid recall their trip to the Atlantis resort in the Bahamas to celebrate the birthday of a model friend, Jocelyn Chew, whose Instagram account was once featured by GQ. Rubin posted photos of a petrified Embiid at the top of a gnarly 60-foot near-vertical water slide and a video of his reluctant investigation of a lazy river as inner tubes filled with vacationers leisurely passed by.

“When you see someone who’s seven-foot-two and can’t swim in a two-foot pool,” Rubin says, “it’s kind of hard not to make fun of them. That was honestly one of the funniest weekends.”

“We had so much fun,” says Embiid. “I would do everything else except for the slide. The slide was awful.”

“The scary thing was, Joel uses his hands on the side of the slide, holding on. He’s going to lose a hand or a finger. You’ll be the only person to get hurt in the history of the NBA on a water slide.”

Rubin, Embiid and friends in Miami Beach for the Sixer’s 24th birthday. Photograph courtesy of Seth Browarnik/WorldRedEye

Rubin is a social media newbie, but with some editing advice from his daughter, he’s begun to document his personal life (or at least the “G-rated version,” as he says). Whatever he omits, Page Six or TMZ is likely to cover: Embiid’s 24th birthday in Miami Beach, attended by models of the Instagram and Victoria’s Secret variety, or Rubin waving a giant Sixers flag at his 46th birthday in Las Vegas with Simmons, Mill and Kraft. (Rubin is well known for having frequented Atlantic City and Vegas in his youth. These days, he plays private high-stakes blackjack.)

Rubin’s favorite subject for ball-busting at the moment is Embiid’s girlfriend, a successful model — a silly video and a romantic photo with her are constant sources of blackmail threats. Rubin prods Embiid to explain why he owes so much to their friend Chew.

“She’s the reason why I’m in love,” Embiid says with a huge grin, as Rubin and the business associates whoop it up.

“He took her to Cameroon!” Rubin yells, referring to a trip Embiid made with his girlfriend where she met his parents.

Embiid looks at me and deadpans, “He’s jealous.”

When talk turns to Rubin’s current flame, new media coordinator for Major League Baseball and model Camille Fishel, Rubin clams up. Embiid rolls video to capture Rubin’s response as the tables turn, and another wrestling match ensues. Rubin retaliates by raising the stakes for his threats.

“Twenty percent reduction in your pay,” he says. “We’re making free-agency room.”

It’s hard to imagine Rubin’s fellow Sixers co-owners, Josh Harris and David Blitzer, cracking wise about contract restructuring or popping bottles with their players. It’s also easy to jump to conclusions about Rubin’s joie de vivre. (Phone call for Mr. Rubin, midlife crisis on line one!) But Rubin had all the trappings of wealth decades ago; he had a Porsche before he had a driver’s license, and when he was 27, his garage housed a Range Rover, a Mercedes convertible and a Ferrari. He also had his girlfriend, Meegan, to keep him tethered to reality — or at least attempt to do so. In an interview with CNN back then, Rubin said they’d spend “a decent amount of quality time together … at least a couple hours during the weekend.” In 2009, then married with a three-year-old daughter, Rubin filmed an episode of Undercover Boss, epic-failing while trying to stack packages in a GSI warehouse and bonding with blue-collar employees. The most insightful scene was a brief glimpse into his private life — Meegan playing with Kylie in the background while Rubin scrolled on his phone. “He is definitely a workaholic,” Meegan said on camera. “Texting at three o’clock in the morning to Europe. He treats GSI as if it’s his baby.” Meegan tells me her exasperation wasn’t staged for television, and Rubin admits he isn’t a “zero to three” father: “Truth be told, I was not a baby guy. I connected with my daughter when she turned two and a half or three. If I had more kids, I wouldn’t be changing diapers. I could sit here and say I’m someone else, but I’m not.”

The couple separated in 2011, and Rubin dated cable news anchor and Rich Bitch author Nicole Lapin, reportedly only a month later. “It still makes me sad to this day,” Meegan says of their divorce. “We were going in separate directions. I was tired. I didn’t want the pressure — I’d already been so affected by people trying to get close to him for his money. I just have a different soul than he does.” Still, Meegan, an artist and a former Koresh company dancer who owns the Liberty Me Dance Center in Bryn Mawr, can’t say enough about her ex as a co-parent, businessman and human being. “He’s enjoying the fruits of his labor, as he should,” she says, adding, “Freedom is the foundation for happiness, and we both gave each other that gift.”

One of those fruits is owning a piece of the Sixers. (Rubin has also invested in Harris and Blitzer’s other teams, the New Jersey Devils and London’s Crystal Palace soccer club.) As Rubin tells it, his former neighbor, Ed Snider, approached him about buying the team after his eBay windfall, but Rubin passed without looking into it. “Josh and David are savvy,” he says. “They recognized the economics of the business were a lot better than I thought.” NBA commissioner David Stern recommended that Rubin get involved with Harris’s group, and soon the guy who’d made a mint with sports apparel was part of another elite group — pro team owners (and a ’Nova dropout among a group of Penn grads). Via email, Josh Harris calls Rubin “a great guy and a great friend … very creative, full of high energy.” His value to the team, Harris says, is “innovative thinking and his relationships.”

As for who’s responsible for the Sixers’ rise from paupers to playoff threat, Rubin insists that Harris and Blitzer make all the basketball decisions. Coincidence or not, the team has followed a playbook he’s most familiar with — suffering today in exchange for future success. “If you would’ve asked two years ago, when we were going through a really difficult time, people would say we’re a bunch of clowns,” he says. “Today, I think people would say we’re pretty smart, that we’re good owners, and you have to give that credit, first and foremost, to Josh and David. They’ve got the responsibility on their shoulders, and they chose to embark on a really long-term strategy.”

Asked about Rubin’s unusually close relationships with Embiid and Ben Simmons, Harris says it’s a benefit to the team: “I think it’s great to have a member of the ownership group who can relate particularly well to the players and be accessible for any questions or issues they may have. The old days of having a line of demarcation between the owners and players is long gone.” (Insert Colangelo Twitter joke here.)

Even longtime hater of the Process and Sixers ownership critic Howard Eskin doesn’t see a problem with Rubin mixing business and pleasure. “He loves being friends with the players, and I think it’s great,” says Eskin. “Why shouldn’t he enjoy his passion for the game? He doesn’t make decisions on those players. Maybe that’s a good thing.”

Now Rubin has his sights set on the toughest and richest club in all of sports — owners of NFL teams. His bid to buy the Carolina Panthers ended when the asking price ballooned from steep to insane (final sale price: $2.3 billion), but Rubin is “pot committed,” to use a gambling phrase he appreciates. “I believe I’ll have my chances to own an NFL team, and I’m excited to do it,” he says. But the thrill of being close to the action is nothing new to him; his first date with Meegan was, ironically, courtside Sixers seats, and he’s been friends with superstars like Julius Erving for decades. He’s made a fortune, literally. Aside from winning a championship, what’s left to do? “There’s a typical cadence when people are laser-focused on their business,” says Kopelman. “When they hit their 40s and 50s, they widen their aperture. They see their ability to give back.”

Meek Mill told his pal Michael Rubin about a dream he had while in prison: Rubin would fly to Chester, land his helicopter in the yard, and carry Mill away to freedom. On April 24th, the day Mill was released, Rubin was determined to make that vision real — even though it was after 3 p.m., the Sixers had a playoff game against the Miami Heat in a few hours, and there was no place to land at the jail. Rubin called in a favor from Harris, who owns the Harrah’s casino across the street, and secured permission to touch down there. “We pick him up, go to the game, and we’ve got multiple news helicopters following our helicopter,” Rubin says. “He’s in his jail outfit, he goes in, hugs everyone, shaves, takes a shower, goes out and rings the bell” — a new Sixers pregame crowd-hyping ritual. “It was insane.”

On the surface, this is another curious Rubin relationship, two guys with seemingly little in common. They met courtside at the 2015 NBA All-Star game in New York — Mill with then-girlfriend Nicki Minaj, Rubin with Kylie — and what began with his daughter chatting the stars up turned into Mill asking Rubin a barrage of questions about the Sixers, sports and business. “I felt like I met a different version of myself,” Rubin says. “I’m a sponge, and he was doing the same thing to me that I do to so many other people. I loved it.” Their shared curiosity led to a fast friendship; Rubin estimates Mill has joined him on 50 separate trips across the country and beyond.

There’s chatter in some circles that the bond between the rich white guy and the ascending rap star is really little more than a branding opportunity, perfect for Rubin’s new celebrity-adjacent public image. But a story Rubin tells about Mill’s case suggests that their connection and his passion for Mill’s cause run deep. “If he wasn’t my boy, I would have never cared,” Rubin says. “I don’t want to seem like some great guy. If Joel said this happened to his friend, I would have written a check. Because it was my close friend, it’s as personal as it gets.” Mill and Rubin had a long-running argument, with the rapper insisting there were two Americas — a black one and a white one — and Rubin saying give me a break, you have a great life, there’s one America.

Mill went to jail in November for violating parole on much-debated gun and drugs convictions from 10 years ago. Rubin was in the courtroom that day, as confident that Mill would be let off as he’s been about any business deal he’s made.

“Michael,” Mill said through the phone from prison hours later, “this is what happens to black people.”

“You’re right, I was wrong,” Rubin said. “I will get you out of this.”

Mill’s incarceration lit a fire under Rubin that his friends say consumed him unlike anything they’ve seen outside his business and his family. Rather than sit idle as the wheels of justice creaked slowly, Rubin took the case to the court of public opinion, launching the Free Meek campaign on billboards and with hashtags with the help of luminaries including Dr. J, Kevin Hart, Allen Iverson and Jay-Z, head of Mill’s record label. (Sources say that between legal fees and other costs, Rubin and Jay-Z split more than $5 million in expenses on Mill’s behalf.) The Inquirer revealed that Ed Rendell personally called Common Pleas Court Judge Genece Brinkley to encourage a compromise on Mill’s parole restrictions. Rubin brought Mill’s case to Rendell’s attention, but he says he didn’t ask him to make that call. Still, he apologizes for none of his aggressive tactics, including his attacks on Brinkley. “My whole life, I evaluate people. I evaluated her, and she was psychologically crazy,” he says. “I wasn’t backing down to her or her broken system. I think a year from now, she won’t be a judge. I think she belongs somewhere between unemployed and being in jail.”

Rubin is applying his appetite for risk and long view in business and sports to the cause of criminal justice reform — not just here, but across the country. He’s announced he’s in the process of setting up a foundation to help people like his buddy, folks living in the other America he never knew existed despite his close proximity to athletes who surely knew otherwise. His goal: to bring “business sense” to a broken system, tackling everything from parole and bail reform and offender reentry to mass incarceration that disproportionately impacts minorities. Rubin won’t confirm who’s involved yet, but the coalition he’s building will be backed by deep pockets and A-list power, and Rubin is dedicating more than $10 million of his own money to the cause. Local political rising star Omar Woodard, director of the venture capital GreenLight Fund that Rubin has backed, says Rubin is uniquely positioned to turn what looks like a quixotic crusade into a victory. “This could change the lives of millions of people,” he says. “This is long-standing work. There’s going to be wins and losses. Who knows that better than entrepreneurs? The fact that he’s found a passion with this, I’m thrilled.”

Someone else who believes in Rubin’s world-shaping potential — and impacts his life like few others — is Robert Kraft. When Kraft’s wife died from ovarian cancer in 2011, Rubin could relate — he struggled after losing his father to heart disease. “I was devastated for a year,” Kraft says. “My kids thought I was not long for the world. Two people helped me a lot — a young lady who I still see a lot [38-year-old model/actress Ricki Noel Lander], and developing a relationship with Michael in both a personal and professional space. We’re both a little nuts — in a healthy way.”

Kraft somehow connects all of the dots of Rubin’s story at this moment in time. Both are considered kids at heart: For Kraft’s birthday in June, Rubin posted a photo of Kraft’s head on Pats tight end Rob Gronkowski’s ripped body; Kraft, in a backward Pats cap, posed for a Monte Carlo pic with Rubin and a tray full of hangover remedies. They bonded over grief for the loved ones they missed. They’re also time-shifted mirror images of each other — Rubin a younger version of Kraft, and Kraft a beacon on the far-off horizon, a life well lived with no signs of slowing down (and a hand with five Super Bowl rings).

Kraft was so taken by Rubin’s passion for Mill’s case that after the two men vacationed in Turks and Caicos with their girlfriends, he joined Rubin for a jailhouse visit in Chester. “I wasn’t really into rappers, but my girlfriend liked rap and exposed me to Rick Ross, and we had him perform at one of our after-parties at the Super Bowl,” Kraft says. “I realized that there’s a lot of messaging there that has a lot of depth and speaks to what’s going on in the inner city. … I told Meek, you have to have boundaries and be careful who’s around you. You can’t disappoint these kids who look up to you. He’s really intelligent and a good guy. That conversation really bonded us.” Kraft’s connection to Rubin is on another level: “He’s a very special person. He’s like a brother. He’s helped me be more open-minded about things. He’s very good at selling, but he has empathy.”

Rubin delivers his sales pitch regarding Mill’s future with conviction. He’s certain Mill has seen the last of prison, despite a setback in August as the Pennsylvania Supreme Court denied a motion to remove Brinkley from the case. But when I ask about a nuclear option I heard he’s pursued — asking Governor Tom Wolf, a vocal Mill supporter, to recommend a pardon if Mill loses all appeals — Rubin pauses before speaking: “It’s never going to come to that, in my mind.” That rare hesitation suggests less a lack of confidence than a sign that Rubin’s already thinking ahead to his next moves.

Before we land in Foxborough about two hours ahead of the Birds-and-Patriots kickoff, Rubin finds a way to turn a Mill visitation story into Joel Embiid’s humiliation. When Kevin Hart joined Rubin at the state prison, they walked through crowds of inmates as the comedian shook hands and dapped with the starstruck convicts. For Embiid’s visit, they met Mill in a private room and made no contact with the prisoners. Still, says Rubin, “I’ve never seen someone more terrified in my life.”

“I was scared,” says Embiid, who’d never been to a jail before. “I was literally shaking.”

“Just to put this in perspective, Joel literally turned white as a ghost,” Rubin says. “Kevin Hart, who’s all of five-foot-two, was completely comfortable.” Months later, when Embiid learned Mill was about to be a free man, he FaceTimed Rubin as he jumped up and down on his bed: “I thought he was never coming out,” Embiid says.

When the subject changes to the upcoming Sixers season, Embiid flexes his usual confidence. “We definitely have to make it to the finals — that’s the first step,” he says. “Everybody’s getting better. I’ve gotten so much better. Markelle [Fultz], I’ve seen the videos, he’s got his shot back. Everybody looks good. … We felt like we could have beaten Boston, but every game was close. We just couldn’t finish. Next year is going to be even better.”

Rubin agrees but can’t resist another joke at Embiid’s expense: “He’s not going to be soft like he is in the off-season, when he’s in love and can’t focus.”

“I actually think being in love helps you focus,” Embiid says, deadpanning again. “It’s motivating.”

After 90 minutes, the Rubin/Embiid comedy show ends as the pair and their business pals hop off the heli and into a waiting golf cart that whisks them off to say hi to Lurie and hang with Kraft. The billionaire who horses around like a teenager is a bundle of contradictions: genius and dropout, family man and party boy, team owner and posse member. Framed that way, Rubin might seem like a long shot to own a team in the notoriously conservative NFL, and his chances to change America’s criminal justice system might appear even slimmer. But Kopelman’s analysis of Rubin’s bold predictions for his business could well apply to all of his endeavors. “He’s playing the long-term gratification game,” he says. “If you’re asking if I’d bet on Michael Rubin, I would.”

Published as “Michael Rubin Is Playing the Long Game” in the October 2018 issue of Philadelphia magazine.