Michael Rubin and Lil Baby first met in the Bahamas. The CEO and the rapper found themselves, in January 2021, sitting around the same baccarat table with their mutual friends Drake and Meek Mill. Baby had begun making music a few years earlier after serving two years related to drug and weapon charges in Atlanta. Now, like the two other rappers placing their bets, he was beginning to mix with billionaire businessmen.
“We ain’t win,” Baby recently recalled. “We had a great night, though.”
As with Drake and Meek, Rubin, 51, struck up a friendship with the 28-year-old rapper. Each of the three has recorded lyrics about him, but Baby put it the most bluntly on a 2022 song: “I get my advice from Mike Rubin.”
“He’s got the best story ever,” Rubin said, sitting nearby. “Because this guy didn’t even rap until he got out of prison, and it shows you, you can do anything at any time in your life.”
They were in a Sprinter van on a Tuesday morning in June, heading from a Harlem school to get to Rubin’s company jet at LaGuardia. Fanatics, the sports merchandise business (jerseys, cards, more) that Rubin has run since 2011, was holding its inaugural Merch Madness event. In cities including Los Angeles, Miami, and Dallas, a wealth of athletes and musicians including Donovan Mitchell, DJ Khaled, Quavo, and Chris Paul—most of them personal friends of Rubin’s—gave out licensed apparel to local kids and families in need. It was an instance of the philanthropic bent Rubin has demonstrated in recent years as well as of the eye-popping and mildly befuddling constellation of personalities he has assembled around himself over the same period.
Rubin and Baby boarded the plane. Rubin picked up the phone—Major League Baseball commissioner Rob Manfred was calling to ask how he could get involved in the charity event. “You know, we did that in 30 cities,” Rubin said to no one in particular on the 10-seat jet. “Next year we’re gonna do it even bigger.” The day’s itinerary had Rubin traveling to Massachusetts, where his close friend, New England Patriots owner Robert Kraft, played host for a Merch Madness event, and then on to Philadelphia, where the 76ers, which Rubin partly owned until selling his stake last year, hosted another. As his group navigated a series of helicopter rides, Rubin talked in quick bursts, twitching with enthusiasm over the time they were making and how the weather was holding up.
“I really feel like I’ve had a profound effect on rappers’ timeliness,” Rubin reflected.
“Where we going now?” Baby asked in the van.
A pair of videographers and a photographer tagged along—Baby would later release a song about the event and a music video that pulled from the footage—and Rubin’s 17-year-old daughter, Kylie, rested her head against the van window. Rubin regaled Baby, engaged and occasionally puffing from a sour apple vape, with business tales. “It’s cool to be an entrepreneur,” Rubin said. “It was almost nerdy to be an entrepreneur when I was a kid.”
Rubin had come to see Baby as a brother in the years since they met. “I always say,” he noted, “if I grew up how he grew up, I would have been the biggest drug dealer on the planet.”
And if Baby grew up like him, they reasoned, he’d be a full-fledged businessman. “By the way,” Rubin said, “I still expect you to be.”
In 1998, Diddy, then at his Puff Daddy zenith, threw his first White Party in East Hampton. “??I had the craziest mix,” he told Oprah in 2006. “Some of my boys from Harlem; Leonardo DiCaprio, after he’d just finished Titanic. I had socialites there and relatives from down South.” It registered as a capsule of the era—Paris Hilton, Kim Kardashian, Al Sharpton, and Salman Rushdie would attend in the years to come—and an emblem of hip-hop’s cultural weight. The commingling of rappers, the business class, and the social set was a novel phenomenon, and Diddy’s party distilled it into an event that Manhattan media could obsess over in its own backyard. “The people in the Hamptons thought the first party was the end of the world,” Steven Gaines, the author of Philistines at the Hedgerow: Passion and Property in the Hamptons, said in The Hollywood Reporter’s 20th anniversary commemoration of the party. A decade later, with hip-hop long the dominant force in American culture, Diddy retired the event with one last bash in Los Angeles in 2009.
There have since been many parties with a similar dress code, but to pick up where Diddy left off, a host would need the credibility across celebrity spaces, the ambition, and the money. Today, there’s Rubin, who bought his $50 million Bridgehampton home in 2020 and started to host his own White Party—not so much an intrusion into the Hamptons as the crown jewel in a growing social empire. The divisions of fame that Diddy had a hand in flattening have now mostly converged, at least at a certain stratum of wealth. Jay-Z hangs out with Jack Dorsey and sits on the board of his company Block; Dorsey donates to Jay and Rubin’s criminal justice reform group; Jay and his entertainment company produce the Super Bowl halftime show; and Rubin throws the party he attends the day before. The high-end pieces of sports, business, and music have been sitting in close proximity, and Rubin has become relentless about putting them together.
“Obviously, I’m working 24/7 most days,” Rubin said on the jet, but the Fourth of July was approaching. “I’m gonna have a party at my house with a good group of people. And I’ll go from 5 p.m. to 5 or 6 a.m. And we’ll be like kids, we’ll just have a great time.” Eager, boisterous, and prone to backslaps and fits of free association, he wore his CEO impresario role lightly.
“Are you mentally prepared?” he asked Baby. “Double or nothing on last year’s bet?” If Rubin fell asleep first, Baby would shave his head; if it was Baby, Rubin would snip three of his braids.
The party has quickly picked up an aura as the sort of venue, exceedingly rare in the smartphone era, in which Rubin’s famous pals can truly throw caution to the wind. The year before, his girlfriend, 32-year-old model Camille Fishel, with whom he has two young children, fell off a stage (Drake, Travis Scott, Diplo, and more performed) and ended up in a neck brace at the hospital. Rubin recalled more of the party’s gentle debauchery. “Which D’Amelio sliced her finger?” he asked Baby, Kylie, and a few Fanatics employees on hand. (Kylie’s mother, Meegan, and Rubin divorced in 2012.)
“I keep that thing so authentic,” Rubin said. “We don’t commercialize it at all.”
The third go-around of the event in July crystallized Rubin’s standing as a connector while also reaching a new level of saturation. If the hip-hop and sports worlds had long been aware of Rubin, this year’s event saw more coverage in the general gossip press of TMZ and the Daily Mail. Kardashian and DiCaprio made the jump between White Parties. Jay-Z drove his longtime friend Tyran “Ty Ty” Smith, Corey Gamble (boyfriend of Kris Jenner), and the Israeli investor Vivi Nevo over in a Land Rover to meet Beyoncé, whose mother, Tina Knowles, arrived with Kelly Rowland. Ben Affleck and Jennifer Lopez arrived with Violet, Affleck’s daughter with Jennifer Garner. Adam Weitsman, the upstate New York scrap metal magnate, posed with the Chicago drill rapper Lil Durk. In turn, Rubin’s gathering became one of the gaudiest and most heavily dissected celebrity spectacles in recent memory, or as he put it in an Instagram supercut he posted the next day, “a literal movie.”
Much of the ensuing tabloid coverage circled a basic question: Who is Michael Rubin? “It was game on with Tom Brady and model Emily Ratajkowski—NOT Kim Kardashian” at the party, the Daily Mail reported, kicking off a new rumor cycle while throwing cold water on its last. (Kardashian was indeed there and used her appearance as a mini content cycle of her own, recounting that she drank 11 shots.) ESPN’s Stephen A. Smith chided Rubin on his podcast for not inviting him. 50 Cent, echoing one swath of social media reaction, criticized Baby for a photograph in which he grinned widely as Rubin hugged him around the neck with seeming force.
“Can’t believe Puff let a white brother take July 4 Hamptons white [party] away from him,” the veteran hip-hop journalist Elliott Wilson wrote on Twitter.
The following week, Rubin sat in his office at Fanatics’ Manhattan headquarters and pondered the party’s successes. “The White Party, pretty well-run, to be honest,” he said. “There’s always little tweaks. I’d say we got more of that right than wrong.” A few days later, he and Fanatics held a party with the National Basketball Players Association in Las Vegas. It was fatiguing, he said, but necessary—“just going to touch all the people that are important to us.”
Rubin and his Fanatics lieutenants are fond of mentioning the 1.87 GPA he had at Villanova before he dropped out after a semester to focus on business. He professed to compensate socially. “Let me ask you a question,” he said. “Of most wealthy people, I’m talking people that are worth many billions, what percent do you think are fun?”
“I think one. They’re mostly painfully boring. They’re the most stiff, they can’t speak, they’re boring as shit. And by the way, most are old too. I’m relatively young and relatively fun. So I think it’s a unique setup.”
He was proud of his business, his relationships, and, he emphasized a few times, his appetite for indulgence. “I’m a maniac when I’m drunk,” he offered, recalling how Kraft once FaceTimed him at 10:30 a.m. “I was still in the casino with James Harden and Baby.”
Curled up on a couch with his sneakers tucked under him, Rubin, wearing shorts and a Louis Vuitton polo, held a more measured pose than when he was flying around the Northeast the month prior. Looking back on the last few years, “Fanatics got bigger, I got more well-known,” he said. “I think that’s generally good for the business.” The night before, he had been at the opening of Jay-Z’s Brooklyn Public Library retrospective, and in a few hours, he’d head to the 20th anniversary gala for the rapper-mogul’s education foundation.
Rubin grew up in a middle-class family in a largely white suburb of Philadelphia. “I was always selling stuff,” he said. At 14, it was used skis; then liquidated goods; then an e-commerce company, GSI Commerce, that he founded when he was 26 and that eBay bought for $2.4 billion in 2011. Fanatics was then a subset of GSI and he bought it back from eBay to continue his ongoing expansion into sports, turning the operation into one that depended on the company’s relationships and licensing deals with the major sports leagues. Last year, he sold his minority stakes in the 76ers and New Jersey Devils to avoid a conflict of interest when Fanatics got into the sports gambling business.
The move came with some strife. Earlier this year, Fanatics offered the sports gambling operation PointsBet $150 million for its US business. Jason Robins, CEO of sports book rival DraftKings, announced a $195 million offer in response, which Rubin described at the time as a “desperate” attempt to slow Fanatics down. Rubin said he had been a friend to Robins, who once stayed at his house. He raised his offer by $75 million and proceeded with the acquisition. “They just decided they wanted to be disruptive to us,” he said. “That’s a guy who wants to compete but he’s got the EQ of a gnat.” (“Michael is someone Jason considers a friend,” DraftKings said in a statement. “DraftKings’ proposal to acquire PointsBet was solely a business decision that we felt was in the best interest of our company and shareholders at the time.”)
“One thing I’ve learned,” Rubin added, “is the bigger we get, the more people you have conspiring behind your back.”
In 2015, Rubin met Meek Mill. As each has often recalled, they were sitting courtside at the NBA All-Star Game. Meek was dating Nicki Minaj at the time, and Kylie, then eight, was a fan of hers and approached. Meek and Rubin started talking too; neither knew who the other was, but they were from different parts of the Philadelphia area and stayed in touch. “My life was a lot simpler then,” Rubin said. “We were hanging a lot, having fun together.”
Meek, then 27, had been on probation since he was a teenager, stemming from drug and gun charges. (The conviction was eventually overturned.) He had been trying to tell Rubin about the unfairness and precarity of his situation, but by Rubin’s account, “it just went in one ear and out the other.” In 2017, Meek brought Rubin to a hearing about a pair of his recent parole violations, and Rubin was stunned to watch a judge sentence his friend to prison. “That was the most out of control I’ve ever felt in my life,” he said, “because here I am as this relatively successful businessperson in the state that I grew up in, watching them put someone in jail for two to four years for not committing a crime.”
The case quickly became a go-to reference point in the national conversation around mass incarceration and prison reform. “Free Meek” was a rallying cry, and Rubin publicly campaigned on his behalf. “What’s happening to Meek Mill is just one example of how our criminal justice system entraps and harasses hundreds of thousands of black people every day,” Jay-Z, who had signed Meek to a management deal through Roc Nation, wrote in a New York Times op-ed. When Meek was released the following year, Rubin picked him up in a helicopter and brought him straight to a 76ers playoff game. The circumstances of this homecoming were widely publicized, and after Meek and Rubin reunited, they joined with Jay-Z and Kraft to create Reform Alliance, an advocacy organization focused on changing probation and parole laws.
The group wasn’t alone in an escalating celebrity sector of the movement. Rubin began working with Kardashian, who started studying law and met with then president Donald Trump concerning the case of Alice Marie Johnson. (In 1997, Johnson was sentenced to life in prison on drug and money-laundering charges. Trump pardoned her.)
As Rubin’s company and his activism grew, so did his visibility. Along with Jay-Z, Meek, and others, he gave Kraft a Bentley for his 80th birthday in 2021. He had been a friend to athletes, to musicians, and now to a more general class of celebrity. Criminal-justice issues had become a constant in his life—“I’m, like, maniacally focused”—but he has more recently noticed the winds shifting once more.
“The pendulum has swung back and forth,” Rubin said. “Think about it. No one cared about the issue when we started, then everyone cared about it when George Floyd happened. No one cares about it again.”
As Rubin and Baby arrived in Philadelphia in June, they stepped aside for a rapt-looking conversation with 76ers center Joel Embiid. Rubin, Embiid later said, stood apart from the other sports business figures he’d come into contact with over his career. “He’s willing to listen, he understands, and he’s not afraid of controversy,” he said. “And he’s a hard worker, that’s the main thing. This dude don’t stop.”
Gary Vaynerchuk, the advertising guru and irrepressible internet personality, a friend of Rubin’s with his own rap-heavy Rolodex, defined himself and Rubin as “purebred” entrepreneurs—“what I mean by that is you live and breathe it.”
“I think the reason both of us have found relationships in those genres is they are the other humans on earth that are closest to you,” Vaynerchuk said. “In sports and music, you can’t hide. Either there’s 100 trillion downloads of your song or there’s not. Either you scored 42 points or you didn’t.”
Though he’s keen on forging business partnerships with his friends, Rubin described a more emotional approach too. When he, Embiid, Baby, and Meek recently flew to Las Vegas together, they discussed how they communicate with one another. Embiid told Rubin he didn’t say “love you” growing up. “But Joel says to me, love you,” Rubin said. “I say to Joel, love you. I say to Meek, love you. I say to Baby, love you.”
He grew more animated—extrapolating a few steps from the exchange he was describing. “What the fuck do you mean we don’t hug in our culture? I hug 6,000 people a day. Every day, you see me, someone comes in, I give him a hug.”
Plenty of middle-aged white men, I proposed to Rubin, would love to be friends with famous, talented young Black men. Before he and Vaynerchuk, there was Trump, who partied with rappers in Manhattan in the ’90s, served as lyrical inspiration for more as the years went on, and pardoned Lil Wayne and commuted Kodak Black’s sentence in 2021 after hosting Kanye West in the Oval Office.
“First of all, I don’t feel middle-aged,” Rubin said. And anyway, he pointed out, he has a more general agenda and cohort. The next day, he had a walk scheduled with Kraft at 7 a.m., where they’d discuss the Sun Valley conference Kraft had just attended, and he had already talked to Brady four times that day.
When I called Meek to hear his rendition of Rubin’s foundational friendship, he spoke for 10 minutes without being asked much of a question.
“Mike made a vow to me just as a friend,” Meek remembered. “I’m not gonna leave you in here by yourself.”
He seemed sensitive to the idea that Rubin had only recently come to the place he’s in: “Everybody wondering where Rubin came from, he just popped up on the scene to be around.” But Meek pointed to business opportunities Rubin had steered him toward, as well as the duration of their relationship. In 2016, he was on house arrest, and “Mike was in the house, just him and my whole Black family before any of this stuff took place. And now he getting caught up in narratives, people be like, where’d Mike come from? Yo, Mike is just a young hustler who started a ski business early in Pennsylvania and turnt it up.”
Leaving Philadelphia, Rubin and Baby hopped in an SUV and headed for the helicopter back to New York, returning a missed FaceTime call from La La Anthony on the way. Baby had recently stayed in Rubin’s West Village penthouse. “Let’s do dinner one night this week,” Rubin suggested.
Earlier in the day, he had recounted one of his first entrepreneurial conquests for Baby. “Crazy story,” he said. “I don’t know if you’ve ever heard this before.” At 14, while operating his ski shop in the summertime, Rubin said he bought 40,000 pounds of ice cubes to make a slope in the parking lot. The novelty attracted press, but it would have been easier, he figured, if he had the tools of social media at his disposal.
Baby listened intently and a little wistfully. “Maybe you could have been 100 times more successful,” he said. “Maybe a million times.”