It’s almost too on the nose, like a taste of Aubrey Graham Champagne poetry. At 5 a.m. in Toronto, a black car swoops by my hotel and delivers me to the OVO Athletic Centre, the Drake-blessed practice facility of the Toronto Raptors. It’s the first day of the Raptors season, and Masai Ujiri, the team’s president of basketball operations, is starting the day the way he always does: with a workout. Under a glowing neon owl, his assistant, Tim, greets me with an energetic buzz. “This is actually how he is,” Tim says. “The early morning workouts are a thing.” We walk onto the practice floor, where Masai is sweating hard with a member of the team’s training staff.
Masai is carrying two large orange Home Depot buckets around the perimeter of two side-by-side courts, while Ray Chow, a trainer who’s worked for the Raptors since 1996, follows him. When he rests between laps, I open the buckets to find dumbbells inside. Masai, now kickboxing, chuckles at my discovery. Then he carries two weighted baseball bats, upright, down that same length of the floor. Then, curling shoulder presses with a weighted, scythe-like object Ray calls an “omega.” Why is arguably the most brilliant mind in the NBA doing hourlong, Bane-style workouts before the crack of dawn? “I need that energy in the morning, man!” he says.
That energy, along with a hefty dose of negotiating savvy, has paid off. It’s made Masai the consensus best front-office executive in basketball—the kind of guy other teams are afraid to trade with, because he regularly winds up on the winning side. No wonder, every now and again, speculation circulates about Masai fleeing Toronto to save moribund franchises from Washington to New York to even Europe. It’s what led him to put all his chips on a risky 2018 deal for Kawhi Leonard, who at the time had just one year left on his contract and was in uncertain physical condition. (Along with Masai’s carefully assembled team, Kawhi delivered a championship before jetting off to join the Clippers in L.A.) It’s what’s made him coveted by sports organizations all over the world. It’s the same energy he applies to expanding basketball on the African continent, and to advocating for racial justice, which became a more personal issue after a courtside encounter with a cop, in the moments immediately following that championship. It’s what’s made him that extremely rare entity: a sports executive who’s almost as famous up north as his players are worldwide.
He enjoys perhaps the greatest job security in the NBA, but maintains a spartan existence. Masai doesn’t drink coffee. Tim says he’s seen him have a cup only twice in four years. In college, Masai was routinely the designated driver for his friends, and to this day doesn’t drink at all. He even fasts with Ray during the season, sometimes for up to a week, to “make their mental strength stronger,” Tim says. He barely watches the Raptors in public, opting for a burgundy couch in the arena’s basement with the video crew. He spent road games during the Raptors’ championship run bent over in the parking lot at Oracle Arena, squinting at the feed of the game on his phone.
“Sometimes I don’t want to be bothered by anyone or anything,” he tells me. “I can never go out in the crowd,” he continues. “It would be a riot.”
That much will become obvious over the rest of our time together. “He’s certainly revered,” Nick Nurse, Toronto’s head coach, tells me. “The persona he exudes, the class that he shows, the things he’s accomplished, they were meaningful. People respect and admire that in a big way up here.”
That last part is hard to miss. Women around the facility cuss in surprise when he randomly pops up around the building. “Oh, shit, it’s Masai Ujiri,” one woman says, as if he’s Canada’s version of Idris Elba. Construction workers urge him to consider executive office. “You should run for prime minister!” one hollers as we get into an elevator. He greets it all with knowing glances and half smiles. “If I come out and speak or say something,” he tells me, “it’s for a reason.” Behind the hushed facade, he’s still hungry to create a consistent NBA champion north of the border.
“The competitive part of him is misunderstood,” his friend the ex-coach and current TrueHoop writer David Thorpe tells me. “People see him as pensive, thoughtful, always smiling. But when he cursed about playing Brooklyn? That’s Masai. The other stuff is just window dressing. I’m not saying he’s faking it; that’s just part of his personality too.” Thorpe says that Masai isn’t happy making a bunch of money and being successful. “You see a really big picture, a man trying to hit that grand slam and not just keep knocking out singles and surviving,” he says. “That’s a really important thing: Masai has that juice of, ‘I wanna kill everybody.’ He is not content with just winning one title. In fact, I think not having Kawhi has juiced him up even more.”
And Masai doesn’t just have outsize ambitions about where his team should go. He has big thoughts about what’s possible for entire organizations, for whole continents, and for the future of basketball itself.
“I still feel like Toronto is a gold mine,” he says. “There’s so much potential in the ball club, in the ability to be the only team outside the United States where you can be the center of the globe, that sees it from every different perspective...and you don’t have to fight against the other teams. You can build what you want to build and have an incredible identity in many different directions. I saw the potential for building that here. Because you must be proud of who you are.
“You have to show more passion than ambition,” he continues. “Yes, we all want to be ambitious, but passion will lead you to incredible places. This is where the game finds me today, and I will serve it with every last breath in my body, with all the blood in my body. I believe in the game that much.”
When he was a boy in Zaria, Nigeria, Masai Ujiri dreamed of basketball. But education was king to his parents. Why couldn’t he be in medicine, like his nursing educator father or his doctor mother? Beyond that, he met a traditional Nigerian roadblock. “When you come out of your mother’s womb, it’s soccer in Africa,” he says. That sport kept his interest until he was 11 or 12. But once he got to primary school, basketball found him. His walk to school took him past a basketball court, where he’d stop to shoot with a soccer ball. “I fell in love with the game. I was more talented in soccer, but the game of basketball,” he says, gripping an invisible rock in his palms, “it just blew me away.”
His parents started to sense they were losing the battle with their son, but thought they might win him back by overloading him. His mother would bring home VHS tapes of old movies, like Come Fly With Me and The Fish That Saved Pittsburgh; she’d buy copies of Basketball Digest and Sports Illustrated; she tracked down grainy, months-old footage of Hakeem Olajuwon, Moses Malone, and Ralph Sampson. Of course, it backfired: He was enthralled with the foreign delights. “Watching it on those VHS tapes or reading in those magazines, it became part of us,” he says. Basketball put him in a trance.
It quickly became his life. He went to college in Montana, and then spent his 20s playing professionally in England, Belgium, Finland, and Denmark. Mom and Dad worried he was gallivanting across the world. Even he knew his pursuit was getting mindless. “I wouldn’t even consider what I was playing professional basketball,” he says.
But all that aimless hooping did impact the way he thought about societies—how they were built, and how we should act in the ones that aren’t our own. He was itinerant, and he wondered: How do you make a lasting community? Though the money wasn’t that good and the leagues were barely recognized, he found perspective. “Instead of being a coach, I saw myself more as the person who puts the team together,” he says. Masai always had a sense that basketball would be the thing he could use to effect change—maybe in Zaria, maybe in the world. “For some reason, there’s this path that basketball has created for me,” he says. The sport helped him understand the world around him, and gave him a life to cling to. “There’s just something about basketball that kept me going. I didn’t know it was this, but I knew that I wanted to be part of this game in a special way.”
Eventually, he gave up on playing basketball and started trying to work in basketball: He drove draft prospects to NBA workouts in 2002; he coached the junior Nigerian national team; he impressed coaches and personnel directors with the Orlando Magic, an organization with Black folks in the head coaching role (Doc Rivers) and front office (Gary Brokaw) at the time. By the end of the summer, he got the general manager’s number and, he says, “I called John Gabriel every day for the next six months, until he actually took the call.”
Masai became the Magic’s new unpaid international scout, surviving on money he’d made hooping in Europe. That was fine with him. “I had that NBA pass that said ‘Masai Ujiri, Orlando Magic’—the golden ticket that could get you into those gyms,” he says.
The next year was spent sleeping on cold floors in Belgrade and rapidly depleting his savings. He’d head to Denver a year later, where, he says, the Nuggets offered him a princely $40,000 salary. To this day, he says, Orlando claims they didn’t have enough money to keep him. In 2008, he came to Toronto as the director of global scouting for the Raptors, working under longtime exec Bryan Colangelo. He learned at Colangelo’s side, and eventually the Nuggets brought him back, this time as the first African general manager in a major American sport.
Finally, his mother could stop worrying. “I always had a warning when I was doing something wrong,” he says. “If I wasn’t doing so well in school, or if I was playing basketball too much as a child, Mom would say, ‘Is that basketball going to feed you? Is that basketball going to feed you?’” Here comes that knowing chuckle. “Well, you know,” he offers, “now it’s feeding a lot of people.”
Two decades ago, Masai was, by his own admission, a third-rate player still pretending to be a basketball lifer. Now, late in the morning in his glass office overlooking Toronto, he shows off a little bit of what comes with becoming a country’s standard-bearer. “That’s my boy, yo,” he says, pointing at one of the four photos he has with Barack Obama. He leans back in his chair, his singsong accent shining through like the background vocals of a Fela Kuti jam. “This was years ago,” he says, pointing to one picture. “He was in Denver; he came to campaign before his reelection. He came into town, and he had that bad debate with [Mitt] Romney. I was there. I was supposed to see him after that, but he was so pissed and he flew out.”
Denver did a lot for Masai. Sure, the team made him the league’s only African general manager, but also one of its lowest-paid. But Masai didn’t miss the opportunity. “That was my foot in. Who am I to stand asking for money?” he says. “This is a position you dream about getting. What are we going to do? Fight over this?”
And outside of the money, he’d been dealt a tough hand in his first few days on the job: Carmelo Anthony, the best player in franchise history, was publicly demanding a trade to go home to New York and play for the Knicks. In theory, Masai’s leverage was reduced because the whole world knew Melo not only wanted out, but likely had a single destination in mind. Yet, after a protracted negotiating period, he came away with one of the great hauls in modern NBA history.
In working out an intractable situation, he began to put together a philosophy of dealmaking and team-building that’s made him among the best in the world at what he does. “Deals are very hard to make in the NBA,” he says. “Trading a player with one year left on his contract—he’s not sure in his head what he wants to do; other teams are saying that they don’t want to give up a lot of assets for him coming to their team for one year. You are battling all of those things. Then you’re battling the chemistry of your team.... All of these things around the trade made it tough.”
Masai’s general approach is rooted in his time abroad. “It exposed me a lot,” he says. “It helped me know the game was going to get global. And once it does, there are going to be players all over the world.” That experience made him see basketball more strategically. “You grow up out there. You’re out there on your own. There’s so many things you have to figure out: There’s language, cultures, different styles of play, learning how it all translates to the game over here. And you learn to judge specific types of talent.” It’s easy to assume Masai had a baked-in advantage for the NBA’s era of drafting international players. But just being there before everyone else isn’t always enough. “It’s not easy, you know,” Masai says. “There’s almost no right or wrong [out there]. You just have to figure it out.”
Agents speak of Masai as if he were a family member. “He makes it feel like I’m talking to an old friend,” says three-time NBA champ turned Wasserman agent B. J. Armstrong, “whether you are in a negotiation or just talking about life or visiting him at a game.” Armstrong says he once told Masai he was passing through town and would say hello if Masai wasn’t busy. “I didn’t expect him to call me and say he was leaving me two tickets, front row, a parking pass, and would make sure someone came and got me at halftime to bring me to wherever he’s at to make sure we say hello. And then,” Armstrong says, almost guffawing, “he asked me if I needed a ride or anything to the game! Like, I didn’t ask for any of that. Who goes out of their way to do that?”
In a business of around-the-clock scouting and player monitoring, plus development and backdoor dealmaking, genuineness—or at least a forthcoming attitude—can make a world of difference. “That’s something people recognize: All you really have is your reputation. Business is a long time, so people remember how they’re treated,” Ernest “Kiki” VanDeWeghe, the Nuggets’ former general manager, tells me. Whether you win a deal or not, folks know what happened in the room. One of the things VanDeWeghe tried to impress upon Masai, he says, was to always consider who’s on the other side of the table.
“One thing we always tried to do in Denver, and I think Masai tries to do this as well, is, before you go, try and make a deal with somebody: You always think about what they need, and if you were sitting in their shoes, what would you be looking for?” he says. “Not everybody approaches a deal like that. Even though he’s trying to make the best deal for his team, he also recognizes you’re going to deal with agents and team executives again. If you treat them well and think about how you can help them accomplish their goals as well…it’s an approach that resonates with people.”
Thorpe says that Masai “knows everybody and has no enemies.” He thinks of him as a “super connector,” endlessly building out “Masai’s Sphere of Influence.” “It was important who he knew on the inside: what assistant coaches, the seven-footer everyone loves that’s really lazy, or the guy that got hurt when he was 17 but could be really good when he’s 20. Inside information is really valuable,” he says. And Masai learned early on, he says, how to wield it as currency. Thorpe says that when Masai was a lower-level executive with the Nuggets, he maintained a home in Phoenix. Thorpe was training several NBA players, and “there was a club in Phoenix a lot of the players would always love to go to. It was a place I did not want my guys to go to the night before a game. So I called Masai,” who said that “of course” he went to that club, because that’s where players went. “Never once did he say one of my players was there, but that doesn’t mean he was telling the truth,” Thorpe says, laughing. “He was also probably loyal to his guys.”
The key to Masai’s success is not just that he can find prospects no one else is looking for, Thorpe says. It’s his ability to build a winning culture. “Look at the Sacramento Kings: You can’t tell me they’ve just picked bad players, because they haven’t. They just have no idea what they’re doing with the talent; they don’t know how to build the culture, pick the right coaches, or do the right player development. They have failed and failed and failed,” Thorpe says. “But Masai can take a player, and if that same player was taken by the Kings, they wouldn’t be the same player they are now, on the Raptors. That’s where his sphere of influence has been the most profound.”
The big thing Masai learned from Colangelo, before he got the Denver job, was how well you have to work the margins and the details that can separate you from your competition. “He knew everything in the building,” Masai says of Colangelo. “Some people criticize that he was too passionate or detailed, but to me, that’s an excellent character trait to have.” Masai found a man who breathed the same air he did. “He lived, dreamed, ate basketball.”
Which meant what was happening in Denver was something he was prepared for. It took months, but Masai never sweated. He sent Melo to New York, and the Nuggets, using the bounty Masai had secured, sprinted to the playoffs and instantly became a consistent contender. In 2013, he was named Executive of the Year, the only non-American ever to achieve that, and the third Black person to do so this century.
Yet none of that really made an impact.
“To be honest,” he says, looking away from me and toward the ceiling. “I was still in it. I was chasing a championship. I didn’t even see at the time that I won Executive of the Year or all the records. All that came to my mind was: How do you do it again? How do you go forward? How do you win? How do you continue to excel? How do you evolve?... At that time, what I did, that’s not success.” He takes on a condescending, self-deprecating tone. I cannot tell if this is Masai Ujiri or his mother criticizing her son. “Oh, you won so many games? You won Executive of the Year? That’s not really success. You are trying to get to here,” and he raises an invisible bar above his head for effect. “Anything under there?” he says. “It’s ordinary.”
Even if the awards didn’t satisfy him, they pointed out obvious inequities in the game. The fact that there aren’t enough Black folks on NBA sidelines and in C-suites, let alone taking home those awards? Well, that pissed him off. “We just don’t get the chance. That’s the honest truth. Why is that?” he asks, beginning to heat up. “If you really wanted to hire a Black coach or scout, be intentional! Go and find the best ones! Do the homework!”
He starts slamming his hand on a table. “Don’t just say these are the five candidates, and there are no Black people there!... It’s embarrassing when people say that I was the only Black president in all of sports. There were a few GMs, but the only Black president in all of sports? That’s disgraceful! Sports are dominated by Black people. It shouldn’t be this way. We should be given a chance.”
This morning in Toronto marks the 600th day since the Raptors have played a home game. Cross-border COVID concerns sent the team south to Tampa for a season and a half, making today something like a return to normalcy. A moment of pride. As the fans who mob Jurassic Park outside the arena make clear, times have changed. The Maple Leafs haven’t brought a Cup to Canada since the ’60s. And, respectfully, fuck hockey. Masai and the gang made Toronto a basketball town. He leads me onto the court at ScotiaBank Arena before 9 a.m. and stomps on the hardwood. “This is home turf, man,” he says. “Home of the champions.”
It took long enough. Masai came back to Toronto in 2013 for his second stint, but couldn’t quite get the team over the finish line. The Raptors kept losing in the playoffs, stuffed in a locker three straight years by LeBron James. “It’s almost the definition of insanity,” Masai says. “To do something over and over and over again and get the same result.”
So he took a few drastic, difficult steps in a moment he describes as one of the darkest of his career: He fired beloved coach Dwane Casey, replacing him with Nurse, then a mostly unknown assistant. And then he traded DeMar DeRozan, the longest-tenured player in franchise history, in a mega-deal for Kawhi Leonard, who was almost certain to leave the team the following year. DeRozan had dinner with Masai in Vegas two days before the deal, and thought he’d be coming back to the Raptors. The decision ate Masai up. “As human beings, I rank them as two of the top [people] that I have ever dealt with in the business. They are good, incredible people,” Masai says. “But we had reached a certain place. [The losses] were just going to [keep happening] over and over.... It was time to make a change. How else are we going to get Kawhi to choose here? We had to make a trade. And you have to choose that kind of a player. That was the window for us.”
It didn’t make the decision any less agonizing. He knows how much damage it caused, how it still stings now. It sounds like he’s barely forgiven himself. “It remains one of the toughest things I’ve ever done,” he says. “I hate the part that does not show humanity, that does not show empathy or sympathy in some kind of way. But we are in a game all about winning in a competitive sport. And that’s what I want to do, is win. So this is the hardest part for me. I still don’t even know how to talk about it.”
And as far as how he delivered the message? He feels remorse, of course. DeRozan hasn’t been shy about publicly expressing how hurt he was by the deal: getting the call while watching Equalizer 2 in a movie theater, ignoring Masai’s calls until later that evening, when he was told he’d be playing for San Antonio and the news would be released the next morning. DeRozan sat outside of a taco joint, on the curb, for hours, until he called Kyle Lowry.
Masai argues that there’s no good way to tell a man he has to move his family from a place he’s laid roots. This is not a typical concern in the merciless world of NBA deals. Sure, he can be a ruthless executive, but he doesn’t have the Belichickian reputation for bluntness. “If you call a player and promptly tell him, don’t even ask him how he’s doing—there’s something cold to that,” he says. “It doesn’t matter how you do it, how you deliver the message; you are still trading the person. You can sing ‘Kumbaya,’ give roses, do whatever you want, but it’s still the same message.”
Toronto finally had the goods to reach the next level, to win a championship. And Leonard taught Toronto how to win. “You saw it in [Kawhi’s] demeanor and how he interacted,” Masai says. “When we lost in the regular season, he just brushed it away and went on to the next thing. He knew the league in and out.” What ensued was so magical, Canadians enshrined it on murals in Toronto’s airport: first the four-bounce Hail Mary to beat the Sixers on Mother’s Day, in seven games; and then stunning the Warriors in six, in the last game at Oracle Arena, to win it all.
“I walked out on the court to go and see my wife after the championship,” Masai remembers. “She was on the edge of the stands, and we hugged and cried and laughed. Those moments we thought would never come, they were no longer dreams. They were right there.”
But those dreams soured. In what’s now a well-documented incident, an officer shoved Masai twice as he tried to show credentials to get onto the court, and grabbed him by the arm, telling him to “back the fuck up.” Masai, angered, pushed back. As tensions were escalating, Lowry, Toronto’s starting point guard, ran to pull Masai away. Following an investigation, prosecutors decided not to pursue criminal charges related to the incident, but the officer would later file a civil suit seeking damages, claiming in part that Masai had injured him. Masai later filed a countersuit, including in evidence footage from the officer’s body camera that appeared to undercut his account of the incident and cast doubt on his allegations. Both lawsuits were dropped last February.
“Everything became so disappointing,” he says now. “The biggest moment of my life, and you have this happen to you.” He takes a breath. “When I look back at it, I see I lost a moment. But some people have lost their lives.”
There’s a silence as those last words sit in the air. The moment still replays in his mind, two and a half years later. I ask him how he thinks about it now. “What it tells me is that it doesn’t matter who the hell you are, it’s real. Sometimes you just think it cannot happen to you. You think you are being careful, you are doing the right things; you think you are in the right place, and you just cannot imagine this happening to you. Now I know it can happen to anybody this color,” he says, pointing to his hand.
So that day he made a pledge, to himself and his people, with no fear in his heart or strain in his voice. “I have to be in front of that now. I can’t be crying about what happened. We have to move on and try to find solutions and speak our minds. I take this personally. I need to be on the forefront finding solutions.... It’s not just what happened to me; it’s how do we help others so this doesn’t happen to them?” Then he breathes in deep. “So they don’t lose their lives.”
We pull into the arena a few minutes before game time, passing Drake’s two-tone Rolls Royce as we swerve into a tunnel underneath the stadium. Masai heads to his usual couch in the video room. Now and again, he peeks his head out of the bottom of section 115, near the tunnel players run through to get on the court, and takes in the ruckus. There he stands, stoic, arms folded and half a smile apparent under his mask. Drake's “six-six-six” loop hits the speakers, and geeks in OVO gear bounce like they’re waiting for a new Supreme drop.
The Raptors lose to the Wizards, but Masai isn’t torn up about it. This is what happens to young teams, he’ll tell me later. He’s in it, as ever, for the long haul. Masai sticks around for the entirety of the game. He’s confident in the team he’s building, in the way his organization zigs instead of zags. Losses like this don’t mean much to him, not this early in a season. He’s building a lasting ideology here. To hell with a few stumbles: Have you seen Scottie Barnes (currently the surprise favorite to win Rookie of the Year) play ball? Or how hard this team digs in on defense? The Raptors might not contend for a title this year, but Masai’s kingdom up north appears secure. And besides, there’s something he wants to show me after the crowd dies down.
Close to midnight, we rush through the underground tunnels connecting the arena to Union Station, where Masai recently commissioned an art installation titled “Humanity”– it’s a large metal cylinder covered with words like Love, Unite, and Consideration. He stands for a few minutes in the quiet of the night, as rain begins to tap the concrete under us. His wife, Ramatu, greets him with warmth. “Almost won, eh?” They giggle together.
While they’re still laughing, two young men interrupt Masai’s happy moment to ask for a picture. “Okay,” he says. “But hurry up before it starts.” One of the guys, Laks Sivapalan, bows in front of Masai, showing deference to the king of the north, then whips out his phone camera. And almost like a bat signal, a crowd forms, begging for a minute with the man who willed Toronto to glory.
His wife flees for a cab and promises to catch Masai at home. The rain really starts coming down now, and he bids me adieu before too long, as well. Eventually, it’s just me and Sivapalan, who is gazing worshipfully at Masai.
“He is everything to Toronto,” the 24-year-old native tells me. “This guy had offers everywhere and stayed. He didn’t have to stay here. He didn’t have to choose us. But he embraced us. He’s taking pictures with fans; he’s bringing basketball to Africa; he went from a rebuild to a champion and keeps rocking with us.”
Jubilation suddenly blooms on the guy’s face.
“I wouldn’t trade him for anything in the world,” he says.
