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For the Toronto Raptors vice-chairman and team president, failure is not an option. And under Masai Ujiri, the Raptors have won more than they ever have in franchise history

anthony gebrehiwot/The Globe and Mail

Masai Ujiri was alone on the team bus when he first saw video of the moment that upended his life. This is unusual in and of itself. As Toronto Raptors vice-chairman and team president, the 52-year-old father of three is rarely by himself. He has the slightly alarming schedule of an extreme achiever: wake up at 4:30 a.m. to do an intense workout (no coffee), then spend the day pacing the halls of the Raptors’ practice facility, conspiring with general manager Bobby Webster, shuttling across Exhibition Place to the office of his charity, and attending the various events, meetings, practices and games that keep him flanked by employees, colleagues, and admirers for most of the day.

During the 2020 playoffs in the Orlando bubble, however, with COVID-19 restrictions at their height, Ujiri was all on his own when he was finally sent footage of the altercation in Oakland, Calif., that had been hanging over him for more than a year.

The facts of what happened are well known: As the Raptors celebrated their first NBA Championship in 2019, Ujiri tried to make his way to the court and was stopped by Alan Strickland, an Alameda County sheriff’s deputy. The two got into an altercation. The sheriff’s office requested that Ujiri be charged with battery of a peace officer, though the district attorney never pressed charges. Strickland sued Ujiri, saying he’d struck him in the face with both fists, though the accusation felt absurd on its face. And then it stayed that way for more than a year: the word of a law enforcement officer against Ujiri’s.

On the bus in Orlando, he watched newly released body cam footage and saw what everyone would soon see: Ujiri approaching Strickland with his hand in his pocket to pull out his credentials and the sheriff’s deputy pushing him violently—once, and then again, even as Ujiri explained that he was the Raptors president. Incontrovertible proof.

On the bus, Ujiri thought, Wow. This is really what happened. In the months since the incident, he had begun to doubt his own memory. Did I hit him first? he wondered. He’d seen movies about the innocently accused, and he’d never understood how people could come to question their own experience in these situations. Now he understood.

He went to the arena. He watched the game but hardly watched the game. Then he called a car and went back to the hotel. “As soon as I got to the room, I just started crying,” he says.

Ujiri tells me this in his office at the OVO Athletic Centre—the gleaming $30-million cube that Maple Leaf Sports & Entertainment, which owns the Raptors, built when Ujiri told them the team needed a world-class practice facility if it wanted to attract world-class talent. It’s early September, just before the start of the pre-season, and most of the players are already back in town, gearing up for another campaign. On the other side of the office wall, Pascal Siakam is draining pull-up jumpers over the outstretched arms of a trainer, the thump of the basketball and the squeak of sneakers audible.

On the eve of his 10th season with the team, Ujiri has the air of a man who has already won everything and is now trying to do the harder thing—win again. He’s doing it from a position of enviable security. Ujiri is the face of the franchise—a role generally held by the people who actually play the games—and enjoys a level of trust from both ownership and fans that is perhaps unique in the league. He is, after all, the guy who came to a losing team and brought it a championship. He’s the executive who came to a franchise that many dismissed as small-market and instead saw “a goldmine”; under his leadership, the team’s valuation has increased by 517% and become one of the 10 most valuable franchises in the league.

On the sidelines that night in Oakland, however, all that success meant nothing. He was just a man, a Black man, who needed to be put in his place. And that’s part of the reason that even now, years later, the memory still hits him so hard. “It’s even getting to me now,” he says, his eyes welling up for a moment.

People close to him say they’ve never seen him more emotional than in the days after the video was released. He couldn’t sleep. But when he got on the phone with his team in Toronto, it was to get them working. “What can we do?” he asked. He wasn’t talking about his own case; that had been put to rest. “What are we going to do?”

In both basketball and business, the word “leadership” gets thrown around a lot. It’s a term overused to the point of meaninglessness, applied to any executive who might plausibly deliver a TED Talk or any athlete whose contributions aren’t captured by the box score. One simple way to think about it, however, is as an act of transmutation: the ability to take a group of people, with their own individual ambitions and desires and fears, and turn them into a single unit working toward a common goal.

Masai Ujiri has many qualities as an executive. There’s the dealmaking that makes other execs wary of trading with him (transforming middling guard Greivis Vásquez into two key players on a championship team remains a shocking robbery, even seven years later). There’s the brand-building that turned the “We the North” Raptors into Canada’s Team. There’s the eye for talent that saw future All Stars in unheralded prospects like Siakam and Fred VanVleet. But those who work with him say it’s Ujiri’s ability to connect with people and inspire them toward a collective purpose that is his singular genius.

“He’s incredibly charismatic,” says Webster. “He makes you feel like you’re a part of what he’s part of.” In 2013, Webster was a 28-year-old salary-cap wunderkind working at the NBA head office. He’d been offered other front office jobs, but Ujiri was the one who convinced him to make the move and join him with the Raptors. Teresa Resch, now a vice-president with the team, was also part of that original team. Ujiri had only met her a few times, but he’d made an impression on Resch. “He’s a great connector,” she says. “He’ll meet you and you’ll feel like you have a connection with him.”

She and Webster both insist that this is just who Ujiri is. “He’s always been like this,” says Webster. But the fact is, when Ujiri walks into a room today, his story precedes him, and that story has its own power. Before you meet him, you know the broad outlines. Ujiri was a skinny-legged kid from Zaria, a city in Nigeria, who found basketball as a teenager and managed to grind out a playing career in England, Denmark and Finland. He was a charming striver who parlayed a few contacts into an unpaid scouting job with the Orlando Magic, couch-surfing across Europe on his own dime. And he was the front-office savant who made the NBA equivalent of the mailroom-to-CEO ascension in record time—scout and then quickly assistant general manager. The first African-born GM of any major North American sports team. NBA Executive of the year. World champion.

Here’s a dumb-sounding observation about Ujiri: He only cares about winning. This is both a boring sports cliché and a colossal understatement—like saying a polar bear only cares about hunting, when the real story is that if a polar bear stops hunting, it literally stops being a polar bear. But his need to win is such a totalizing way of looking at the world, not just basketball, that it’s worth trying to understand.

“Maybe the best way to explain it is that failure is not an option,” Ujiri says in his office. But failure is an option. In a basketball season, only one team wins. Everyone else loses. So how do you handle that? “I don’t handle it,” he says. The miserable season the team spent playing in Tampa because of COVID-19 restrictions, for example? A season in which the Raptors, in fact, mostly lost? “That was a winning season,” says Ujiri emphatically. “Because we got Scottie.” And Scottie Barnes—the grinning, preternaturally gifted Rookie of the Year who Ujiri picked against conventional wisdom? Scottie is winning personified. “When we interviewed Scottie Barnes, he mentioned the word ‘winning’ I think it was 27 times,” says Ujiri. He looks at me meaningfully; 27 times is a lot of times to say the word winning. “In my head, I said, Oh my god. You know? Winner.”

In most other people, in most normal walks of life, this winning obsession might read as borderline delusional. When they arrived in Toronto together in 2013, Resch remembers Ujiri hitting the same note every single press conference: We will win here. “I think at first people were kind of like, ‘Well, I don’t know,’” Resch remembers. The city seemed pretty content with losing. The organization’s rhythms and business strategies were built around steady mediocrity. Opening day was the biggest day on the calendar because the team never made the playoffs. You had to reward the season ticket holders with a big event early in the season because the basketball wasn’t reward enough. But Ujiri kept saying it, says Resch. “Then people started believing it.”

Under Ujiri, the Raptors did win, more than they ever had in franchise history. And that was enough until it wasn’t. Ujiri remembers watching the closing minutes of Game 2 of the 2018 second-round series against the Cleveland Cavaliers. That was the series in which LeBron James once again coolly demolished Ujiri’s team, and the term “LeBronto” trended on Twitter to signify James’s complete ownership of the city.

“I remember walking to my office on the 15th floor,” says Ujiri. The Scotiabank Arena was empty, the offices abandoned and dark. They were only down two games, but Ujiri could feel it: They’d had a chance, and they’d let it slip away. The greatest regular season in Raptors history, all the progress—it meant nothing if they lost. That’s when he made an oath. “I looked in my office, and I swore to myself that we would fucking win in this place, man,” he says. “I’m gonna fucking win.”

What followed is both the most triumphant and the most painful period of Ujiri’s tenure. He fired reigning coach of the year Dwane Casey, a man he considered a father figure. He traded DeMar DeRozan, a beloved fan favourite, for Kawhi Leonard, an inscrutable superstar who some thought might not even show up in Toronto. On the night that trade went through, Masai was in Kenya, on the tail end of a trip that began with him opening a basketball court with friend and former president Barack Obama. It was 3 a.m., and he paced back and forth in the hotel, building up the courage to tell DeRozan the news.

The standard GM response to a transaction like that is that it’s “just business”—a phrase meant to artificially demarcate the personal from the professional, as if the two weren’t always messily entangled. Ujiri doesn’t pretend anything is just business. “When I look at those guys,” he says, gesturing toward the court outside his walls, “when I stand out there and look at those guys, they believe in me. And I believe in them.” What he means is that to succeed as a team, there can be no barrier between a business relationship and a friendship. You need to connect. And yet…you also need to win.

Exactly how to square those two needs is something he’s still working on. “It’s very hard for me,” he says. “Extremely hard.” But the thing about those personal connections is that they can persist, even when the business relationship is done. He reaches into his pocket and pulls out his cellphone. It’s Kyle Lowry—greatest Raptor of all time and ex-employee after being traded to Miami in 2021. He’s texting Ujiri late in the night because his kid is playing football now, and the proud father just had to send his friend a video. Ujiri still gets these texts from Lowry. He stays in touch with Leonard, too. “Even now, DeMar. After all of that, you know? It’s better.”

The most obvious way for Masai Ujiri to keep the relationships and avoid the unpleasantness? Leave the basketball side of things behind. In 2022, you can see a clear non-NBA path laid out for him, if he wants it. His charity Giants of Africa continues to grow, and each offseason Ujiri leads camps and builds basketball courts across the continent. He moderates panels at United Nations conferences, hobnobs with politicians, has multiple world leaders on his phone—not just Obama but Justin Trudeau and President Paul Kagame of Rwanda. Success has brought with it a certain gravitas, and at times he carries himself more like an ambassador or statesman than a basketball executive.

Nick Nurse has noticed the evolution. The Raptors head coach first met Ujiri in England, where Nurse was coaching the Birmingham Bullets and Ujiri was just a scrappy guard for the Derby Storm. Over the years, they kept bumping into each other out on the outer rim of professional basketball employment—as coaches and scouts in tournaments around the world, both trying to make it to the big leagues. “He was super hungry,” says Nurse. Today he has less to prove. “He carries himself with a lot of confidence. Not that he didn’t before, but it’s a calmer confidence now.”

One evening in early September, I follow Ujiri to a Giants of Africa event in a soaring atrium in downtown Toronto. Ujiri created the event, AfriCAN, as a networking for African professionals in the city and to help fuel economic development on the continent. Afrobeats music fills the space while more than 300 jubilant guests drink from an open bar and eat small plates of fried sea bream and spiced beef gumbo. Raptors forward Precious Achiuwa and rapper Shad bump elbows with Uber drivers and small business owners. The whole thing feels like an outgrowth of Ujiri’s animating philosophy: If you can connect people, bring them together, who knows what you might achieve?

Ilyas Adiris, a tall 29-year-old Somali-Canadian actor and filmmaker, stands by himself, nursing a drink. Like so many in the crowd, he’s come because of Ujiri. Not just his work leading the Raptors, but his work in Africa. “Masai Ujiri is my idol,” he says. “As weird as this might sound, I want to be the Somali version of him.”

Chef Marc Kusitor has business cards for his Afro-Caribbean catering company ready to distribute. His day job is working in food services at the Scotiabank Arena, but he has bigger dreams. And seeing Ujiri, an African, as the leader of the organization is inspiring. “Every day I walk into work proud of where I work,” he says.

When Ujiri enters the room, he is immediately surrounded. He eventually takes to the stage, looks out on the crowd and seems genuinely moved. “I am apologizing to all Africans in Toronto for not doing this sooner,” he says.

There are not many executives who inspire this kind of devotion; there is no equivalent crowd of ambitious young people waiting to be inspired by Galen Weston. It’s not at all difficult to imagine Ujiri taking his unimpeachable Q score and bringing it to a different sphere. Politics? Philanthropy? He loves basketball, but there are so many other things he cares about, too, so many other people he wants to connect with, causes he could lead.

Could Ujiri build a career outside of sport? “I think the more interesting question is, would he want to do all of that without the basketball?” asks Webster. Ujiri’s answer is clear. The basketball is what makes all this possible. The winning is what gives him the platform he needs, as well as the energy. “You have to win,” he says. “I don’t want to do it without the winning.”

The last time I meet with Ujiri, it’s at a corporate speaking gig in a hotel ballroom filled with accountants and tax consultants. He and his people arrive at the Royal York Hotel and move through the space like a practised SWAT team—his security guard John scoping out the hallway, his publicist locking step with him as they head toward the elevator, assistant trailing behind.

Backstage, Ujiri is introduced to the organizer. He’s introduced to the stage manager, to the person who will introduce him, to the woman in a blazer who won a company-wide contest to interview him onstage and who now, frankly, looks terrified, staring blankly into the middle distance clutching a water bottle. Ujiri looks them each in the eye and smiles, touches his hand to his heart. And then he’s out to a standing ovation from a ballroom full of mostly middle-aged, mostly white accountants in lanyards.

Everyone here is trying to do the same thing I am—glean leadership knowledge from someone who is very good at leading. We all want to understand what makes him a successful executive, a winner, and to take that knowledge home with us in a few digestible, transferable lessons.

On stage, Ujiri is happy to oblige. He busts out some of what I’ve come to recognize as core Masai-isms. “Show more passion than ambition,” he says, an elegant index finger raised in the air. “You need an organization that’s full of leaders,” he says, so hire people who are smarter than you. “Win,” he says, over and over. “We win on the court. We win off the court. And when you do, you bring other people along.”

In the ballroom, this all goes over great. Ujiri has figured out how to take his genius for personal connection and reproduce it at scale. I would, if I had the money, definitely pay to have him come inspire a few hundred of my favourite accountants.

But it’s impossible not to feel like there’s something missing. Asking Masai how he leads is, in the end, as unsatisfying as asking a great player how he plays basketball. Some alchemy of natural talent and countless hours of hard work? Instinct and experience? There are gaps in the narrative that don’t have satisfying answers. He went from scout to GM because…he was doing a really good job scouting? And those gaps, unfortunately, are best filled with the qualities that sound like the clichés of basketball press conferences and business self-help books. A passion so intense it spills over to those around him. An overwhelming need for success. A genuine instinct for human connection that looks at a stranger and sees a future teammate.

Here’s what Ujiri did after the Oakland footage became public: He tried to take his personal experience and turn it into something bigger.

He couldn’t stop thinking about the people who got tangled up in the criminal justice system and didn’t have what he had—the best lawyers in the world, money and celebrity. His team found a group called The Bail Project, a non-profit that pays bail for people, and he made a big donation. But that kind of help-at-a-distance is never enough for Ujiri. He doesn’t just want to fund a basketball camp in Mogadishu—he wants to be out on the court with the kids. So Ujiri flew out to Chicago.

In his office, he tells me the story of the man he met there. This isn’t something he’s really spoken about before, not something he did for publicity, but we’ve somehow gotten here, and now he wants me to understand what the encounter meant to him.

So the man, let’s call him Sid, is diabetic. He’s gay and has a loving partner. And during the pandemic, Sid lost his job, lost his insurance and began rationing his insulin. “He had one of those attacks, you know?” He was out on the street, acting erratic, and he tried to enter a car he thought was his own. The police arrested him. For days he was in prison. “His partner could not find him.” Eventually the bail project intervened. They found him in the system, paid his bail, brought him home.

That was the man Ujiri flew out to meet. He walked into his apartment. “The first thing I saw was bananas. He loves bananas. I love bananas,” says Ujiri. “He has two watches on. He loves watches. I love watches.” Sid loved photography, just like Ujiri. And they had both, in their own way, had an experience with the law that made them feel as if everything they’d worked for in their lives could be taken from them. That was something they talked about, too. The two men were objectively extremely different. But all Ujiri could see when he walked in the door was what they had in common.

I ask him: What was the purpose of that meeting? What did he hope it would achieve, for either of them? He seems genuinely baffled by the question. The value is, to him, self-evident. “Well for me, I found a friend,” he says. “I think he did, too.” Now, when he goes to Chicago, he checks up on Sid. That’s one more person on his team. He made a connection—another link in Ujiri’s vast and growing chain of personal relationships. The benefits go without saying. That’s how you win.

10 Masai moments

May 31, 2013

Ujiri joins the Raptors as president and GM of basketball operations.

July 10, 2013

Ujiri wastes no time undoing the work of previous administrations, sending underperforming No. 1 pick Andrea Bargnani to the New York Knicks for a trio of players and three draft picks.

December 9, 2013

Ujiri sends Rudy Gay to the Sacramento Kings midway through the season. Led by DeMar DeRozan and Kyle Lowry, the team wins the Atlantic Division and makes the playoffs for the first time in six years.

April 16, 2014

Before the team’s first playoff series in years, the Raptors release the “We the North” campaign, which takes the team’s outsider status in Canada and turns it into a rallying cry.

April 19, 2014

Three days later, Ujiri yells “f--- Brooklyn!” to pump up the crowd. The outburst earns Ujiri a fine, but it puts the sleepy Raptors into headlines and brings a new swagger to the fanbase.

May 11, 2018

Following three straight seasons that end with a playoff loss to the Cleveland Cavaliers, Ujiri fires coach of the year Dwane Casey. After an exhaustive search, the team promotes untested assistant Nick Nurse.

July 18, 2018

In Ujiri’s biggest swing yet, he trades beloved Raptor DeMar DeRozan, prospect Jakob Poeltl, and a draft pick for Kawhi Leonard and Danny Green.

February 7, 2019

Midway through the season, Ujiri tinkers with the roster, trading a package centred around Jonas Valanciunas for veteran Marc Gasol.

June 13, 2019

The big moves pay off, and the Raptors win the 2018-19 NBA championship.

July 29, 2021

After Ujiri’s worst year leading the Raptors—a disappointing season playing in Tampa due to COVID—the team is rewarded with the fourth pick in the draft. Ujiri selects Scottie Barnes, who goes on to win Rookie of the Year.

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