Apparently, Masai Ujiri likes torturing himself. At the moment, it’s not clear why. We’re in Studio K-O, a box-fit training facility on King Street west of Bathurst. Not 20 minutes ago, having just landed on a delayed flight from Chicago, Ujiri drove up in a black Chevy Suburban. In the change room he donned shorts and zipped a camo-patterned nylon hoodie to his neck. Now, his hands encased in 12-ounce boxing gloves, his playlist of Nigerian Afrobeat music throbbing around him, Ujiri pounds the thick mitts his trainer wears on her hands as she moves around the room calling out punch combinations. He repeats each combo 15 or 20 times for 30 minutes, giving it everything he has, while his trainer introduces footwork and body movement to mimic a fight. Halfway through, he’s hanging off a heavy bag like a man clinging to life itself.

Listen, we can all agree on the value of a good, hard workout. What the 49-year-old Ujiri is doing here is something different. “I’m struggling a little bit,” he admits. No wonder. For one thing, after a busy summer, this is his first boxing session in months. For another, it has been five days since Ujiri has taken any solid food. Daily fasting—nothing more than tea from 7 a.m. to 7 p.m.—is something he does periodically throughout the year as a spiritual exercise. “Like the Muslims,” he says (Ujiri is Christian). Periodically, like now, he undergoes a more intense cleanse, subsisting for days solely on a “juice” of lemon, apple cider vinegar, cayenne, maple syrup and a few other nutrients, concocted by one of the Raptors trainers. “I can’t wait to eat real food tonight,” he says. (It will likely be tilapia grilled by his wife, Ramatu; it almost always is.)

Why does he do this? It’s for his players. “I tell them it’s my way of keeping up with the team,” says Ujiri. An NBA season, with its relentless grind of playing, practising and travelling, is an exhausting ordeal for the players. “When I put myself through this,” he says, “I’m trying to see how they think when they’re tired.” During the playoff run, when the pressure and fatigue were building for his players, Ujiri sometimes increased his workouts to two hours.

I am with you, he was saying. I know what you’re going through. He was also gaining insights that might help him make better decisions about his players. Right now, as Ujiri grimaces through a series of boxing crunches, throwing jabs from a sit-up position, he is trying to help the Raptors win.

Let us consider the unusual summer that kept Ujiri from his boxing workouts. Late on a Thursday night in mid-June, in Oakland, California, he achieved the pinnacle of his career when the basketball team he’d been running for six years won a championship. That night, Ujiri and his team celebrated into the morning at Epic Steak, a San Francisco restaurant. Then he travelled to eight African countries in support of two causes: his own foundation, Giants of Africa, which runs basketball camps for hopeful youths, and the NBA’s global outreach program, Basketball Without Borders, of which he is a director. He stopped off briefly in Rwanda to visit his friend, President Paul Kagame. (Ujiri declined to say how many current or former world leaders he can call up for a chat, but there are at least three: Kagame; “my guy, Kenyatta,” the president of Kenya; and Barack Obama.) And he travelled with Ramatu to Nigeria to see his parents and his friends and show them the Tiffany-made Larry O’Brien trophy his team now owned.

For a while, in the aftermath of his achievement, Ujiri was wooed by the owners of the Washington Wizards, who made it clear to him, unofficially, that they would give him anything he wanted—including an ownership stake in the company that owns the Wizards, the NHL’s Washington Capitals and various other properties—if only he would leave Toronto behind. He resisted the overtures because life is good in the city he calls home, and Washington was offering nothing he couldn’t get here. But it’s always nice to be wanted, especially given the other key element of Ujiri’s eventful summer: the fact that he was living under an oppressive legal cloud.

On June 13, seconds after courtside officials declared Game 6 in Oakland over and Kawhi Leonard began waving his arms in triumph, Ujiri encountered a zealous sheriff’s deputy as he attempted to get to the court to celebrate with his players. The details of the scuffle that ensued were a matter of investigation and review by police and the Alameda County District Attorney’s Office for four months, until it finally announced its decision not to press charges.

One thing that was immediately clear to anyone who watched the post-game scene on TV: Ujiri was shaken by what had happened. At a time when he should have been giddy with joy, he looked haunted. From her seat in the stands, Ramatu could tell something was wrong. “You could just see Masai’s face,” she says. “My husband’s face was not like him.” Family members watching from home saw it too, and began texting her: “Is Masai okay?”

In a press conference about two weeks after the Oakland incident, Ujiri insisted he respected authority. “I am confident,” he said, “about who I am as a person.”

He’s a winner, for starters. He arrived in Toronto in the spring of 2013, took over a team the league did not respect, and talked immediately about winning a championship. Then he did it. In the process, he injected the city with a bolus of pride. We had felt winning before. But when the Blue Jays won, it was summer; the city was dressed for company, and we were thankful the Americans weren’t seeing us at our worst. The Raptors played when the wind howled and our streets were crusted with grey snow, and they told the Americans to deal with it. With “We the North,” this team held the winter, our secret shame, to their hearts.

That was Ujiri’s doing. When he arrived, he told his team what he wanted in a brand. “I wanted it to be about being proud of who we are,” he says. “Being proud of Toronto and Canada. We’re not afraid of the cold, and we are going to fucking win here.” We the North was developed by the Sid Lee agency based in Montreal. It had already been rejected by that city’s soccer franchise, the Impact, when Ujiri claimed it for Toronto. “I saw it, and it gave me goosebumps,” he says. Us too.

Ujiri is also a builder. Since 2016, the Raptors’ home has been a $37-million practice and workout facility now dubbed—since Drake bought the naming rights—the OVO Athletic Centre, which sits next to Medieval Times at Exhibition Place. At its heart lies an enormous practice court. The offices that surround it are like beachfront property, with views of the court going to the highest-ranking executives along one side and coaches along the other. Fingerprint scanners control access to every section, while computerized sensors on the walls of the court can track every shot for close analysis. This centre exists because Ujiri told Maple Leafs Sports and Entertainment the team needed it. Done.

Steps away from the Raptors war room, where trade and draft discussions are aided by a ring of about 20 computer monitors, sits Ujiri’s large, narrow office furnished in brown and cream leather, where images of Barack Obama and Nelson Mandela intermingle with pictures of Ujiri’s wife and two children, six-year-old Zahara and three-year-old Masai Jr., nicknamed “Ding Ding.” Ujiri doesn’t seem to spend a lot of time here. He does much of his work in his car as a driver ferries him to and from his home in North York, which he bought immediately after being named president. At the OVO Centre, he would rather be moving, meeting with players and coaches, talking on his BlackBerry or roving among the desks of his small front-office team, which operates like a kind of executive hydra, its many heads working as one, discussing roster and development matters.

He is a man of convictions. In addition to fasting, Ujiri prays frequently—“I pray to God to look over us,” he says—and considers the two acts spiritual rather than religious. Effort matters to him. He has a scout’s eye for those who will give more of themselves to the cause. “He’s a quick study of people,” says Stan Jones, associate head basketball coach at Florida State University, who has been friends with Ujiri for about 17 years. “He picks up on people’s character, and he carries himself with an unbelievably high level of character that allows you to realize how genuine he is.”

His players see that in him. “He values the little things about a person more than just their basketball talent,” says Fred VanVleet, the Raptors’ emerging star point guard. A few years ago, during the NBA’s summer league—a series of games that allows teams to assess new players—VanVleet was an undrafted kid trying to make the Raptors and playing tentatively. Ujiri was watching. At the end of one game, he pulled VanVleet aside. “He told me, ‘Be assertive. Don’t be shy out there.’” He gave VanVleet instructions for how to improve. “I was taken aback that the president of a team would say that to me,” he says. “I took it to heart.”

For Ujiri, a player’s response to that kind of push goes a long way to determining whether he is a Raptor. The team that won the championship reflected Ujiri’s character-first ethos—the first team in NBA history to win it all without a single top-14 draft pick on the roster. It was a team of players who, at first, didn’t seem to possess the most talent. What they had were depths of resilience and determination. They were a team of Masai Ujiris.

In Zaria, the city in northern nigeria where Ujiri grew up, he was called “Bones” and “Mosquito” by his playmates because of his matchstick-thin legs. There was another name for him, too, coined by a friend named Gideon: “The Boy is Good.” An odd sort of nickname, it followed Ujiri as he grew to excel at sports, partly because Gideon repeated the phrase so often and partly because it seemed to touch on some deeper quality than Ujiri’s skill with a ball.

Ujiri’s best friend, Dennis Ogbe, had been afflicted with polio, his right leg weakened and his left leg paralyzed. By the time he met Ujiri when they were eight or nine, he was coping with a leg brace, a wheelchair and crutches, and the bullies they attracted. “Meeting Masai was a turning point,” says Ogbe. “He has so much compassion and he likes to treat everybody equally.” Ogbe couldn’t run, so during soccer games, Ujiri appointed him the goalkeeper. Whoever owned the ball set the rules, and they were usually playing with Ujiri’s ball. His family was more affluent than most in the area; his Kenyan-born mother, Paula, was a doctor, and his Nigerian-born father, Michael, was a hospital administrator. They had arrived from Bournemouth, England, when Ujiri was nine months old. The two boys met when Ujiri’s family moved to Samaru, a village on the western edge of Zaria, where Ujiri could attend the primary school that was part of Ahmadu Bello University. Ujiri and Ogbe became a team. They flew kites. Collected pigeons. To get to their drama club, which was many kilometres away, they would often share Ujiri’s Scorpio bicycle, working out a system by which Ogbe pedalled with his stronger right leg and Masai his left. Later, Ogbe taught Ujiri how to drive.

As a boy, Ujiri was introduced to basketball by Oliver B. Johnson, known to most as “Coach OBJ.” An American who’d been in the Peace Corps, he had stopped off in Nigeria in 1969, set up some basketball uprights and started coaching the kids who came around, one of whom, in the early ’80s, was Ujiri. It was then, according to the coach, that the boy began to “feel his dreams.” Ujiri dreamed of playing in the NBA, and he would watch games on VHS tapes to learn moves. His ambition took him to prep school in Seattle, then junior college in North Dakota. But the NBA was a dream too far. “I wasn’t good enough,” he says. He was a scrappy player, effective defensively, but he lacked offensive skill, and at a narrow six foot four, he lacked size. Instead, he played professionally in Europe for six years, and after bouncing from his fifth team, he quit.

Trying to figure out his future, he called David Thorpe, a development coach and ESPN analyst he’d met a few years earlier. He wanted to get involved in the business side of basketball, he said. He knew a lot of African players, and thought maybe he could help with recruitment. Did Thorpe have any advice? “First you have to meet people,” Thorpe told him. College basketball’s Final Four was scheduled for the following month in Atlanta. Thorpe told Ujiri to find a place to stay and meet him there, and he’d introduce him around.

There is a loaves-and-fishes quality to Ujiri’s way with introductions that weekend in 2002. He lacked a cellphone, so he frequently borrowed Thorpe’s. Soon, says Thorpe, “I was getting lots of phone calls from famous coaches I didn’t know.” They all wanted to talk to Ujiri. “Clearly he had charmed a lot of people and he had something to sell, which was good players in Africa.” That weekend, Ujiri made more than 20 solid connections with coaches who were interested in the players he knew.

He worked with Thorpe on a document they called Masai’s Sphere of Influence, which showed all the countries where Ujiri had played or knew people. He used that, and his charm, to land a volunteer international scouting job with the Orlando Magic. The team would give him the credentials to gain access to gyms around the world, but promised nothing more. Ujiri grabbed it.

For months he travelled across Europe, covering his own costs, borrowing money from his mother and Ogbe to survive. He slept on friends’ couches. Used Delta Buddy Passes to get cheap flights. At the end of a year, deep in debt, he submitted his expenses to the Magic and received a cheque for $3,000, a fraction of what he’d spent. “It broke my heart when I got it,” he says. The position may have cost him financially, but he’d built equity in knowledge and connections, meeting people everywhere he went. At one point, before the start of an NBA game at the Meadowlands in New Jersey, he spotted Adam Silver, then the president of NBA Entertainment. He walked up and started sharing his impressions about the league. When Ujiri left, Silver turned to a colleague and said, “Do I know him? Who is he?” Today, Silver, now the NBA commissioner, is one of Ujiri’s closest friends. The effect of talking to Ujiri, he says, was “almost comforting.”

Within a year, Ujiri had won a paid, full-time scouting position with the Denver Nuggets. He bought a house in Phoenix to be near friends and became known as a guy who went everywhere, attended every event and had a fine eye for talented players who were engaged in the game. At about the same time, he started his Giants of Africa basketball camps in Nigeria, initially as a way to unearth players with NBA potential.

Four years later, at a pre-draft event in Orlando, someone tapped him on the shoulder. He turned to see Bryan Colangelo, president and GM of the Raptors, who wanted to know if Ujiri had any interest in working in Toronto. Colangelo, who’d recently been named Executive of the Year, was basketball royalty at the time. “I was like, ‘Oh my God, this is Bryan Colangelo talking to me,’” says Ujiri. He took a job as director of global scouting in Toronto, and for the first time, he worked in an office every day, wearing a suit. “I was like a sponge,” he remembers. “I had to learn the salary cap. I had to learn the business side of the game. I had to learn trading. I had to learn how to talk on the phone to other executives. I learned all that from Bryan Colangelo.” In 2008, he was made an assistant GM.

Ujiri left his belongings in Phoenix and built a new life in Toronto from scratch, living in the SoHo Hotel. It was during this first stint with the Raptors that he met Ramatu Barry in Washington, D.C., where she sold men’s sportswear at Saks Fifth Avenue. They began dating, and she saw how late he worked. One night, she asked why he wouldn’t come to bed. “Bryan has a big meeting in the morning, so I need to provide all these numbers for him,” he explained. She said, “Masai, you work so hard at night. Why can’t you be the GM?” He looked at her and laughed. “It’s not that easy,” he said. Ramatu told him that he had to believe in it, and they would pray about it. In 2010, Ujiri became GM of the Denver Nuggets.

He arrived facing an enormous challenge: the Nuggets’ best player, Carmelo Anthony, wanted out. Ujiri had never made a trade in his life, and for his first act, he had to trade the franchise star. Ujiri nailed it, getting a return of players from the New York Knicks that a CBS analyst called “tremendous” and “stunning.” In 2012–13, the Nuggets went 57-25, and Ujiri was named Executive of the Year. That was when Tim Leiweke, then president of MLSE, came calling.

A sports executive with a history of winning in Los Angeles, Leiweke had recently arrived on a white steed to slay the morose dragons of mediocrity that had settled in at MLSE. Colangelo’s Raptors had missed the playoffs for five straight years and seemed Leafs-like in their acceptance of losing. Leiweke saw Ujiri as an agent of change. “He had the same kind of juice and determination that I did,” says Leiweke. “A desire to be great wherever he went.” Leiweke told Ujiri what he wanted him to do—“Change the culture, win a championship”—and he offered to chop away the deadwood of the existing front office before Ujiri arrived. With his memories of his first stint in Toronto still fresh, Ujiri gave him a list of the people he wanted gone, some of them executives who had been there for years. “I let 14 people go in one day,” Leiweke says. “It was one of the harder days I had there.”

Ujiri hired Jeff Weltman, who’d been his boss in Denver, as his executive VP of basketball operations. He added Bobby Webster and Teresa Resch, who had experience in the league office, and Dan Tolzman, who’d climbed the scouting ladder in Denver. “Those were my guys,” says Ujiri. The only bit of deadwood left over was Colangelo himself. Leiweke had given him a face-saving role as president of things-that-had-nothing-to-do-with-basketball. Ujiri knew it was hard for his former boss. “You go through the emotions of that person losing his job, and you feel for him,” he says. But apparently there were no hard feelings on Colangelo’s part. “He wanted me to take the job,” says Ujiri. Three weeks later, Colangelo resigned and left Ujiri unencumbered.

In person, Ujiri presents an unusual mix of self-assurance and vulnerability. He seems slightly wary of personal questions and skirts negativity as if it might cling, but he swears and smiles freely, and whatever he says has a raw sincerity, as if it comes from somewhere deep. Perhaps because of that, praise for his leadership abilities knows few bounds. When people who know him try to unlock the essence of his leadership style, they gravitate to the word trust.

“He values trust.” —Fred VanVleet

“There’s enormous trust between us.” —Adam Silver

“He trusts us to bring things to him that we know he would care about.” —Bobby Webster

For Ujiri, the keys to being an effective leader are simple: hire smart people, let them work and hold them accountable. He ranks the skills of others above his own, and the more he talks about his staff, the more fervent he gets. “I believe in them, and they make me better,” he says. “I pray God I’ve given them opportunity. ’Cause they all deserve it.”

His affection for his front-office team is palpable. He says of Resch, with conviction, “That’s my boss.” When he catches sight of Tolzman walking into the common area outside his office, his eyes light up. “DT!” he shouts and raises a fist, grinning widely. Friendship seems energizing for Ujiri. It brings out his playfulness. Told that his close friend Weltman, now the president of the Orlando Magic, would not respond to interview requests for this story, Ujiri juts his chin insolently. “Fuck him. Write that. No, I’m kidding! That’s why we beat their asses in the playoffs. I’m kidding! Don’t write that!” He’s giggling the whole time, his signature soft flutter.

The first five years of the Ujiri era were a dizzying mix of rising hope and crushing disappointment. He managed to erase the team’s defeatism, but not its defeats. In 2018, after LeBron James’s Cleveland Cavaliers swept them from the playoffs for the second straight year, Ujiri’s “hold them accountable” principle dictated that head coach Dwane Casey had to go. In May, Ujiri and Webster walked from the executive side of the OVO Centre to Casey’s large office on the coaches’ side. Ujiri, who considered Casey a fatherly figure, says firing him was “the hardest thing I’ve ever done.”

Four days later, at Hotel X, the team interviewed the first candidate for Casey’s job: assistant coach Nick Nurse. The executives were on edge. “It started out pretty raw,” says Nurse. Over the course of about four hours, they peppered him with a series of creative questions. At one point, during a rapid-fire round, they demanded he recount his life story in 45 seconds, then asked him if he had a sense of humour and made him tell them a joke on the spot. Nurse was so amazed by their agility that he came away thinking Ujiri’s team had either worked doggedly to prepare for the interview or had a rare natural chemistry. You can thank the boss for that, either way.

Nurse was equally impressive. “I’m pretty certain Nick mentioned winning and championships more than any other guy we interviewed,” says Tolzman. Before becoming an assistant coach with the Raptors in 2013, Nurse had spent 11 years coaching in the British Basketball League and several more in the NBA’s developmental league, winning coach-of-the-year awards just about everywhere he went. He promised to bring a new approach to player accountability. His staff would track a player’s every action on the court, then deliver multicoloured report cards at practice the next morning. He was announced as the head coach in June.

With Nurse installed, attention turned to the roster. It was clear the team needed a heart transplant, and Ujiri’s team saw in San Antonio’s Kawhi Leonard a player who embodied talent, drive, professionalism and fearlessness. To get him, they’d have to trade away their best player, DeMar DeRozan.

The risk inherent in trading DeRozan, who was wildly popular, for Leonard, who’d spent much of the previous season sidelined with injuries, was obvious. Disaster was as plausible as success. Yet Ujiri says he gave that risk no thought at all. “I don’t consider that,” he says. “I always believe if you are very, very well-prepared, things will work out.”

Part of the preparation involved informing the MLSE board of their intentions. The NBA operates under a complex salary cap system. For the 2018–19 season, team payrolls were capped at $102 million (U.S). A team could spend more by using various exemptions, but going over $124 million (U.S.) would incur a luxury-tax penalty. The Raptors payroll was high enough that acquiring Leonard would push it over the luxury-tax threshold for the first time. With the $25-million tax penalty, their payroll would jump to just over $160 million (U.S.).

MLSE chairman Larry Tanenbaum admits he was alarmed by the idea of trading DeRozan for one year of an injured player. But Webster and Ujiri made their case, he says, “in a very studied way.” They’d prepared for hours. Using spreadsheets and a smooth verbal pitch, honed by their own constant discussion, Ujiri and Webster spelled out the financial ramifications of acquiring Leonard and the possible effects on the roster. The board had plenty of questions; the discussion following the presentation was far longer than the presentation itself. But the money holders trusted Ujiri. “His vision,” says Tanenbaum, “is a championship vision.”

The day the trade happened, Ujiri and Ramatu were in Kenya with Obama to attend the opening of a youth centre founded by Obama’s half-sister, Auma. Ujiri was on the phone with Webster late into the night, finalizing the details, and at a certain point, Ramatu announced she was going to bed. She remembers her husband telling her, “I think I’m almost done. I may have to call DeMar.” It was about 5 or 6 a.m. in Kenya when the deal closed.

The 24 games of the historic playoff run that followed produced countless thrilling moments, but there was one in particular that signalled that this team was different, that it could shake off its demons. That was Leonard’s buzzer-beating bouncing ball in Game 7 against the Philadelphia 76ers. But what led to that ecstatic moment were several potentially crushing ones, which Ujiri never saw.

It’s his habit to watch each game from various vantage points. He never sits in the stands. Rarely watches from a box. He even stopped watching from the players’ tunnel because he is constantly badgered by fans. Instead, he roams. In Toronto, he’ll watch the first part of a game from the video room near the court, then ride the elevator and watch the second half from his 15th-floor office at 50 Bay Street. On the road, he’ll sometimes take out his phone and watch from the arena’s parking lot.

As the clock ticked down against the 76ers, Ujiri was watching on the TV in his office. With just 12 seconds to go in the game and his team leading 89–86, he headed for the elevator. He wanted to get to the court to celebrate the win that would push the Raptors to the Eastern Conference Finals. During that elevator ride down 15 floors, he lost cellphone service. When the elevator opened, he started down the corridor, which gave him a view into the press room. There he saw two men staring at a screen. One of them said something, and though Ujiri couldn’t hear, he read the man’s lips: “I can’t believe this is happening to us again.”

“I read it!” exclaims Ujiri. “I read his lips saying that!” Then Ujiri demonstrates how the man placed a hand over his eyes in woe. He hurried into the team’s video room, where Tolzman was watching from the couch. “What the fuck just happened?” said Ujiri. What had happened was this: two free throws by Joel Embiid, one made and one missed free throw by Leonard, and a Jimmy Butler layup. Tie game.

The game was stuck in a long timeout. There were four seconds left on the clock. Ujiri sat down on the couch next to Tolzman and waited. When play resumed, Leonard received the ball, raced to the right corner and sent up his shot just before the buzzer sounded.

Ujiri watched the ball rise and fall. He saw it hit the rim and assumed the shot was missed. “I went, ‘Okay, overtime.’ And I got up.” He demonstrates, rising off the white leather couch of his office. “I’m walking out and I see the second bounce. And it dies a little bit. Then the third one dies almost like completely. And I’m like this.” He stands frozen in his doorway. “And I turn to the screen. And Tolzman is sitting on the couch and he too is getting up. And the fucking ball goes in.” A huge smile spreads over Ujiri’s face. “Oh my God.”

Through that triumphant year, Ujiri’s family and Leonard’s became closely entwined. According to Ramatu, Leonard’s young daughter, Kaliyah, was so taken with little Masai Jr. that at home she would constantly repeat his nickname. Apparently, at one point Leonard said, “Who the hell is Ding Ding? All my daughter keeps saying in this house is ‘Ding Ding.’”

Ramatu also recalls that at the end of the year, while Ujiri was trying to convince Leonard to remain with the Raptors, he joked, “Whether you stay or not, my son is going to marry your daughter, because they love each other.”

On the couch in his office, looking out toward the staff beginning work on the new season, Ujiri doesn’t linger on the failures of the summer. He tried hard to convince Leonard to stay, but he implies he didn’t go to extremes. “We were going to be who we are,” he says. “And Kawhi appreciated who we are. He wanted to go home.”

Now that Leonard has signed with the L.A. Clippers, and shooting guard Danny Green has gone to the Lakers, the Raptors are like a tall ship without a main sail. They’ll make do for now and hope the wind blows just right. Their roster will play elite-level defence, and it still has talent. Young power forward Pascal Siakam seems destined for stardom, and the front office has added potential in new-to-the-league players like Matt Thomas and Terence Davis.

It might be enough. It might not. Ujiri insists he’s unconcerned. More than that, he’s excited. “We’re excited about the young players we have,” he says. “We’re excited about the veteran players we have because of what they bring, the winning mentality. I’m excited about our coaching staff. I’m excited about the front-office staff. Man, we have incredible ideas and things we’re going to do, and we are so excited about it.”

The way he describes things, it’s hard not to believe in the future Ujiri sees. It’s impossible not to want to be a part of it.

This story originally appeared in the December 2019 issue of Toronto Life magazine. To subscribe, for just $29.95 a year, click here.