The Nigerian has endured one of the least likely paths to success, from playing street soccer in his hometown of Zaria to swapping text messages with buddy Drake on the state of the NBA's only Canadian franchise.
And although the Raptors are enjoying a great run this season -- sitting comfortably in second place behind the Eastern Conference-leading Cleveland Cavs -- Ujiri is anything but complacent.
He is, after all, representing two countries and an entire continent.
"Failure is not an option for me," he reiterates in a typically relaxed manner that masks his intense work ethic. "There is a huge weight for me, even if it is for the continent of Africa to succeed; to succeed for my organization, and to succeed for the NBA. I think it's huge."
Given how he's beaten the odds so far, it would be foolish to bet on Ujiri's failure in any context -- even on galvanizing a team which hasn't advanced past the first round of the playoffs in 15 seasons.
Like all the other kids in his area, Ujiri grew up playing soccer, though he followed the NBA on VHS tapes provided by a mentoring American coach. At 20, he moved to Seattle as an exchange student and scrapped his way onto two lower-division college basketball teams.
What little money Ujiri saved from his playing career in Europe -- which included stops in basketball outposts England, Denmark and Finland -- would soon be blown on traveling to and from Africa as an unpaid talent-sniffer for the Magic, among other teams.
In 2003 the Denver Nuggets hired him as a full-time scout, launching his career as a league executive.
In the ensuing decade, Ujiri would be hired and rehired to work in the front offices of Denver and Toronto, climbing the corporate ladder rung by rung.
Ujiri is now in his second stint with the Raptors, where he served as assistant general manager until 2010 when the Denver Nuggets made him the first Africa-born person to run a major North American sports team.
His first big move was to engineer the Nuggets' trade of disgruntled Carmelo Anthony to the Knicks -- a deal widely regarded as a heist for Denver.
In 2013 the Raptors hired him back with a five-year, $15 million deal to take over duties as both president and general manager, a ringing endorsement for his ability to spot talent and motivate those around him.
Considering Ujiri's background as an international scout, it's not surprising that the Raptors boast the largest number of non-American players in the NBA.
Seven of the team's 15 roster spots are occupied by the likes of Argentine veteran Luis Scola, Lithuanian center Jonas Valanciunas, Congolese forward Bismack Biyombo and a pair of Brazilian youths, Lucas Nogueira and Bruno Caboclo.
Frigid Toronto has had its challenges preserving talent since its inception 20 years ago.
Its most famous players -- Vince Carter, Tracy McGrady and Chris Bosh -- all departed in their primes, and the team is flying high this season behind a roster of largely anonymous overachievers, save for one-time All-Stars DeMar DeRozan and Kyle Lowry.
On the upside, the organization has found its niche, selling the city's multicultural hub and rabid fan base to international players looking for a slice of home.
"There is something about the city of Toronto, there is something about the country, and there is something about the whole atmosphere that's unique," says Ujiri. "You can see it with the fans, you can see it with the whole organization, it's just different."
Caboclo, who is in his first year in Toronto, was pleasantly surprised by the city's large Brazilian community, and the 20-year-old frequents a churrascaria (Brazilian barbeque) only steps from his home.
Nogueira, a multi-linguist who stands seven feet tall, compares Toronto to his previous destination, Madrid.
"It's very similar in terms of immigrants and international community," he says. "Compared to other teams like Minnesota or Milwaukee or Philly, this is a very big city and there are lots of things to do."
The Raptors have also embraced their diverse fan base in a manner so far unseen in North American sports. Indeed, attending a Raptors game is a night-and-day experience from that of its co-tenant at the Air Canada Centre, the NHL's Toronto Maple Leafs.
"When you go to a hockey game -- and don't take this in a negative way -- 99% of the people are white," says Nav Bhatia, a New Delhi-born Sikh who is the Raptors' most visible fan.
"But come to a basketball game, it's all shades, colors and everything."
Like a number of other immigrants in the city, the Indian -- who is commonly known as the "Turbinator" or simply the "Superfan", and is greeted courtside by nearly every notable player, coach and referee in the league
-- signed up for seats in the franchise's inaugural 1995-96 season, enduring many years of hardship and heartbreak.
While the team struggled with attendance in the late 1990s, Bhatia -- who worked as a car salesman when he arrived in 1984, and now owns a string of dealerships in the Toronto area -- saw an opportunity to reach out to his community. He offered to pay for thousands of tickets, while hosting a Diwali night to celebrate the ancient Hindu festival of lights with a halftime show.
Now he also hosts a Baisakhi Day for his fellow Sikhs, capped by a baby elephant delivering the game ball at center court.
On game night Bhatia, who made the trip to London along with a publicist to organize his engagements as a team ambassador, can be found sitting in his customary baseline seat, one of 20 season tickets he owns which cost him upwards of $400,000 annually.
"Bhatia truly represents the new wave of Torontonians who have gravitated towards one of the fastest growing sports in the world," says Natasha Alibhai, a Raptors diehard born in Karachi, Pakistan who moved to the city in 1997.
A few years later she created a Raptors-obsessed blog and eventually found work with the team in social media.
"I needed to find a way to connect to the city and the people," Alibhai reflects. "Sports has been that connector for me and many other immigrants.
"Basketball felt more accessible and affordable (than Canada's No. 1 sport hockey), as the team was in its infancy. It was the perfect time to jump on the wagon."
Bhatia calls his love affair with the Raptors "a win-win situation for both of us, my community and them."
"I want to salute the Toronto Raptors for being such an inclusive corporation, where they gave us the opportunity, but they have benefited also," Bhatia says in a 2014 Ted talk.
It should be noted, however, that not every NBA team is as interested in reaching out to its less visible surrounding communities. Nor is simply having an international base enough to keep a team afloat.
The NBA's expansion into another Canadian city with a large ethnic demographic, Vancouver, flopped. After six financially shaky seasons where the team never achieved a winning mark above 28%, the Grizzlies relocated to Memphis in 2001.
Ultimately, success on the court is key says Ujiri, who cites small-market, five-time champion San Antonio as a benchmark.
"The biggest advantage in sports is winning," he says. "Your team could be situated in the bottom of the lake, and if you build a winning culture and figure out a way to win you'll always attract everybody. Whether it's people who work for your team, or whether it's players.
"I think it's very simple: build a great culture and win. That's what we're trying to do."
Part of building that culture is making sure fans stay engaged. Although Ujiri counts Arsene Wenger as a confidant, you would be hard-pressed to find the Arsenal manager hyping up the crowd outside his team's arena for a big soccer game the way the Toronto chief has since his return up north.
For a 2014 first-round series against Brooklyn, thousands of fans gathered around a giant screen to see the Raptors lose in a crushing game seven.
The same fans returned last year before Toronto's first-round exit against Washington. In both instances Ujiri got so carried away that he had to be reprimanded by the league for cursing during the pre-game festivities -- out-of-character acts which he profusely apologized for
In the meantime, Toronto's stock is rising -- in February, it will be the first non-U.S. city to host the All-Star Game. But if Ujiri's plans come together, the city will also be hosting its first-ever NBA Finals in June -- a prospect which would send Raptors fans into delirium.
"That's our goal; that's our dream, that's where we want to go," Ujiri says. "This city is just dying for a winner, and we hope we can be it at some point."