Under normal circumstances our sports pages would be filled with Leafs and Raptors playoff coverage, and how the Blue Jays look in the first month of their season. But these aren’t normal times. Instead, with the games on hold during the pandemic, we’re launching an occasional series: Hindsight In 2020, which digs deep into some of the most significant moves and moments in Toronto sports history and examines their lasting impact. Hirings and firings, trades and non-trades, things you knew a little bit about or didn’t know at all. We’re kicking it off with a behind-the-scenes look at the hiring of Masai Ujiri, architect of the defending champion Raptors.

In winning Canada’s first NBA championship last season, they elevated themselves to the status of legend. They’ll all get a share of the eternal credit.

You know the names. They’re etched on the banner. They’re engraved on the rings.

But a name that’s gone unmentioned is Jed Hughes. Who’s Hughes? Not only did he lead the executive search that placed championship architect Masai Ujiri atop the Raptors hierarchy. He was in charge of the operation that brought Tim Leiweke to Toronto as CEO of Maple Leaf Sports and Entertainment — a seismic move that spurred more than just basketball success. As the vice-chairman at Korn Ferry, a global headhunting firm, Hughes has undoubtedly had more of an impact on the Toronto sports scene than anyone so devoid of a public profile.

Which is fine with Hughes. He’s a behind-the-scenes operator who’s been playing matchmaker between organizations, executives and coaches for more than a decade. A former football coach at both the NFL and NCAA level, he helped pair Pete Carroll with the Seattle Seahawks and Andy Reid with the Kansas City Chiefs before they both helped bring Super Bowls to those franchises. As we at the Star look back on some significant moments in Toronto sports history as a distraction during this moment of sporting standstill — and Ujiri’s arrival as president of basketball operations in 2013 stands among them — Hughes’s role amounts to one unexplored detail of a championship picture.

Bringing Leiweke to Canada in the spring of 2013 — this in the wake of his abrupt departure from AEG, the international sporting conglomerate based in Los Angeles — was hardly a given. When Larry Tanenbaum, the MLSE chairman, expressed interest in Leiweke as CEO more than a year after the departure of Richard Peddie, Hughes and his firm were brought aboard to convince Leiweke to consider what some saw as an unlikely move.

“There you are living in Los Angeles and Hollywood, and you’re moving to Toronto — it’s a culture change, not only a temperature change,” Hughes said in a recent interview. “We eventually got it done, but it was a difficult negotiation.”

Let’s not forget: March of 2013, when the pursuit of Leiweke began, was a difficult moment in Toronto sports. The Maple Leafs hadn’t made the playoffs since 2004, the longest such drought in the NHL. The Raptors were en route to missing the post-season for the fifth straight season. And as much as the 2011 arrival of head coach Dwane Casey set the program on the rise, there were decisions to be made.

“Tim came in and made a lot of changes and upset people,” said Hughes. “Larry Tanenbaum and (Raptors GM) Bryan Colangelo had a very close relationship. And Tim came in and changed that ... He thought that in order to move basketball where they needed it to be, they needed a change in leadership.”

As changes to the landscape go, Leiweke’s presence amounted to an earthquake roiling beneath a hurricane. Moving past Colangelo was only the beginning of a radical transformation Leiweke would engineer during a tenure that lasted a little more than two years.

“Tim is a guy who doesn’t sit still. He’s always stirring the pot. He’s always on the cutting edge of disruption,” Hughes said.

When Leiweke needed help finding a replacement for Colangelo, he turned to Hughes. While there emerged a list of potential candidates — among them Tommy Sheppard, then vice-president of basketball operations with the Washington Wizards, and Kevin Pritchard, GM of the Indiana Pacers — Hughes said it was Ujiri, then GM of the Denver Nuggets, who quickly emerged as his No. 1.

Raptors fans can thank heavens that Leiweke, who briefly pondered the merits of bringing in his friend Phil Jackson, never got too far down that road.

Denver, on the surface, seemed an odd place to poach an executive. The Nuggets, in the regular season that ended in 2013, won 57 games. George Karl would be named NBA coach of the year. Ujiri was executive of the year. But those in the know understood a few things. Ujiri, at the time, was in the final year of a contract that paid him one of the lowest salaries among top basketball executives, about $450,000 (U.S.).

“All I know is very early in that season, from my half a dozen friends in the NBA management area, I was told by three or four of those guys that Masai was out. He was going to Toronto,” Karl said in an interview. “I think everybody in our locker room felt that. We were having a great year. So I don’t think we were necessarily distracted by it. But I’m not a fan of negative energy, and I think that was negative energy.”

That Ujiri might have options beyond the Mile High City wasn’t exactly a news flash. The previous year, Ujiri turned down an offer to take the top job with the Philadelphia 76ers: $2 million a year for four seasons. And speculating that Ujiri might one day end up in Toronto, given that Colangelo was widely seen as running out of rope and given Ujiri’s previous three-year run as Toronto’s director of global scouting, wasn’t exactly a reach. But as for the notion that Ujiri was an executive with one foot out the door all season, there are many who saw it differently, among them Pete D’Allessandro, now an Orlando Magic executive who was Denver’s vice-president of basketball operations at the time. D’Allessandro scoffed at Karl’s characterization.

“Masai was all-in on that team and that season — that’s who he is. There was never a feeling he was looking beyond Denver. That’s not how he operates,” D’Allessandro said.

Ujiri, for his part, declined comment. League sources say that in the wake of the Sixers courtship, he discussed a pay raise and an eventual extension with Nuggets ownership, although nothing was finalized. When Leiweke first approached Nuggets president Josh Kroenke, son of owner Stan Kroenke, with a request to speak with Ujiri, he was initially denied permission. But Leiweke persisted, and the Nuggets eventually relented.

Still, Karl’s notion that Ujiri’s move to Toronto was somehow prearranged seems a stretch. For one, as Hughes said, Tanenbaum was close to Colangelo; even as Leiweke insisted the GM be ousted from the basketball operation, it was Tanenbaum who supported Colangelo’s striking of a three-year deal to head the business side, a doomed idea that lasted all of a month.

For another, Leiweke and Ujiri had never been introduced before the spring of 2013. Their first meeting happened at Leiweke’s home in Vail, Colo. And from the get-go, the story goes, they hit it off. Leiweke paid immediate respect to Ujiri’s passion, discussing at length Giants of Africa, the charitable organization Ujiri founded that uses basketball to enrich the lives of African youth. Ujiri, sharing Leiweke’s taste for chronic optimism, pointed out the many positives of the Toronto market.

And after a day spent together, they got quickly to the details. Ujiri had non-negotiables if he was going to be pried from the Nuggets, including a list of executives he’d need to hire, most of whom still make up his inner circle. He insisted the club build a practice facility and acquire a team in the NBA’s development league. Not 30 minutes after Ujiri left his meeting with Leiweke, Hughes called with an offer that met all of Ujiri’s demands and included a five-year contract at about $3 million a season, plus $200,000 a year for Giants of Africa.

An agreement was reached. And while there were complications — the Kroenkes took their time letting Ujiri out of his deal — there was no real doubt. Ujiri was announced as Toronto’s executive vice president of basketball operations on May, 31, 2013. And he’s more than delivered. There’ve been six straight playoff appearances culminating in last year’s title. There’ve been difficult decisions, to swap out Casey for Nick Nurse, and DeMar DeRozan for Leonard. Even his occasional detractors can’t deny the success.

“I think he’s one of the best gatherers of information in the NBA. I think he has great relationships in the NBA from the league office to agents to players,” Karl said. “Probably the connection he doesn’t have is with coaches. He has Dwane Casey and George Karl on his ‘What the hell happened?’ list. I think coaches are always leery of those guys … In the same sense, whatever decisions he’s made, he’s made them work. And I respect that.”

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Hughes calls Ujiri “probably the No. 1 sought-after executive in the NBA,” which has already become a problem for the Raptors. His contract is up at the end of next season, if and when next season comes. Covetous competitors have been lurking. The Ujiri-to-New York rumours have died down for now, but until he’s signed — assuming NBA life one day returns to normal — it’d be foolish to believe he won’t continue to be linked to other potential landing spots.

“The reason he’s in demand: He’s one of a kind,” Hughes said. “I’ve done executive searches in all the sports, and he’s unique. He’s able to connect with lots of people, and not everyone can do that. He can talk to the usher as well as he can talk to the ownership group ... Very few people have a combination of intellect, IQ and (emotional intelligence). He’s got that combination of all those that allow him to be so much in demand.”

So much in demand and not yet under a long-term deal. Fans in Denver can tell you how that scenario ended in Toronto’s favour seven years ago, thanks in no small part to Hughes.

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