Is Masai Ujiri Ready For A New Challenge?

Ujiri built the Raptors into a champion but could the NBA's most sought-after GM find a new home soon?

The NBA’s most coveted free agent addressed the media on Wednesday, sporting a beige tee shirt underneath a dark blazer that hung loosely on his 50-year old shoulders. Masai Ujiri won’t play a minute next season but few players, if any, hitting the open market stands as potentially impactful. The Raptors president is on the short list of any top basketball executives, one who through expert drafting, shrewd free agent signings and one franchise altering trade built Toronto into an NBA champion.

If the Raptors were a challenge, Ujiri conquered it.

Eight years in and with his contract expiring, it’s fair to wonder:

Is Ujiri ready for a new one?

Ujiri held his season ending media availability on Wednesday, and it didn’t take long for the affable exec to be asked about his status. Ujiri’s contract situation has been well known for years now, with a public pursuit by Washington in 2019 shining a spotlight on it. Ujiri has politely punted on questions about it before, indicating that his future would be addressed at the end of the season.

With the end of Toronto’s season here … Ujiri still wasn’t ready to address it.

“Nothing new,” Ujiri said. “We just finished. At some point, I’ll get with ownership here and sit down and talk, all the normal stuff. Going to weigh a few of the options and give this thing some deep thought now as I go through this process.”

Ujiri has long expressed affection for Toronto, but if that’s the case, why hasn’t he re-signed there? Surely, the Raptors, stuck in the playoff middle before Ujiri arrived, have made offers? Maple Leaf Sports & Entertainment, the parent company that owns the team, is among the NBA’s wealthiest ownership groups. Surely Toronto, with one of basketball’s best minds operating out of its front office, has handed Ujiri a blank check?

Ujiri mentioned his options, and make no mistake: those words should send chills through every Raptors fan who yearns to keep him. There are currently no front office vacancies in the NBA, though that doesn’t mean there won’t be. The Wizards at least entertained the idea of offering Ujiri an eight figure salary and an ownership slice in 2018, and billionaire owner Ted Leonsis could do it again. The Clippers enter the postseason with enormous expectations. Falling short could lead deep pocketed owner Steve Ballmer, who boldly parted ways with Doc Rivers last fall, to look to shake things up further.

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Ujiri’s interests extend beyond the NBA, putting new, potentially unexpected options on the table. The Nigerian-raised Ujiri has been a driving force in bringing NBA basketball to Africa. He has brought camps there, founded Giants of Africa, a non-profit aimed at enriching the lives of African youth, and has routinely referred to the continent as the NBA’s next frontier.

“It's time to stop thinking of Africa as a charity,” Ujiri wrote in Sports Illustrated in 2019, “and start thinking of it as an investment.”

Ujiri could be using his contract status as leverage, of course. On several occasions during a 40-minute video call with reporters, Ujiri cited the need for change. It’s clear he sees the Raptors lagging behind its rivals in key areas. He was equally unhappy about the team, which spent its entire season in Tampa Bay, being the only one displaced—and there being no guarantees it won’t happen again next season. “We do not want—I repeat—we do not want to play anywhere else but Toronto,” Ujiri said. There’s clearly a commitment he wants from ownership, one that goes beyond what he will deposit in his bank account.

“Everybody says, 'Blank check, blank check,' but I'm not as much focused on a blank check," Ujiri said. "A lot of the things that we've done here, we have to move forward as a franchise to compete with the best in the NBA. This is all about winning a championship again.”

Indeed. Ujiri knows this team is barreling towards a full rebuild. And actually—that could work in Toronto’s favor. Ask any GM: Building a team from the ground up is more fun than tweaking it after it reaches the playoffs. At heart, most basketball execs are talent evaluators, eager to dig into college prospects and mine for unheralded talent. That’s how Ujiri built the Raptors, with late first round picks (Pascal Siakam, OG Anunoby) and undrafted free agents (Fred VanVleet) added to complement its top stars. The chance to do it again, in Toronto, could be appealing.

There are key decisions to be made, none bigger than the future of Kyle Lowry. Ujiri elected not to deal Lowry before the trade deadline, but that doesn’t mean Lowry has a future there. Ujiri has a complicated, but successful, relationship with Lowry. “Kyle Lowry is obviously the greatest Raptor of all time,” VanVleet said. “And No. 2 might be Masai.” Ujiri praised the 35-year old Lowry on Wednesday (“It’s incredible what he does to keep his game going,” said Ujiri) while acknowledging a youth movement in Toronto could make Lowry a casualty.

“We have to give the young guys more of an opportunity,” Ujiri said. “We have to build. I know we won a championship [in 2019] and last year we were considered … a contender but we are at a place where we have to look at the younger players we have, maybe lift them up a little bit.”

Ujiri offered no timeline for his decision (“It will work out however the timing plays out to be.”) but this clearly will have to play out quickly. There’s a natural succession plan in place if Ujiri walks, with Bobby Webster, one of the NBA’s sharpest young GM’s who has been involved with every decision Ujiri has made in Toronto, positioned to take over. The Raptors have clean books, strong young talent with an innovative head coach in Nick Nurse to lead them. “All I know is I think we make a really good team,” said Nurse. “And I hope that team stays intact.”

Ujiri has already done the improbable, building the Raptors into a champion.

In the coming weeks we will find out if he wants to attempt to do it again.

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