Masai Ujiri's Future Looms Large Over Raptors' Offseason

Before the Toronto Raptors get started with any major offseason activities the organization is going to need answers about Masai Ujiri's future
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There will soon be time to rehash the 2020-21 season for the Toronto Raptors and look forward to what should be a much better 2021-22 season, but the biggest and most pressing question for the organization right now involves the future of team president Masai Ujiri.

This week Ujiri and Maple Leafs Sports & Entertainment will reportedly begin negotiations on a contract extension, according to the Toronto Sun's Steve Simmons. How that will go or what specifically Ujiri wants in a contract is anyone's guess. The 50-year-old former NBA Executive of the Year has tightlipped about his future, refusing to give any indication of what lies ahead for the organization in the not-to-distant future.

Here is what we do know about Ujiri and his future.

For one, he said he's not worried about the future of the organization. Whatever that means for his future with the organization is unclear, but with general manager Bobby Webster signed to an extension, head coach Nick Nurse in place for years to come, a core group of Fred VanVleet, OG Anunoby, and Pascal Siakam under contract, and the city of Toronto behind the Raptors, Ujiri is confident the future for the Raptors is bright.

It's also clear that replacing Ujiri is going to be challenging. He's brought a credibility to the organization that had once been an afterthought in the NBA landscape. If Kyle Lowry is the greatest Raptor of all time, as Fred VanVleet said, Ujiri might be No. 2 on that list.

"His leadership on the court, off the court, what he means to us as players, and the demands. He challenges every player and he rewards most of the players when you do what he asks you to do," VanVleet said. 

Within the organization Ujiri has been fully committed to everything the Raptors are doing, VanVleet said. Ujiri said he would never let his future uncertainty impact his decision making as an executive and from what VanVleet has seen that's been true.

For Nurse, Ujiri has been an ideal boss. He's well-connected throughout the game of basketball, not just in the NBA but around the world. He's competitive, Nurse said, speaking and thinking in terms of championships and success at the highest level. Maybe the most important thing is that Ujiri is approachable, Nurse said. The two can have candid conversations about how they see the roster coming together and the future of the organization without ever feeling uncomfortable.

"Which isn't that typical with any boss, employer-employee relationship I don't think," Nurse said, "especially in sports and especially in coaching."

At some point, likely soon, Toronto is going to get an answer about Ujiri and his future. Within the NBA, it's believed that it'll take a lot to pry him away from Toronto, Marc Stein of the New York Times has reported. But, at the same time, ESPN's Adrian Wojnarowski has reported there may be options outside of the NBA calling for Ujiri.

Keeping him in Toronto will be crucial for the team's long term success, but even if he does leave, he's done the best he can to leave the Raptors in good hands for many years to come.

Further Reading

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Chris Bosh receives the call to the Basketball Hall of Fame

Jalen Harris is looking forward to spending the summer developing with the Raptors