Masai Ujiri

The Toronto Raptors put up a valiant title defense this season, but their hopes of repeating came to an end earlier this month, when they were eliminated in the second round of the playoffs by the Boston Celtics in seven games. With a number of key players, including Fred VanVleet, Serge Ibaka and Marc Gasol, hitting free agency this summer, the Raptors have some big decisions to make about the future. 

So, too, does the man making them. Raptors president Masai Ujiri, who has established himself as one of the best executives in the league, will see his own contract expire in 2021. And as of yet, he has not had talks with the team about an extension -- something he disclosed Thursday during a press conference. Via the Toronto Star:

"Honestly, coming out of this (season), things are a little raw. I'm going to reflect a little bit and we will address it when it's time to address it. It's not something I'm going to do in the media and publicly, with respect. But no, I haven't had conversations."

In regards to his key free agents, Ujiri noted that they are a "priority," but didn't dive into too much detail about the team's plans, though that isn't exactly a surprise. This will be an interesting summer for Ujiri and Co. as he tries to set up the best possible future for the team, despite the fact that he might not be a part of it. And all while navigating the uncertainties created by the coronavirus pandemic, including an unclear timeline for the 2020-21 season, and major questions surrounding the salary cap moving forward.

Ujiri has been with the Raptors since 2013, when he signed as the GM shortly after winning Executive of the Year for his work with the Denver Nuggets. In 2018, he assumed more responsibility, taking on the role of president of basketball operations. During his time with the franchise, he's turned the Raptors into a perennial playoff team and notably swung the blockbuster trade for Kawhi Leonard that helped Toronto win their first title in franchise history. 

While he may still remain with the Raptors, and has plenty of time to discuss an extension, his comments on Thursday will only fuel suspicion that he may move on when his deal is up. Given his resume, he could have his pick of jobs across the league if he decides to take on a new challenge, but the most notable possibility involves the New York Knicks.

The Knicks have been after Ujiri for years, and those atop the organization are reportedly "obsessed" with him, according to Ian Begley of SNY last year. It's not clear whether he has any interest in going there, and the prospect of working under James Dolan isn't exactly enticing. From a neutral observer perspective, however, Ujiri trying to fix the Knicks would be a fascinating prospect. 

For now, though, his focus will be figuring out what to do with this Raptors team, and that's a big enough challenge for the moment.