Masai Ujiri

Toronto Raptors President Masai Ujiri attends a premiere for “The Carter Effect” on day 3 of the Toronto International Film Festival at the Princess of Wales Theatre on Saturday, Sept. 9, 2017, in Toronto. (Photo by Arthur Mola/Invision/AP)

  • Masai Ujiri, regarded by many as the best executive in the NBA, is a free agent at the end of 2020-21
  • The Raptors are set to continue their playoff streak but Ujiri’s future is uncertain
  • What factors will influence his decision?

The Toronto Raptors won their first title in 2019. Masai Ujiri was praised as the mastermind of the success, swinging big by trading for Kawhi Leonard to complement a roster of clever veteran pickups and smart draft selections.

The 2013 Executive of the Year is a free agent at the end of the 2020-21 NBA season. Even in an offseason which could see a raft of All-Stars hit the market, Ujiri’s future would be a major talking point. While the Raptors might not be atop the NBA championship odds for next season, Ujiri has once again built a team which should compete. He has become an icon in Toronto.

Odds on Ujiri’s future are in the table below – will he sign a contract extension before the playoffs?

Odds on Masai Ujiri Re-Signing With Toronto Raptors

Will Masai Ujiri Re-Sign Before the Playoffs? Odds
Yes -120
No -120

Odds from Dec. 8th

Contract Discussions

Ujiri and Maple Leaf Sports and Entertainment, the owners of the Raptors, have not talked in depth about a contract extension since February, as reported by Sportsnet.  It’s believed Ujiri will pocket at least $12 million per year whichever team he ends up working for.

Across his stint in Denver and his time in Canada, Ujiri’s teams have averaged over 50 wins per season on their way to 10 consecutive playoff appearances. This isn’t a man craving the glory and adulation of that success, though. Ujiri has frequently made it clear he wanted his leadership team to be signed up before he penned a new deal.

The majority of those contracts are now sorted, however, and it appears general manager Bobby Webster will be signing in the near future.

Attention turns to Ujiri – the man who finally brought Toronto a championship. He will be in demand, and he will break records for a front office salary.

The Need For Challenge

Tim Leiweke, who convinced Ujiri to leave Denver for Toronto, knows the Raptors President of Basketball Operations better than most. Leiweke spoke of Ujiri’s desire for challenge, his unrelenting ambition to achieve the next great thing. Ujiri needs unquestioned backing, complete control over basketball decisions and an organization willing to do all they can to win.

Changes to the Raptors’ ownership group could create uncertainty. It could be part of the reason Ujiri has delayed committing his future. After the glory of 2019, Leiweke warned of the Raptors becoming complacent and basking in the success of the city’s first championship. Ujiri will not settle for that.

The Raptors must remain unwaveringly committed to being the best they can be on and off the court. The organization need to allow Ujiri to challenge himself and allow him the freedom to achieve his goals beyond basketball, too.

Away from the crippling pressure of the NBA’s biggest markets, Toronto has been a perfect home for Ujiri to construct a brilliant basketball team while travelling to Africa for weeks at a time. Retaining that flexibility is thought to be key to Ujiri’s decision.

Short-Term Deal

While money might not be a priority, the salary Ujiri will command rules out the majority of NBA teams. Only a handful will pay north of $10 million for an executive and most of those teams are settled in the front office for the medium-term. Barring turmoil in the organization, it seems very likely Ujiri extends his stay in Toronto.

The desire to retain flexibility, paired with ownership’s desperation to keep him, could point to a one-year pact. Maybe Ujiri is given a longer deal with several options to cut the contract short. The future of Giannis Antetokounmpo could have an impact on Ujiri’s plans, too. If Giannis turns down the supermax, is Ujiri more likely to stay in Toronto?

With the odds split evenly, backing Ujiri to extend his stay in Toronto before the playoffs is the better value option.

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