Now That GM Bobby Webster Has Re-Signed, The Toronto Raptors World Is Waiting On Masai Ujiri

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The Toronto Raptors surprised nobody by signing General Manager Bobby Webster to a multi-year contract extension on Thursday.

Webster is well respected in the Raptor organization and was one of the main architects of the 2019 NBA Championship team.

The larger question is whether President and CEO Masai Ujiri follows up by signing his own contract extension now that he is in the eighth and last year of his contract in Toronto.

Ujiri’s future status is the biggest unknown in the organization. But Ujiri has said in the past that he wanted the rest of his lieutenants to get their names on a contract before he makes a decision.

Webster, 35, is one of the bright, young faces of the NBA. The native of Hawaii was named Raptors GM in June 2017. He joined the Raptors after working in the NBA league office in New York the previous seven seasons.

“I think everyone knows what Bobby brings to our organization: intelligence, poise and creativity,” Ujiri said in a statement. “I’m very pleased that our team will continue to benefit from his many skills for seasons to come.”

As per team policy, terms of the agreement were not announced.

The signing of Webster follows the multi-year signing of coach Nurse Nurse back in September.

“It’s great to be able to continue the work of building the next Raptor championship team — a goal which is part of our organizational DNA,” Webster said in a statement. “I’m grateful to Larry Tanenbaum, MLSE ownership and leadership, our great players and staff, and the people of Toronto for making this my home for the past years, and for the future.”

Webster has been the trusted right-hand man of Ujiri. He’s been part of the key decision-making processes involving the best deals this organization has made, including the trade acquisition of Kawhi Leonard in 2019.

With Webster locked in long-term, the attention will turn to Ujiri, the 50-year-old Nigerian-Canadian.

It’s believed Ujiri would want several guarantees in place for him to stay. Money will, of course, be a big part of it. It’s believed he could command more than $12 million a season and become the highest-paid executive in the NBA.

But perhaps the president’s job is too small for Ujiri.

He has deep interests outside of basketball, including charity work involving Giants of Africa, which he founded in 2003 with the goal of discovering basketball talent. He also serves as director of Basketball Without Borders, which promotes basketball throughout the continent.

Before Ujiri got to Toronto in the final days of former president Bryan Colangelo’s run with the club in 2013, the Raptors were never considered a championship contender. The team was insecure about itself in the Toronto sports environment, which is passionate about the Maple Leafs and Blue Jays.

But Ujiri molded this team quickly and turned it into a championship team, with energy and bravado.

It’s to Ujiri’s benefit that he waits until the time is right to make his decision. He’s earned the right to leverage his assets to get the best contract he can. No doubt a big part of any negotiation will be an out-clause so that, if he signs long term, there will be an escape clause at some point.

Ujiri has been known as a thoughtful and deliberate decision maker. He has spoken publicly about his contract situation, but only in the broadest terms.

There may be a long list of suitors. There were reports back in 2019 that the Washington Wizards were preparing a significant offer.

But it’s thought the list of teams that can afford him are short: The New York Knicks, the Brooklyn Nets, the Chicago Bulls, the Los Angeles Lakers and Clippers and perhaps the Miami Heat.

If Ujiri’s past is any indication, he may work to the end of his current contract in Toronto and move on to other opportunities. Just as he did when leaving Denver for Toronto.

Now that Webster is signed long term, perhaps there is no time pressure on Ujiri to make a decision. But the longer the situation goes on, the more anxious Toronto fans will feel.

Ujiri brought Kawhi Leonard and a championship to Toronto. Fans don’t normally cheer for executives, but if Ujiri leaves at the end of the year, fans across Canada will feel a deep sense of loss.