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TSN Raptors Reporter

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TORONTO – By now, you can imagine Bobby Webster has become accustomed to operating in the vast shadow of Raptors president Masai Ujiri.

It comes with the territory, having spent more than seven years working under one of the most influential front office figures in all of sports.
 
Even on the day he was promoted to and introduced as the team’s general manager back in June of 2017 – with rumours swirling and yet another report of the Knicks’ interest in Ujiri making the rounds – Webster had to answer questions about the future of his boss.
 
 “There’s speculation every day,” said the then 32-year-old native of Hawaii, who became the youngest GM in the NBA that afternoon. “I don’t think I need to necessarily comment on that specifically. But the stability between [ownership] and Masai in this organization, I think, is clear and I’m happy to be part of all of it.”
 
After three-plus seasons of success in that role, highlighted by Toronto’s championship run in 2019, Webster has been rewarded with a multi-year contract extension. It’s been in the works for a while – Ujiri had suggested that it was all but done as far back as September – but was finally made official on Thursday.
 
“I think everyone knows what Bobby brings to our organization: intelligence, poise, and creativity,” Ujiri said in a press release. “I’m very pleased that our team will continue to benefit from his many skills for seasons to come.”
 
“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 added.
 
It’s another big moment for Webster and his family, and one he earned on his own merits. However, it should come as no surprise that, once again, the question on most people’s minds is – what about Masai?
 
Ujiri’s current deal is set to expire at the end of this season and there’s been no indication that an extension is imminent, or even that meaningful negotiations have taken place.
 
There are likely multiple reasons why those discussions were pushed back. One of them, which Ujiri has cited, is timing. With everything going on around the world, amid a global pandemic and racial unrest, as well as inside of the organization – namely its relocation to Tampa – he didn’t feel it was appropriate to be ironing out the details of his next contract.
 
Another factor was his stated goal of getting his leadership group taken care of before addressing his own contractual status, a process that began with the extension for head coach Nick Nurse in the fall and would seem to be wrapped up now that Webster has a new deal.
 
With the coach and GM locked up long term – as well as three franchise cornerstones in Pascal Siakam, Fred VanVleet and OG Anunoby – the attention rightly shifts to the architect of the club, and arguably its most important member.
 
The ball is in Ujiri’s court, so to speak, and it has been for some time. The Maple Leafs Sports & Entertainment ownership group will have a pen waiting on the boardroom table whenever he’s ready and willing to sign on the dotted line. But even now, with the team settling into its temporary home and his staff secure in their roles, it’s still unclear what tops Ujiri’s list of priorities. Only the man himself knows for sure.
 
“I don’t know what the timeframe will be,” Ujiri said back in December. “I go into this thing with a very positive mind and attitude, and we hope it goes that way.”
 
Whether Ujiri has been ensuring that all the pieces are in place and his people are rewarded before making his own commitment, or whether he’s laying down a succession plan on his way out remains to be seen.
 
While it’s natural to wonder what Webster’s extension means for Ujiri, if anything, that shouldn’t take away from the importance of retaining a talented young executive. That’s a win for the Raptors, in and of itself.
 
Now 36, Webster has a bright future ahead of him, and at some point that future will be in the lead chair. He isn’t Ujiri, but he doesn’t have to be. He’s more reserved by nature, which is why he’s comfortable going about his business outside of the spotlight, and it’s why he and Ujiri have complemented each other so well for so long.
 
He’s been a crucial part of the front office team that has overseen the most successful era in Raptors history, same as assistant general manager Dan Tolzman, who also doesn’t get enough credit, and several others. They’ve all had a hand in just about everything the franchise has accomplished over the past seven years, and other teams have taken notice.
 
These days, Ujiri’s isn’t the only name that comes up when another club has an opening. One of the league’s most coveted execs, Webster had been linked to the Chicago Bulls’ job last season before they hired Denver’s Arturas Karnisovas to run basketball operations. You can bet that other teams have come calling, as well.
 
The hope, for Raptors fans and the organization alike, is that the tandem of Ujiri and Webster will continue to lead the organization into its next era. Regardless of what Ujiri does next, though, securing Webster ensures that they’ll be in good and capable hands for years to come.​