Raptors stay in house, choose Webster as head of basketball operations

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Maple Leaf Sports and Entertainment did its legwork before coming around to what was the obvious decision from the beginning: Bobby Webster was the man for the job.

And so the longtime Toronto Raptors general manager, who was the first hire (albeit in a lesser role) by Masai Ujiri in 2013, will take over as head of basketball operations from Ujiri, who was fired as president by the club in late June with a year remaining on his contract.

The move came Monday, six weeks ahead of the start of training camp. The organization ultimately decided not to choose a president at this time, instead keeping Webster as GM, but deciding to “officially hand the team to Bobby,” MLSE president Keith Pelley said in a statement ahead of a media call with Webster.

“Going through this comprehensive process this summer and meeting with external candidates played a critical role in arriving at this decision as it made clear that we already have the right person leading the Raptors in house,” Pelley said.

“After spending time together this summer in Las Vegas, I was very impressed by Bobby’s leadership style, his rapport with the players and staff, his reputation with his peers across the league and — especially and importantly — his vision for the Raptors. This team is his now to lead and I know we all look forward to what comes next.”

Webster, a 40-year-old Hawaii native who spent years working in the NBA’s head office and also interned for the Orlando Magic before joining the Raptors, is extremely well-regarded around the association. It would have made little sense to hire someone above him given his varied skill set and strong reputation as a basketball mind and deal-maker.

He certainly seems appreciative.

“There’s 30 of these jobs in the NBA, but this one, to me, is one of one … I just really think that there’s not a more unique basketball job in the world,” Webster said on a media call.

Pelley had said after Ujiri’s departure was announced that Creative Artists Agency had been hired to conduct a search and that while Webster would be considered for the job, the Raptors would be looking for a president who “will need to be a prominent, successful business leader.” That person, Pelley admitted, would have “big shoes to fill” given Ujiri’s achievements in Toronto.

That said, Webster was a major contributor to those feats too, most notably the 2019 NBA title, which was driven by Kawhi Leonard. Webster played a massive role in getting the Leonard trade done with San Antonio and in fact led those talks. As a salary cap expert given he actually helped write a previous version of the collective bargaining agreement while working in New York, he also was heavily involved in strategic decisions over the years.

Webster said the major changes he’s noticed in recent weeks is more conversations with Pelley and ownership. “More personal, more direct, more consistent,” he said.

Toronto has won 341 games since Webster became GM, ninth most in the NBA, including a franchise-record 59-win campaign along with the 58-win championship season.

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While recognizing the departure of Ujiri (he said there would be no awkwardness given the relationship built over years of working closely together), Webster is pleased at the continuity with himself, assistant general manager Dan Tolzman and other key members of the front office sticking around. They are hoping the Raptors are ready to turn a corner.

“With this team and with this specific point in time, it is ready to make the next step,” Webster said.

Franchise player Scottie Barnes has already said they will return to the playoffs, but Webster wouldn’t go as far as making any proclamations. He is eager to see what Darko Rajakovic does with more talent at his disposal and how a healthy Brandon Ingram elevates the group.

Webster is far more low key as a presence than the loquacious Ujiri, who was seemingly born to be a public speaker, but is prepared to show more of himself as the top dog.

“I probably view it as an opportunity for me to sort of set who Bobby is, where we want this team to go. You know my personality, I’m going to lead with a smile, I’m going to lead with a lot of positivity, empower those around me, I don’t view it so much as a comparison point.”

He also mentioned on the media call that he’s done a lot of stuff “behind closed doors” versus the more public Ujiri, who was “incredibly inspirational and motivational,” he said. “But, I’m gonna be Bobby and I think people know who that is. I’ve been around the industry for a while.”

What some might not know is that Webster is immensely competitive. Under Ujiri and Webster, the team accelerated a rebuild around Barnes after the departures of Fred VanVleet, OG Anunoby and Pascal Siakam. Now the team is expected to compete for a playoff spot, given its high payroll.

Webster will have to figure out how to get the team out of the luxury tax this season (trading Ochai Agbaji, RJ Barrett or someone else would be ways to do so) and how to reignite a passionate fan base that has been frustrated by four playoff misses over the last five seasons.

Attendance took a rare dip last season, but prices continue to rise and the economic climate in Toronto has grown dicier recently. While Pelley said in June the basketball head would not be worrying about “commercials or tickets” as a priority but would instead would be focused on basketball operations, the bottom line is sales and promotion are parts of the gig. Ujiri was very good at it and it’s an area Webster will have to master, too.

We’d bet he’ll do just fine and ownership wisely felt the same.