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First hire by Masai Ujiri ultimately succeeds him.
Published Aug 18, 2025 • Last updated 3 minutes ago • 3 minute read
Toronto Raptors general manager Bobby Webster.
Toronto Raptors general manager Bobby Webster. Photo by Jack Boland /Toronto Sun
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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.
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And so the long-time Toronto Raptors general manager, who was the first hire, albeit in a lesser role, by Masai Ujiri back in 2013, will take over as head of basketball operations for Ujiri, who was fired as president by the club in late-June with a year remaining on his contract.
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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.
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“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, the 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 skillset and strong reputation as a basketball mind and dealmaker.
Still, Pelley had said at a media conference just after Ujiri’s departure was announced that CAA 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.”
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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, in fact leading those talks. He also, as a salary cap expert given he actually helped write a previous version of the collective bargaining agreement while working in New York, was heavily involved in strategic decisions over the years.
“I’m grateful to Keith, to the board, and to our ownership for this opportunity — the chance to continue the work that I love, for a team, a city, and country that’s become home,” Webster said. “The things that are important to me — a deep love for basketball, thoughtful and empowering leadership, and a competitive fire – are the pillars of who I am as a leader. That’s what you’ll see from me every day. This is a new chapter in Raptors basketball, but one thing that will not change is our passion for winning, and our goal to bring another championship to Toronto.”
Toronto has won 341 games since Webster became GM, ninth-most in the NBA, including franchise-record 59 and 58 win campaigns, along with the championship.
“He has incredible integrity. He knows the ins and outs of basketball and the luxury taxes as good as anybody does in the league based on his time at the league office,” Pelley said of Webster.
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