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Court Vision
Toronto Life
|November 2025
New Raptors boss Bobby Webster must juggle the expectations of an impatient fan base, a new CEO and an oligopolistic owner. Oh, and the team has to win too
You've been the Raptors' general manager since 2017. After Masai Ujiri’s departure in June, MLSE gave you the keys. What’s the new job like?
A lot of it is a continuation of being GM: I'm in charge of the coaching staff, picking players and ensuring we have the resources to be successful: the best physical therapists, shooting coaches, and strength and conditioning coaches. The biggest change for me involves my interactions with Rogers since they became majority owner in July.
Does having this level of responsibility take you further away from building a winning team on the court?
It does take me a bit away from basketball, but I’m motivated by managing people, finding the best talent and getting the best out of them. In school, I was the captain of every team I played on. I studied economics at UC Santa Barbara and graduated when I was 20. I became the Raptors’ GM at 32. We won a championship when I was 34. I’m 40, and I just finished my 20th season in the NBA. I've accomplished a lot in a short time.
The casual fan may not know that you're originally from Kailua. What's the culture of Hawaii hoops like?
This story is from the November 2025 edition of Toronto Life.
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