“I view this as the beginning of our next long Raptors run”: Meet Bobby Webster, the team’s new general manager

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.

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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? It’s about playing smart and playing hard. We didn’t have the most naturally talented players, and we weren’t blessed with size, so when we’d go to the mainland to play, it was about skill and not making mistakes.

There are only 30 people in the world who get to have your job. What’s your edge? All of my players are younger than me, and most of my staff is older than me. I’m a bridge between the two. I try to relate to players about their upbringings. My skillset has allowed me to exist in a lot of worlds. That’s probably what separated me as I grew up in the industry.

Your contract was extended until 2027, which isn’t long in the basketball world. You have a lot to do in short order. What’s the goal in those two seasons? We have a young, talented team. Other than Brandon Ingram and Jakob Poeltl, most of our guys are still approaching their primes. That long runway gives us a chance to build chemistry and camaraderie, which is exciting. I view this moment as the beginning of our next long Raptors run, hopefully culminating in another ring.

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You were Masai Ujiri’s first hire when he joined the Raptors in 2013. Why do you think he was let go with one year left on his contract? You’d have to ask him and ownership. It’s not fair for me to speculate.

MLSE’s new CEO, Keith Pelley, has said it was his decision to fire Ujiri. But there were rumours about friction between Ujiri and Edward Rogers. Do you think the decision came down from the top? Rogers is a massive media company. I’m sure there are some decisions that Edward gets involved in, but I don’t know how involved he is. I’ve worked with him for 12 years at the board level, and everything was always professional. He’s supported us whenever we needed help. There have been no contentious interactions.

The Raptors became a cultural phenomenon during the We the North era. What’s it going to take to get them back to that status? Winning gets people talking. When you walk the street, you still see just as many Raptors hats as those of any other Toronto team. That passion is embedded in the DNA of the city. It’s also about the players. The story of former Raptor Kyle Lowry and how hard he played resonated with Torontonians. And longevity matters. All the failures we had in the 2010s created a nice story arc for the championship. The romance of the heartache, the big losses, the big wins—they’re all part of the journey. That’s what we’re trying to build again.

If you were trying to woo a big-ticket free agent, where would you take them for dinner? For players, it has to be Jacobs and Co.—incredible steaks and impeccable service. We took our top prospect, Collin Murray-Boyles, there. For a meeting with someone like a head coach, it’s always Joso’s: the best seafood in the city.

Given the success you’ve had before hitting middle age, what advice would you give a teenage Bobby shooting hoops in Kailua? Don’t be the squeaky wheel. Learn how to solve problems, and stay out of the fray. It’s a misconception that those who make the most noise are the most rewarded. People will notice you if you’re hard-working and humble.

This interview has been edited for length and clarity.