General manager Bobby Webster will have his contract extended and take charge of the NBA franchise’s basketball operations without a change in title. The Raptors said they will not appoint a president, but Webster will be getting support from the leadership at Maple Leaf Sports & Entertainment, the franchise’s owner.
Webster said he didn’t think any kind of formal designation mattered.
“A title, to me, probably isn’t as important as your responsibilities,” he said on Monday afternoon, shortly after his extension was announced. “I’m really thankful for this opportunity. I’ll make the most of it.
“A title is not something that concerns me.”
Webster, 40, is entering his ninth season as GM in Toronto, his 13th with the Raptors, and his 21st overall in the NBA. One of the architects of the Toronto’s 2019 championship run, Webster has led the team’s overall roster building, organizational structure, and day-to-day basketball operations for years.
“There’s 30 of these jobs in the NBA but this one, to me, is one-of-one,” said Webster. “The platform you have here, the opportunity we have with Canada Basketball, with all the kids growing up in Canada playing, I just really think that there’s not a more unique basketball job in the world.”
Webster was former team president Masai Ujiri’s first hire on the Raptors when the latter was brought on as Toronto’s executive vice president and general manager in May 2013. Before being named general manager in June 2017, Webster held the titles of assistant general manager and vice-president, basketball management and strategy.
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Ujiri was officially dismissed from his role as team president on June 27.
MLSE president and CEO Keith Pelley said at the time that the organization would begin its search for a new president and that Webster would be considered for the role.
Pelley said on Monday that what convinced him that Webster was the right fit for the expanded role was seeing how well the Raptors’ organization worked at the NBA Summer League in Las Vegas.
“Seeing the culture of the team and the role Bobby has played in getting us here, his leadership style, the rapport with the players and the staff,” said Pelley in a one-on-one phone interview with The Canadian Press. “I think what really came out in the process was his modern vision for the team and how he can specifically relate to players and to staff as an incredibly astute businessman with a deep knowledge of all facets of basketball.”
Webster said that he and Ujiri remain close.
“Great relationship with Masai, no issues there,” said Webster. “We have a long relationship. We’ve been through a lot, so no awkwardness there.”
Pelley sees the new Raptors’ leadership structure as part of MLSE’s ongoing integration of its sports properties that also include the NHL’s Maple Leafs, Major League Soccer’s Toronto FC, and the Canadian Football League’s Argonauts.
He had a recent example of how this new umbrella structure might work, too.
When attacking midfielder Djordje Mihailovic was set to sign with Toronto FC in early August, TFC general manager Jason Herandez told Pelley he wanted one more medical examination of the star player. Instead, Pelley put Hernandez on the phone with Webster.
“I let those two general managers talk together, and the next thing you know, Djordje was seeing the Raptors doctor as a second opinion.” said Pelley. “That’s really the strength and significant advantage that MLSE has, having the four teams, and being able to integrate those teams and operating as one unit, and a group of individuals that are supporting each other in that way is really a competitive advantage that we have.
“So we will continue to integrate the teams, and that extends beyond just front office, and beyond just marketing and game ops. It goes all the way into the players.”
A native of Hawaii, Webster came to the Raptors after seven years at the NBA’s league office, under the leadership of commissioners David Stern and Adam Silver.
Webster worked primarily on the NBA’s collective bargaining agreement and was part of the team that successfully negotiated the 2011 CBA with the National Basketball Players Association. He and his wife Lauren, an entrepreneur and company founder, live in Toronto with their three children.
He said that all of his experiences in the world of basketball helped make this next step of his career possible.
“I just finished my 20th season in the NBA. I think I’ve had a really great opportunity to learn and observe from a lot of leaders,” he said. “I probably view it more as an opportunity for me to see who Bobby is and where we want this team to go.
“Obviously, I’m going to lead with a smile. I’m going lead with a lot of positivity and empower those around me.”
This report by The Canadian Press was first published Aug. 18, 2025.
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