A new report reveals Toronto Raptors GM Bobby Webster nearly swapped the NBA for collegiate athletics before securing his extension.
The Toronto Raptors secured their general manager on a multi-year extension on June 8, locking in Bobby Webster as the franchise’s lead decision-maker ahead of one of the most consequential offseasons in years. The move provided stability for a franchise that has been methodically rebuilding since its 2019 championship and confirmed that Webster, now entering his 10th season as general manager, will oversee the next phase of the Raptors’ evolution.
While Webster will continue to man the role he has held for years, he nearly accepted another job outside the NBA, according to Marc Stein of The Stein Line.
“A little over a year ago, league sources say, Hawaii native Bobby Webster was quietly pursued by the University of Hawaii when the Rainbow Warriors needed a new athletic director,” Stein wrote.
This report shows there was more behind the extension than simple recognition for Webster’s work. MLSE was also making sure it kept a top executive who had drawn interest elsewhere.
Stein also revealed new details about the search process that ultimately led to Webster’s promotion.
“Former Raptors coach Dwane Casey, who currently holds an advisory role with Detroit, also featured in Toronto’s search,” Stein reported. “That’s the same title Donnie Nelson held with the Mavericks for nearly 20 years. And Nelson, I’m told, was quietly interviewed by the Raptors last summer after Ujiri’s departure as part of a search they conducted in the buildup to announcing Webster as Ujiri’s full-time successor in August 2025.”
Webster officially assumed control of basketball operations in August 2025 after Masai Ujiri departed for the Dallas Mavericks, where he now serves as president of basketball operations.
Webster’s tenure in Toronto has coincided with the most successful stretch in franchise history. The Raptors have recorded nine playoff appearances, two trips to the Eastern Conference Finals, six Atlantic Division titles, five 50-win seasons, and the 2019 NBA championship.
The next item on Toronto’s agenda appears equally significant. According to Stein, a new contract for head coach Darko Rajakovic is expected in the near future. Sportsnet’s Michael Grange previously identified a Rajakovic extension as “the next obvious move” following Webster’s deal.
Rajakovic is entering the final year of his contract after leading the Raptors back to the playoffs for the first time since 2022. Toronto pushed the Cleveland Cavaliers to seven games in the first round despite playing the entire series without Immanuel Quickley, with Brandon Ingram also missing time.
