The first major domino of the Toronto Raptors’ offseason has fallen.
Bobby Webster, who has served as the Raptors’ general manager since 2017 and has been part of the organization’s front office since 2013. Over the course of his tenure with the Raps he has been promoted to Executive Vice-President and General Manager. Now, most recently, Webster signed a five-year contract extension that will begin in the 2026-27 season.
With Webster’s future locked in, the next move could be keeping another key figure in Toronto long term. According to Michael Grange of Sportsnet, “The next obvious move is an extension for Raptors head coach Darko Rajakovic, who is also entering the final year of his existing contract.”
Grange added that “the timing on that move has yet to be determined, but multiple sources have confirmed it’s in the works.” If indeed an extension does actually get done, it would be hard to argue against it.
The Raptors have improved in each of Rajakovic’s three seasons as head coach. In his first year behind the bench, Toronto finished 25-57 and missed the playoffs. The following season, the team improved to 30-52, but still fell short of postseason contention.
This past year, however, the Raptors took a major step forward, finishing 46-36, earning the fifth seed in the Eastern Conference, and making their first playoff appearance in four years.
The slow start to Rajakovic’s tenure was understandable. When he arrived in Toronto, it was his first full-time NBA head coaching job after spending years as an assistant and briefly serving as interim head coach of the Memphis Grizzlies.
He also joined a team in the midst a major pivot. The Raptors were moving on from the core of their 2019 championship team and eventually dealt both Pascal Siakam and OG Anunoby as the organization shifted toward a rebuild.
Going into 2025, Toronto didn’t even have its own first-round pick and expectations were low. The season was focused more on player development than wins and losses. Well, that all changed this past season.
The Raptors entered the year with a clearer direction, a stronger roster, and much higher expectations. Rajakovic did a strong job establishing an identity for the team and getting players to buy in. Of course, having a healthy Brandon Ingram certainly helped, but Toronto’s improvement went beyond personnel. The team looked more organized and much more competitive than it had in previous years.
Rajakovic’s work did not go unnoticed as he earned recognition around the league. He was selected to coach Team World during All-Star Weekend, became the first European head coach to coach in a postseason game, and even received a third-place vote for Coach of the Year.
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The results speak for themselves. The Raptors have gotten better every season under Rajakovic, and the team is heading in the right direction. He’s shown he can develop young players, navigate difficult circumstances, and help build a winning culture. An extension feels like the natural next step.