The Toronto Raptors’ front office story has been a long one, and it’s been shaped by a handful of executives who each left a very different mark on the franchise.
Some steadied the ship. Some pushed the team forward.
Others inherited impossible situations and got buried by them. With the offseason underway, here’s a look at the six main decision-makers in Raptors history, ranked from worst to best.
Richard Peddie Thomas lands at the bottom. After a legendary 13-year playing career with the Detroit Pistons, where he won championships in 1989 and 1990 as the team’s best player, he moved straight into the front office to help launch the Raptors as an expansion franchise in 1995.
The job was never going to be easy, and Thomas struggled almost immediately. In a little more than two seasons, Toronto went 52-123, a .297 winning percentage.
Rob Babcock followed in a rough stretch of transition, with Vince Carter ready to move on and the Raptors’ early-2000s window already gone. His defining move was sending Carter to the New Jersey Nets for Alonzo Mourning, Aaron Williams, Eric Williams and two first-round picks.
The return never came close to stabilizing the team. Aaron Williams appeared in just 37 games for Toronto, while Eric Williams played 62, and neither made a real impact.
Babcock was dismissed midway through his second season after winning 47 of 125 games.
Bryan Colangelo arrived a little more than a month after Babcock’s exit and quickly gave the franchise some life. Toronto earned the No. 1 pick that summer, and Colangelo used it on Andrea Bargnani over players such as LaMarcus Aldridge and Rudy Gay.
That choice has drawn criticism for years, but Colangelo still put together two straight playoff seasons to begin his run. The Raptors stayed near the .500 line for a while after that, but once Chris Bosh left in free agency, the rebuild became the next challenge.
Colangelo couldn’t finish that job and stepped down after the 2012-13 season, ending an eight-year tenure with a 247-337 record.
Grunwald took over after Thomas stepped aside as general manager and helped pull the franchise through some early turbulence. His run brought the Raptors their first real success, with playoff appearances in 2000, 2001 and 2002.
The high point came with Vince Carter going No. 5 overall in 1999, a move that helped define the era. Toronto had a shot to go deeper in 2001, but a seven-game loss to the Philadelphia 76ers ended that run.
The team never fully recovered from that setback, slipped back into lottery territory, and with two weeks left in the 2003-04 season, Grunwald was fired. Toronto missed the playoffs by three games.
Masai Ujiri oversaw the most successful stretch in Raptors history as president of basketball operations. Under his leadership, the team made the playoffs seven straight seasons and won the 2019 championship.
The final three years were difficult, with Toronto never finishing above .500, and Ujiri eventually resigned in search of other opportunities. He has since become president of basketball operations with the Dallas Mavericks, a role he began in May.
No matter where his career goes from here, he remains a Raptors legend and the clear choice at No. 1 on this list.
Bobby Webster sits in the middle of the ranking for now, but his story is still being written. He has been with the organization since 2013 and became general manager in 2017, often working alongside Ujiri.
Webster was the GM when Toronto won the 2019 title, though Ujiri is the one credited with the championship. In his first full season running basketball operations, Webster helped the Raptors jump from 34 wins to 46 and reach their first playoff appearance since 2022.
He now has a chance to climb higher if the next round of moves pays off.
In Other News...
Raptors Have A Frontcourt Concern Fans Can't Ignore This Season
The Raptors added Trey Jemison III on a two-way contract to give themselves another body in the middle, a move that speaks to how important depth has become behind Jakob Poeltl. Jemison is entering his fourth NBA season and has already logged time on two-way deals with multiple teams, the kind of background that makes him a practical insurance policy rather than a headline-grabber.
Toronto does not need Jemison to be anything more than available and steady, especially with Poeltl carrying the load as the clubs primary big man. But the concern is obvious enough: if the center spot is going to be a recurring issue, the Raptors will need someone who can step in without much notice, and Jemisons presence gives them at least one more option to lean on. [Read more 🡒]
Clippers Still Have Unanswered Kawhi Questions The NBA Never Cleared Up
The NBA has spent nearly a year looking into the Clippers and Kawhi Leonard over allegations that a no-show endorsement arrangement with Aspiration may have skirted the salary cap, and the cloud around the former Raptors star still has a way of reaching back to Toronto. Leonards uncle, Dennis Robertson, also drew scrutiny in 2019 when reports surfaced that he had sought impermissible perks from other teams, though the league never turned up concrete evidence of wrongdoing.
That lingering uncertainty mattered again when the Clippers and Raptors discussed a future Leonard return to Toronto, only for the deal to stall amid the unresolved investigation. For the Raptors, the appeal of revisiting a familiar star came with an obvious risk attached, and until the league finally closes the book on the matter, any Leonard-related path remains a complicated one. [Read more 🡒]