The Best Executives in Toronto Raptors' History Ranked

The Toronto Raptors have had six full-time executives in their history, all of which came together with mixed results.

Toronto Raptors general manager Bobby Webster. | USA TODAY Network via Reuters Connect

Over the course of the last 30-plus years, the Toronto Raptors have been defined by eras in which different people were leading the decision-making in basketball operations.

Some have been successful, while others have struggled. With the offseason in full swing, let's take a look back at the six primary executives and rank them from worst to best.

Executive	Tenure	Record
Isiah Thomas	1994-97	52-123 (.297)
Glen Grunwald	1997-04	226-298 (.431)
Rob Babcock	2004-06	47-78 (.376)
Bryan Colangelo	2006-13	247-337 (.423)
Masai Ujiri	2013-25	545-419 (.565)
Bobby Webster	2025-present	46-36 (.561)

6. Isiah Thomas (1994-97)

Isiah Thomas watches as the Toronto Raptors host the Sacramento Kings. | IMAGN IMAGES via Reuters Connect

Biggest Move: Expansion Draft (1995)

Thomas retired from a legendary 13-year playing career with the Detroit Pistons, where he won two championships in 1989 and 1990 as the team's best player. He immediately went into the front office to help take over the Raptors, who were getting ready to be an expansion team in 1995.

Thomas ranks last on this list because he struggled right out of the gate, but he was also given probably the hardest job out of any of the executives on our list. In his two-plus years with the team, the Raptors won just 52 games while losing 123, resulting in a .297 winning percentage.

5. Rob Babcock (2004-06)

Biggest Move: Trading Vince Carter (2004)

Babcock inherited the team in a very difficult transition period, as Vince Carter was looking to say goodbye and the Raptors' championship window from the early 2000s had come and gone.

Babcock was responsible for trading Carter to the New Jersey Nets in exchange for Alonzo Mourning, Aaron Williams, Eric Williams, and two first-round draft picks. Aaron Williams played in just 37 games for the Raptors, while Eric Williams had 62. Neither was a standout player for the Raptors, which ultimately led to them bottoming out in the NBA standings.

Babcock was fired midway through a second season on the job, winning 47 out of 125 games.

4. Bryan Colangelo (2006-13)

Bryan Colangelo during an introduction press conference. | IMAGN IMAGES via Reuters Connect

Biggest Move: Selecting Andrea Bargnani with No. 1 Pick (2006)

Bryan Colangelo stepped in just over a month after Babcock's departure, but he was able to transform the team. During the offseason, they were granted the number one overall pick. Colangelo's decision to select Andrea Bargnani over others like LaMarcus Aldridge and Rudy Gay has been criticized over the last 20 years, but he still found success making the playoffs in each of his first two seasons on the job.

The Raptors hovered around the .500 mark over the next couple of years, but were ultimately unable to weather the storm that came when Chris Bosh left the team in free agency. Colangelo was tasked with trying to rebuild, but he was unable to see it through. Colangelo stepped down at the end of the 2012-13 season. He went 247-337 in eight seasons with the Raptors.

3. Bobby Webster (2025-present)

Toronto Raptors general manager Bobby Webster looks on as his players warm up before playing the Cleveland Cavaliers. | USA TODAY Sports via Reuters Connect

Biggest Move: Negotiating Reunion Trade for Kawhi Leonard (2026)

While Webster just took over as the head of basketball operations a year ago, he has been with the team since 2013. In 2017, he was named the general manager, but often would work alongside Masai Ujiri. Webster was the general manager when the team won the 2019 championship, but Ujiri is the one accredited with the win.

In Webster's first full season as head of basketball operations, the Raptors went from winning 34 to 46 games, resulting in their first playoff appearance since 2022. Webster is putting the pieces in place to take another step forward in the upcoming season, which gives him the opportunity to move up on this list if these moves pan out.

2. Glen Grunwald (1997-2004)

Indiana Hoosiers forward Glen Grunwald, Steve Risley and Ray Tolbert celebrate. | IMAGN IMAGES via Reuters Connect

Biggest Move: Selecting Vince Carter No. 5 Overall (1999)

Grunwald took over for Thomas after he stepped down as general manager, but he was able to rescue the team after some tough times early on. Grunwald was responsible when the Raptors achieved their first taste of success, making the playoffs in 2000, 2001 and 2002.

The Raptors had a chance to make it further in the playoffs, but a tough seven-game series loss to the Philadelphia 76ers ended their 2001 run a little short.

Grunwald was never able to fully recover from that series loss and the Raptors ultimately reverted back to a lottery team. With just two weeks left in the 2003-04 season, Grunwald was fired, and the team missed the playoffs by three games.

1. Masai Ujiri (2013-25)

Masai Ujiri provides an opening statement during an introductory press conference. | IMAGN IMAGES via Reuters Connect

Biggest Move: Trading for Kawhi Leonard (2018)

The most successful run in Raptors franchise history came with Ujiri leading the way during his tenure as president of basketball operations. The Raptors made the playoffs in seven straight seasons, including a championship in 2019. While the final three years were tough (the Raptors never made it over.500), Ujiri resigned, looking for different opportunities.

He ultimately became the president of basketball operations with the Dallas Mavericks, a position he started back in May. Regardless of what he does with the Mavericks and other teams in the future, he will always be regarded as a Raptors legend and easily deserving of the top spot on this list.

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