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Both men have been with Toronto for years and other long-time staffers will also be sticking around.
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Published Jun 28, 2025 • 5 minute read
Bobby Webster
Toronto Raptors general manager Bobby Webster. Photo by ERNEST DOROSZUK /Toronto Sun files)
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Masai Ujiri is out, but Maple Leaf Sports and Entertainment leadership are handing the Raptors keys to his top lieutenants Bobby Webster and Dan Tolzman.
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Webster and Tolzman are more low key than the dynamic Ujiri, but both have been around the game a long time and helped build the Raptors into a perennial contender and eventually, NBA champions in 2019.
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Here’s more on both:
BOBBY WEBSTER
Webster, a native of Hawaii, spent years working for the NBA’s head office in New York, even helping write a collective bargaining agreement and was seen as a rules and salary cap expert upon his hiring in Toronto in 2013. He joined the NBA in 2006 and was serving as the league’s associate director for salary cap management when he joined the Raptors as Ujiri’s first hire.
“His skill set will beA valuableA in a number of areas, and his experience and knowledge of the CBA and its complexities from a league level will be aA greatA asset to the organization,” Ujiri said at the time.
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The Webster hiring followed an MLSE trend of grabbing highly-regarded up-and-comers from league offices. The Maple Leafs did the same with Brandon Pridham, who is still with the club, and Toronto FC did it with Tim Bezbatchenko who became perhaps the best executive in Major League Soccer and helped TFC become a power until he left for his native Columbus.
When queried by reporters about salary cap or rule minutiae over the years, Ujiri would often quip: “I’ll have to ask Bobby” (if the play was legal).
Webster mostly operated in the background, first as Toronto’s vice president of basketball management and strategy and then assistant general manager in 2016 when Jeff Weltman was promoted to general manager and Ujiri to team president.
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Weltman left the following year to head the Orlando Magic and Webster, at 32, became the NBA’s youngest general manager.
Toronto has won 341 games since Webster became GM, ninth-most in the NBA, including franchise-record 59 and 58 win campaigns, along with the 2019 title. Ujiri and Weltman are amongst the many who long believed Webster would run his own franchise one day.
Webster was seen as a key driver of the franchise-changing Kawhi Leonard deal that sent out DeMar DeRozan, due to a close relationship with San Antonio Spurs general manager Brian Wright dating back to their time together as interns with the Magic.
From before that and until the present day, Webster has done much of the heavy lifting for the Raptors in terms of trade and draft discussions, with Ujiri still of course having been involved and operating as the public face of the franchise.
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Now, Webster will, somewhat reluctantly, given his preference to remain low profile (he once even interviewed for the CIA), step into the spotlight.
Webster lives in Toronto with his wife Lauren and their three children.
Tolzman
Larry Tanenbaum, Chairman Maple Leaf Sports & Entertainment (left) chats with Raptors 905 head coach Jerry Stackhouse (middle) and GM Dan Tolzman as the team celebrates winning the 2017 NBA D-League championship at Celebration Square in Mississauga, Ont. on Friday April 28, 2017. Photo by Ernest Doroszuk /Toronto Sun/Postmedia Network
DAN TOLZMAN
Tolzman’s path to a prominent NBA job was different than Webster’s, but also intriguing.
Born in Tucson, Ariz., Tolzman went to Minnesota to play basketball, but ended up quitting the team at the University of Minnesota-Morris, to join the sports information department. He’d follow that media relations path all the way to the NBA, joining the Denver Nuggets in 2004-05 as an intern. By the time Ujiri was running the Nuggets, Tolzman had been promoted to media relations manager and he then shifted to a role as a scout, which isn’t the most common switch in professional sports.
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Ujiri saw enough out of Tolzman that he brought him with to Toronto as director of scouting when Ujiri replaced Bryan Colangelo as Raptors general manager in 2013.
Tolzman was promoted in the summer of 2015 to director of player personnel and was also named the first general manager of Raptors 905, the club’s developmental squad.
“I’m honoured to have been named the first GM of Raptors 905,” Tolzman said then. “The NBA D-League is all about development, and I look forward to using this opportunity to develop in my career while building and maintaining a competitive roster of young up-and-coming players.
“The benefits of owning a D-League team will be tremendous for the players and staff of the Raptors organization for years to come.”
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Sure enough, Raptors 905 would win a championship and a pair of conference titles in the renamed NBA G League and has served as a pipeline for the big club.
When Webster was elevated and Weltman left in 2017, Tolzman became Raptors assistant general manager and vice president of player personnel, his current roles.
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In general terms, Tolzman has been regarded as the head of Toronto’s scouting department for years now and spearheaded the recruitment and signing of Fred VanVleet as an undrafted free agent and helped the team unearth gems like Pascal Siakam, OG Anunoby and Norman Powell.
He was the chief spokesman for the Raptors when they used to gather the media to chat about draft prospects working out for the team, and he continues to mostly be the draft face of the club leading up to the event each June and right afterward (he talked twice last week, Webster once).
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He has often espoused the take the best player available strategy in drafts, and with Tolzman’s input, the Raptors did just that in taking Collin Murray-Boyles ninth overall, despite a glaring need at centre.
“I think the biggest thing is to not make draft decisions based on your current roster and your current situation,” Tolzman had said years ago. “You keep it in the back of your head. You’ll take it into account when you’re drafting players. But if the most talented guy or the highest guy on your list happens to be in a position where you’re loaded up, you can work something out later.”
While Webster and Tolzman are now at the top of the chain of basketball operations, MLSE president Keith Pelley said the club is searching for a new president (Webster will be in the running for the job) and other long-standing members of the front office (like senior basketball advisor since 2005 Wayne Embry and VP basketball strategy & research Keith Boyarsky, with the club since 2009, amongst others), will also be staying on.
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