Webster inherits Raptors’ top job without getting new title

TORONTO – After an expansive two-month search to find a replacement for Masai Ujiri, it turns out Maple Leaf Sports & Entertainment didn’t have to look very far.

The conglomerate, which owns the Toronto Raptors and many of the city’s other sports and entertainment properties, cast a wide net once Ujiri was relieved of his duties in late June.

Multiple external candidates were interviewed, including Indiana Pacers general manager Chad Buchanan, Chicago Bulls GM and Canadian executive Marc Eversley, and former Raptors head coach turned Detroit Pistons executive Dwane Casey, who met with MLSE on at least three occasions last month, according to league sources. They also kicked the tires on Pacers president Kevin Pritchard, among others.

Ultimately, they decided to stay in-house. Bobby Webster, the club’s long-time GM and Ujiri’s top lieutenant, will inherit his predecessor’s job atop the Raptors front office and head up basketball operations.

With the new gig, the 40-year-old native of Hawaii gets a contract extension and a nice raise, as well as an increase in responsibility and pressure. The one thing it doesn’t come with is a fancy new title. At least for the time being, Webster will lead the team from the general manager position, as they’ve opted against appointing a president.

“When we weighed the many considerations, including roster construction, team culture and competitive landscape, it made perfect sense to officially hand the team to Bobby and give him the time and support to allow his plan to develop,” MLSE president and CEO Keith Pelley said in a press release on Monday afternoon.

“After spending time together this summer in Las Vegas, I was very impressed by Bobby’s leadership style, his rapport with the players and staff, his reputation with his peers across the league and – especially and importantly – his vision for the Raptors. This team is his, now, to lead, and I know we all look forward to what comes next.”

This arrangement isn’t entirely unusual. Nearly half of the league’s 30 clubs are currently operating without a dedicated team president, including the reigning champion Oklahoma City Thunder, who have longtime GM (and executive vice president) Sam Presti reporting directly to ownership.

In the 30-year history of the Raptors, only two people have held the title of team president without also serving as the GM: Richard Peddie from 1996 to 1998 and Ujiri from 2016 until June (Bryan Colangelo served as both from 2006 to 2013).

It's a solution that was floated here last month, shortly after MLSE began vetting a list of recommended candidates from the Los Angeles-based CAA Executive Search firm. The initial plan to replace Ujiri and hire another president caught several insiders by surprise, given MLSE essentially did away with the position on the soccer and hockey sides after moving on from Toronto FC's Bill Manning and the Toronto Maple Leafs' Brendan Shanahan this past year.

The sense, then, was that they weren’t convinced Webster was ready for the job. If they didn’t want to fully commit to Webster, but weren’t enamoured with any of the external candidates who fit their modest budget (and that part is key), would they be willing to call an audible and leave the position open?

Doing so allows them to continue grooming Webster and assistant general manager Dan Tolzman, see how they perform in their elevated roles and how the team they helped build fares next season, while also maintaining the flexibility to pivot if they don’t like how it looks. After signing a short-term contract extension earlier this summer, the promotion gives Webster a bit more security. Terms of his new deal weren’t disclosed, but it’s safe to assume he will not match Ujiri’s $15 million annual base salary. 

It’s a vote of confidence in the young executive and should help alleviate some of the nervous energy around the organization, but there’s a reason why they made sure to etch the new front office hierarchy in pencil rather than using permanent ink.

Things could change in hurry if this team, led by head coach Darko Rajakovic and an expensive core of Scottie Barnes, Brandon Ingram and Immanuel Quickley, doesn’t take a meaningful step forward this season. For now, this leadership group can breathe a sigh of relief, but none of them should feel especially safe.

“The title, to me, isn’t as important as the responsibilities,” Webster said. “I’m really thankful for this opportunity. I’ll make the most of it and [the title is] not something that concerns me.”

According to multiple sources, some of the external candidates that were interviewed for the president position pushed back on recent roster decisions made by Ujiri and his front office. One went as far as calling the trade to acquire Ingram in February a “desperate Hail Mary.” They questioned the team’s post-championship leadership and internal development and pointed out its salary crunch – going into the new season with the league’s eighth-highest payroll despite winning 55 games over the past two years and having the 21st-highest projected win total for the 2025-26 campaign, per FanDuel.

The fact that MLSE opted for status quo, instead of cleaning house and bringing in someone new, tells us a couple things. Firstly, it reiterates what we already knew: the Ujiri firing had more to do with money than vision. It also says that this new-look ownership group, led by Pelley and a Rogers-controlled board, still believes in the plan.

If that’s the case, the younger and less expensive Webster is the logical choice to pick up where Ujiri left off. After meeting with members of the MLSE board over the past month and getting to know Pelley better in Vegas over Summer League, and vice versa, his new deal was finalized over the weekend.

From a basketball standpoint, it’s hard to imagine him taking over and completely overhauling the roster. He may not have been in lockstep with every decision that his former boss made, but they clearly share a vision.

Webster was one of Ujiri’s first hires back in 2013, then as the vice president of basketball management and strategy. He’s had his hands in every move the team has made over the last decade-plus, including playing a key role in the Kawhi Leonard trade that led to Toronto’s 2019 championship, but he didn’t have final say or full autonomy on any of them. This is his chance to prove that he’s more than just Ujiri’s right-hand man, an expert salary cap manager, or front office wunderkind. 

“I grew up playing basketball as a small kid and to have it lead all the way here is unbelievable,” Webster said. “In many ways, I’m ahead of my time. I finished university at 20, GM at 30, we win a title at 32, I’m here in this position at 40. So, a lot of it is leading people that are older than you, leading people that are often more experienced. Now I’m transitioning to be that person with more experience, but I am still sort of relatable and young. Generationally, I’m not going to be this authoritarian corner office type.”

Having spent nearly half his life in the NBA, Webster isn’t lacking for relevant experience. He hasn’t just learned from Ujiri, but also MLSE chairman Larry Tanenbaum, former Raptors GM and current Orlando Magic president Jeff Weltman, the legendary Wayne Embry and NBA commissioners Adam Silver and the late David Stern at the league office, where he helped write the old CBA. He understands the market and what makes it unique. He’s savvy, well regarded, and has a good eye for talent. If the Raptors weren’t willing to give him this opportunity, somebody else would have in short order.

He's not Ujiri, but he doesn’t have to be to have success in this role or eventually earn the title of president. He doesn’t need to win the press conference to the degree that Ujiri did if he finds a way to win where it matters most. That’s where he can really make a name for himself.

“I view it as an opportunity for me to [show] who Bobby is and where we want this team to go,” he said. “You know my personality. Obviously, I’m going to lead with a smile. I’m going to lead with a lot of positivity, empower those around me.”

“Masai was incredibly inspirational and motivational… But I’m going to be Bobby and I think people know who that is.”