TORONTO \u2013 After an expansive two-month search to find a replacement for Masai Ujiri, it turns out Maple Leaf Sports & Entertainment didn\u2019t have to look very far.<\/p>\n
The conglomerate, which owns the Toronto Raptors<\/a> and many of the city\u2019s other sports and entertainment properties, cast a wide net once Ujiri was relieved of his duties in late June.<\/p>\n Multiple external candidates were interviewed, including Indiana Pacers<\/a> general manager Chad Buchanan, Chicago Bulls<\/a> GM and Canadian executive Marc Eversley, and former Raptors head coach turned Detroit Pistons<\/a> 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.<\/p>\n Ultimately, they decided to stay in-house. Bobby Webster, the club\u2019s long-time GM and Ujiri\u2019s top lieutenant, will inherit his predecessor\u2019s job atop the Raptors front office and head up basketball operations.<\/p>\n 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\u2019t 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\u2019ve opted against appointing a president.<\/p>\n \u201cWhen 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,\u201d MLSE president and CEO Keith Pelley said in a press release\u00a0on Monday afternoon.<\/p>\n \u201cAfter spending time together this summer in Las Vegas, I was very impressed by Bobby\u2019s leadership style, his rapport with the players and staff, his reputation with his peers across the league and \u2013 especially and importantly \u2013 his vision for the Raptors. This team is his, now, to lead, and I know we all look forward to what comes next.\u201d<\/p>\n This arrangement isn\u2019t entirely unusual. Nearly half of the league\u2019s 30 clubs are currently operating without a dedicated team president, including the reigning champion Oklahoma City Thunder<\/a>, who have longtime GM (and executive vice president) Sam Presti reporting directly to ownership.<\/p>\n 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).<\/p>\n It’s a solution that was floated\u00a0here<\/a> 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<\/a>‘ Brendan Shanahan this past year.<\/p>\n The sense, then, was that they weren\u2019t convinced Webster was ready for the job. If they didn\u2019t want to fully commit to Webster, but weren\u2019t 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?<\/p>\n 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\u2019t 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\u2019t disclosed, but it\u2019s safe to assume he will not match Ujiri\u2019s $15 million annual base salary.\u00a0<\/p>\n It\u2019s a vote of confidence in the young executive and should help alleviate some of the nervous energy around the organization, but there\u2019s a reason why they made sure to etch the new front office hierarchy in pencil rather than using permanent ink.<\/p>\n Things could change in hurry if this team, led by head coach Darko Rajakovic and an expensive core of Scottie Barnes<\/a>, Brandon Ingram<\/a> and Immanuel Quickley<\/a>, doesn\u2019t 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.<\/p>\n \u201cThe title, to me, isn\u2019t as important as the responsibilities,\u201d Webster said. \u201cI\u2019m really thankful for this opportunity. I\u2019ll make the most of it and [the title is] not something that concerns me.\u201d<\/p>\n 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> a \u201cdesperate Hail Mary.\u201d They questioned the team\u2019s post-championship leadership and internal development and pointed out its salary crunch \u2013 going into the new season with the league\u2019s 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.<\/p>\n 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.<\/p>\n If that\u2019s 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.<\/p>\n From a basketball standpoint, it\u2019s 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.<\/p>\n Webster was one of Ujiri\u2019s first hires back in 2013, then as the vice president of basketball management and strategy. He\u2019s had his hands in every move the team has made over the last decade-plus, including playing a key role in the Kawhi Leonard<\/a> trade that led to Toronto\u2019s 2019 championship, but he didn\u2019t have final say or full autonomy on any of them. This is his chance to prove that he\u2019s more than just Ujiri\u2019s right-hand man, an expert salary cap manager, or front office wunderkind.\u00a0<\/p>\n \u201cI grew up playing basketball as a small kid and to have it lead all the way here is unbelievable,\u201d Webster said. \u201cIn many ways, I\u2019m ahead of my time. I finished university at 20, GM at 30, we win a title at 32, I\u2019m 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\u2019m transitioning to be that person with more experience, but I am still sort of relatable and young. Generationally, I\u2019m not going to be this authoritarian corner office type.\u201d<\/p>\n