Bobby Webster’s Mom got her day started on the right foot.
It was the wee hours of the morning in Hawaii when her son got the news that had been percolating for months, as the Toronto Raptors’ season continued to trend positively but was only made official on Monday morning.
Her son Bobby Webster got a contract extension and title bump from the Raptors, official recognition that, after one year leading the team following the departure of his friend and mentor Masai Ujiri, the longtime general manager would remain on the job for the foreseeable future.
Webster, who has been general manager with the Raptors since 2017 and part of the front office since 2013, will now have the title of executive vice-president and general manager, along with a new five-year deal beginning in 2026-27, per league sources. Webster had one year left on his existing deal.
Arriving at a long-term arrangement was always the most likely outcome when MLSE president and chief executive officer Keith Pelley concluded his executive search last summer by deciding his best way forward was to give Webster a chance to prove himself in the top job.
A strong all-around season for the Raptors was the catalyst for both parties to make a longer-term commitment.
The Raptors improved from 30 wins to 46 wins and fifth place in the Eastern Conference, and punctuated a positive season with a hard-fought first-round playoff series against the Cleveland Cavaliers that went the full seven games, making the decision relatively easy.
“Coming off the past couple years (when the Raptors won 25 and 30 games), you want to feel like you’re building something, and things are going in the right direction,” Webster told Sportsnet. “Even for me personally, for my career, I thought it was important that the team was moving in the right direction … and from a personal standpoint, we all put in so much time, and the coaching staff, over the course of last summer, leading into training camp. We were always very mindful of expectations, but I think we held ourselves to a standard, and so for the team to have a positive season and at least a step in the right direction to me sort of led to all this.”
And it’s nice to get it done, especially for Mom.
“I think you know, Mom always wants an update,” joked Webster, who grew up in Hawaii before attending university in California and getting his first NBA job in his early 20s. So I was able to give her one this morning. She’s six hours behind in Hawaii, but she’ll wake up to some pretty good news.”
In addition to Webster’s extension, longtime assistant general manager and vice-president player personnel Dan Tolzman, vice-president, basketball strategy and research, Keith Boyarsky and Tyla Flexman, vice-president, operations, got extensions, the team announced.
The next obvious move is an extension for Raptors head coach Darko Rajakovic, who is also entering the final year of his existing contract. The timing on that move has yet to be determined, but multiple sources have confirmed it’s in the works.
For Webster, the continuity and chemistry off the court are as important as the progress the Raptors made on the floor this season.
“We don’t make it through the past few years if there’s not a ton of stability, and I think the best part, and everyone can appreciate this, is if you like the people you work with from a professional standpoint, great,” Webster explained. “But if you also like them from a personal standpoint, and you want to come in every day, and travel around the world, and take red eye (flights), and be up late, and get up early in the morning, it matters who you work with on a professional level, but on a personal level it’s just great to have to same crew here.”
But Webster was the one who was making the final decisions for the first time, the executive equivalent of a trusted and respected assistant coach moving one seat over on the bench and suddenly being the person accountable for the endless decisions required in the NBA.
He says he felt aware of it at a couple of different points. The first was when he was the one briefing the MLSE board, including Rogers Communications (MLSE majority owners) executive chair Edward Rogers and chief executive officer Tony Staffieri.
“You’re sharing this vision for the next two to three years, the things we want to focus on, the areas where we’re going to hold ourselves accountable, what you see for the team this year and what you see for the future,” said Webster. “So it requires a ton more, to me, mental preparation. As you can imagine, if you’re meeting with (Edward Rogers) next week, you’re going to think about that for the next week. So in that kind of dynamic, there was newness to the role.”
Webster says he quickly developed a strong working relationship with Pelley and the rest of the MLSE board and made a point of recognizing the “confidence and support” he’s received through his first season at the helm.
The feeling was mutual.
“Bobby is meticulous in everything he does, and the approach he takes to the game is refreshing,” Pelley told Sportsnet. “He has created a great culture here with his relationships with the players and the coaches and around the NBA. His basketball knowledge is elite, and he’s used it to build a team that competed at a high level. The Raptors were a joy to watch come together this year. We’re excited about where his leadership will take us.”
It’s fitting in some ways that Webster’s deal was finalized as the NBA Finals are underway.
As many positives as can be gleaned from the Raptors season that just finished — fifth overall in team defense, all-defence recognition for Scottie Barnes, all-star nods for Barnes and Brandon Ingram, all-rookie honours for Collin Murray-Boyles as well as the progress of second year players Ja’Kobe Walter and Jamal Shead — Webster’s tenure will be judged on how to take the steps from promising and competitive to a team that can contend for a championship.
Watching the Finals, Webster sees some encouraging signs, while acknowledging that teams like the New York Knicks and San Antonio Spurs are at a cut above at the moment.
“It always feels difficult to reach that mountain top, right?” said Webster, who helped the Raptors climb that mountain on their way to the 2019 NBA Championship. “As much as we felt progress in the playoffs, at the same time, we’re still multiple rounds away from getting there.
“But I think what you’re seeing in these high-level games is what we’re striving for. So, whether it’s defence and physicality or quick decision making and ball movement on the offensive end, I think those are sort of the principles that we started to install this year, but I think the skeleton of what we’re preaching works at the highest level, and now it’s on us, and the players, and coaches, and medical staff to get us there.
“Is that internal growth? Is that us looking for opportunities to — not necessarily speed things up — but to start to push our chips into the middle?
“So we’re studying it, but you also have to be true to who you are.”