Search for new Raptors president is underway, but best candidate could be in-house

TORONTO – The Toronto Raptors are doing their best to convey business as usual, even if it’s anything but.

For the third straight summer, the team is working out of a hotel ballroom-turned-state-of-the-art basketball facility in Las Vegas, where they’re approaching the halfway point of a tournament they have a good shot at winning.

Their attendance record is nearly perfect. Toronto’s loaded Summer League roster has been practicing on one side of the gym while a full contingent of its veteran players train on the other. The team website lists 80 people on its staff – from front-office personnel to the coaches, trainers, and chefs – and more than 90 per cent of them made the trip in the hopes of showing face, proving their worth, and sussing out their place in whatever comes next.

The elephant in the room is the one person who’s no longer in the room: the recently dismissed team president, Masai Ujiri. Nobody is talking about their former boss or even speaking his name aloud. Ask somebody about him, on or off the record, and you’ll get a scripted response, something along the lines of: "He did great things and will be missed, but life goes on."

Requests to make general manager Bobby Webster or other members of the front office available to the media have been declined, even for stories unrelated to Ujiri, and the sense is that the code of silence is a directive coming from the very top. The nervous energy is palpable.

Most people in the organization knew that change was inevitable, with Ujiri going into the final year of his contract and Rogers taking control of Maple Leaf Sports & Entertainment. But the timing – the day after the draft – hit them hard and, two weeks later, the shock hasn’t worn off.

On one hand, in the highly competitive world of professional sports, it’s not unusual to have doubts about one’s job security. But, even by NBA standards, to have this many people looking over their shoulder at once is notable. And given that the longtime face of the franchise was just let go and the new-look ownership group has promised more change, it’s entirely justifiable.

“Everybody is scared,” said one team source, who asked to remain anonymous. “The closer you are to the top, the more you feel it.”

Fortunately, the players are far enough removed that it shouldn’t affect the on-court product in any meaningful way. If there’s anybody who should be feeling the pressure it’s Ujiri’s top lieutenant, the generally calm, cool, and collected Webster, who has been thrust into an unfamiliar position.

The Hawaiian-born executive has worn many hats during his two decades in the NBA, which accounts for half of his life. He’s been the team’s pseudo-accountant, using the expertise he gained working in the league office (where he helped create the old CBA) to manage the salary cap. He’s been a key negotiator in significant deals, like the one that brought Kawhi Leonard to Toronto and ultimately led the franchise to its first championship. He’s scouted talent and been a crucial liaison.

The one thing he hasn’t done is own the spotlight. Humble and unassuming by nature, Webster has always seemed comfortable operating in Ujiri’s shadow, but that doesn’t mean that he’s incapable or unwilling to step out of it. At his press conference late last month, MLSE CEO Keith Pelley indicated that Webster would be considered for the vacant president position, and by all accounts, the 41-year-old is very interested.

But to say that it’s his job to lose may be a stretch. Pelley seemed to give off the impression that their preference was to bring in somebody new and keep Webster in the GM role for the time being, and that’s the sense that league insiders have gotten, as well.

The search for the next Raptors president is officially underway. MLSE has enlisted the services of Los Angeles-based CAA Executive Search and, according to league sources, the firm submitted a list of recommended candidates to the board last week. They’re believed to be in the vetting stage. Pelley wouldn’t put a hard timeline on the process, but it’s fair to say they would like to have somebody in place well before training camp opens at the end of September.

There aren’t many names floating around at the moment, and the ones that are out there appear to be pure speculation. Bob Myers? There’s no indication that the former Warriors exec would leave his cushy broadcasting gig at ESPN to get back into the front office and he is almost certainly too expensive for an organization that appears to be on a cost-cutting mission. A few plugged-in folks have wondered if they would follow a recent league trend and hire a current or former player agent, in the mould of the Los Angeles Lakers (Rob Pelinka), Utah Jazz (Justin Zanik) or the CAA-controlled New York Knicks (Leon Rose).

As if the situation wasn’t precarious enough already, imagine asking Webster to report to somebody with less relevant experience, who beat him out for the job that he wanted and felt that he earned. He was recently given a contract extension, along with the other prominent members of his leadership team, but according to sources, those deals run through the 2026-27 season. Hardly a long-term commitment or something that would preclude a new president from cleaning house and bringing in their own people.

But letting Webster go or, worse, forcing him out the door would be a mistake. He checks off a lot of crucial boxes that should be considered prerequisites for Toronto. He’s savvy and knows how to manage the cap, which has never been more important than it is with the complexities of the new CBA. He’s got an eye for talent. He understands the market and what makes it unique. He’s learned from one of the best to ever do it. All of that can also be said for his second-in-command, assistant general manager Dan Tolzman. Oh, and unlike Ujiri, whose $15 million annual salary (plus bonuses and raises) was deemed too rich for MLSE’s blood, those guys are more affordable. 

What would a Webster-led front office look like? We don’t know. Nobody does. His fingerprints are all over just about every move the Raptors have made since Ujiri hired him in 2013 and then promoted him to GM back in 2017, but he hasn’t had full autonomy or final say on any of them. While Ujiri often deferred to, empowered and championed his people, there was never any doubt who was in charge.

Webster isn’t Ujiri, but that may end up being more of a feature than a bug. He doesn’t bring that same larger-than-life personality or gravitas, qualities that Toronto fans have generally looked for in their sports executives, but he’s as down to earth as it gets in this business and at that position. He has a more understated leadership style and a different way of communicating. While some rival execs were intimidated and occasionally put off by Ujiri, it’s hard to imagine anybody saying, "We won’t deal with Webster." He’s a bit of a chameleon in that he can dress down and have casual conversations with players or team staff while also fitting in with and commanding respect from his front-office colleagues and peers. The biggest question is whether he’ll be able to hold an audience in the MLSE boardroom – an arena in which Ujiri always felt comfortable – and sell the suits on a trade, signing or, crucially, himself.

As for what a Webster team might look like on the court, many will assume he’ll simply adopt Ujiri’s vision. Like his predecessor, he’s known to value long, versatile, defensive-minded players, as his ninth overall selection in last month’s draft – big man Collin Murray-Boyles – would indicate.

“[With] the positionless-ness of the NBA now, I don’t think you can have too many of these big, two-way wings,” Webster said after the Raptors made Scottie Barnes the fourth-overall pick in 2021. “We see it as, let’s have all five guys look like him and OG [Anunoby] and Pascal [Siakam].”

However, the idea that he’s simply a Ujiri disciple is a misconception. Just because two people work closely together over a long period of time doesn’t mean they share the same tendencies. A recent example: Nick Nurse worked under Dwane Casey in Toronto for five seasons before the former replaced the latter as head coach and, as it turned out, couldn’t have been more different in approach, philosophy, or personality – for better and for worse.

According to multiple sources, Ujiri was the “driving force” behind the Brandon Ingram deal at last February’s trade deadline, while others in the room were less convinced about the fit and the timing. To just assume that Webster would pick up where Ujiri left off might be misguided. They could use a fresh perspective after missing the playoffs in four of the past five seasons, but they don’t necessarily need to look outside of the organization for that. The grass isn’t always greener.

In Webster, they’ve got a well-regarded, highly sought-after young executive. If they’re not convinced or ready to commit to him in the president role, here’s a solution that doesn’t alienate or risk losing him: leave the position vacant, at least for now. It was mildly surprising when MLSE announced that it would be hiring a successor for Ujiri, especially after the company parted ways with Bill Manning and Brendan Shanahan on the soccer/football and hockey sides and opted against replacing them.

It would be odd to hire a search firm and commit to finding a new president only to walk it back and delay the process, but that might be the best course of action. As Pelley correctly pointed out in his press conference, there’s no definitive blueprint on how to structure a front office in pro sports. 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 general manager (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 last month (Bryan Colangelo served as both from 2006 to 2013).

Theoretically, they could have Webster run basketball operations from the GM position and see how he fares as the primary decision-maker before making a long-term call. If it works and the team has a successful season, they could elevate him (and Tolzman) next summer. If it doesn’t, they could pivot but they’ll have done their due diligence and would have an easier time justifying the decision to bring in somebody new.

Just a thought, but we’ll see. In the meantime, MLSE needs to hope that the uncertainty it's created lights a fire under this organization and its many employees for as long as it takes to figure out where it goes from here. It might work. These are highly competitive and prideful people who are now officially on notice; they’re performing for their jobs. But leaving them in limbo for an indefinite period isn’t a sustainable strategy, nor is it a humane one. At some point, something’s got to give. 

For now, it’s business as usual (or something like that).