Opinion: MLSE CEO’s vision for the Toronto Raptors feels very corporate instead of inspiring

The Raptors’ new blueprint looks suspiciously like a Maple Leafs rerun — and that should terrify everyone.

Keith Pelley stepped to the mic a few weeks ago and tried to thread the needle between gratitude and ruthlessness, praising Masai Ujiri’s championship legacy and culture-building magic before firmly declaring that the franchise had reached its inflection point. With the roster locked in, the front office extended, and a recent coaching staff in place, Pelley framed Masai’s exit as a calculated move to keep the Raptors’ rebuild on track, stressing that this was his decision, not Ed Rogers pulling strings behind the curtain. He vowed to find a bold, “business-minded” president to steer the ship, while Bobby Webster would get a fair shot at the role.

That press conference felt like Pelley took the podium with a corporate polish but left Raptors fans spinning, dropping the kind of bland executive speak that felt more like a shareholder briefing than a rallying cry for a confused and worried fan base. While he saluted Masai Ujiri’s championship legacy and community impact, he pivoted to vague buzzwords about “stability” and “timing” without really explaining why a proven architect had to go in the middle of a rebuild he helped design.

The contradictions stacked up — praising Masai’s draft genius while cutting him loose weeks later — and his repeated insistence that this was his call, not Ed Rogers’, only fueled more side-eye from a skeptical crowd. In the end, Pelley’s press conference left fans grasping for a vision beyond business suits and boardroom strategy, wondering if the Raptors’ identity had just been traded for a balance sheet.

Under Masai Ujiri, the Toronto Raptors enjoyed their best era — on the floor, he rebuilt the culture along with former Raptors coach Dwane Casey, built the team identity and brand (#WeTheNorth), turned the team into a perennial playoff contender, oversaw one of the NBA’s best developmental systems that unearthed the likes of Fred VanVleet and Pascal Siakam, pulled the trigger on one of the ballsiest trades in the NBA in Kawhi Leonard, ultimately leading to the 2019 championship, managed the toughest sports situation during Covid (Tampa), etc. Essentially, Ujiri transformed the Raptors from a middling, forgotten franchise north of the border into an NBA champion and an international brand, leaving a legacy of culture, development, diversity, winning, and a reputable organization.

Vague Excuses About the Move

It’s not surprising to see Masai Ujiri go, but if anything, the expectations were that he would have gone out on his terms. Whenever a company changes ownership or undergoes a major shift in controlling influence, new owners often reevaluate the leadership, prioritize/put their people in charge, and control costs. This includes a deeper look at the executives’ compensation, budgets, and how they justify their performance metrics.

There are many reasons to let Ujiri go. If you look at how things are done in the corporate world, perhaps Ed Rogers felt he needed his “own guy” to run the team. Ujiri symbolizes the old regime, and the new ownership might see him as either too independent or not fully aligned with their priorities. There’s also the aspect of performance.

“I can’t say it any more times than there are many factors that came into this decision, and the timing was right to make a change.” - Keith Pelley, MLSE CEO

It hasn’t been peaches and cream since the Tampa season. The post-championship retool was somewhat fun but a disaster, barely held by the Kyle Lowry band-aid. Since the GROAT left, it’s been mostly frustrations, with Ujiri calling out the team’s culture of selfishness, coach Nick Nurse’s firing, the way the team handled Pascal Siakam’s exit, losing seasons, and the inability to build a coherent team that the fanbase can get behind.

I doubt this firing is purely about Ed Rogers’ rift with Ujiri. Maybe that’s at the root of it all, but suffice to say, once Rogers had effective control, they likely acted like what a new owner would in a corporate acquisition: evaluate Ujiri’s performance, consider his compensation (rumoured to be $15m), and the franchise’s current direction.

Sadly, Pelley’s messaging fell short of explaining the decision—his value excuses like “this was the time to make the change” and “change is inevitable and sometimes getting in front of it is necessary” are, in Winston Churchill’s own words since he invoked him, “Terminological inexactitude.”

Organizational Reset Within MLSE

Over two years ago, I wrote that the Toronto Raptors might be due for an organizational reset, not explicitly calling for heads to roll. Still, Masai Ujiri came out with guns blazing about how the culture has been bad and needs to reset. “Culture Reset” was the buzzword then, but it felt like the team needed more than that. It felt like everything got stale — the used-to-be model organization seemed to be lagging behind good teams in terms of roster construction, developmental system and pipeline, coaching, etc., essentially calling for the need to reassess the organization’s core personnel, coaching philosophy, developmental strategy, and cultural identity to get back to prominence.

Whether it’s Bobby Webster or the “new guy,” Ujiri’s replacement would need to approach this situation with the organization’s mindset, which requires an Organizational Reset.

Should MLSE decide to hire a new face to replace Ujiri as the team’s President of Basketball Operations (POBO), we should expect some shakeup. Sure, Webster and Dan Tolzman have an extension. According to SportsNet’s Michael Grange, the extensions run through the end of the 2026-27 season. While they might be on board for the coming season, we heard no guarantee from Pelley that they are here to stay in the future. Also, as with new regimes, the new POBO will likely want to assemble his team sooner or later. Usually, the last year of the contract is a nice “separation package” that companies (and in this case, sports teams) would give.

Up next should be the coaching staff. Sure, coach Darko Rajakovic’s done a magnificent job learning on the job. He has shown that he can install a good locker room culture and developmental system and, at times, display competent in-game coaching. However, given the team’s direction and timeline and what the POBO wants to achieve, they might need to evaluate whether this is the right coaching staff moving forward.

Then we have the roster and talent management. Could a roster overhaul be in play? The ledger, not just the talent, must also be factored in. Is player X worth the salary or the upcoming extension? Does the team have enough support to maximize the talent and value of its players, especially its young talent?

Also, what if Webster gets the job?

Bob the Builder?

During the presser, Keith Pelley mentioned that Bobby Webster (along with Assistant GM Dan Tolzman) got extended and that he’s a candidate for the vacated position. As discussed above, SportsNet’s Michael Grange got the intel that it’s a one-year extension. Webster (and Tolzman) should have immunity at least for the coming year, as Pelley mentioned, “Whether that’s Bobby (Ujiri’s replacement) is to be determined. But we’re not hiring a president and a general manager. We’re hiring a president, and we will have a general manager.”

While those lines may sound encouraging, they only guarantee Webster’s job this coming season if he doesn’t land the job. If MLSE brings in a new face, this season will be a transition year. It’s a year for the new executive to evaluate the entire basketball operations, including the team. Depending on which direction the ownership wants to go, they will need Webster’s cap expertise to navigate the next few months.

We’re a few days into the free agency — a lean one where most teams don’t have any cap space, and the free agent crop is mostly B-listers. Webster made a “splash” with his first transaction post-Ujiri: re-upping Garrett Temple. He then flexed with a Jakob Poeltl extension at a good value and a great deep end of the bench pickup in Sandro Mamukelashvili.

However, with the lack of a public mandate or strong endorsement from Pelley, the fanbase entered the free agency period trying to guess what activities we’ll see — whether Webster is advised not to make drastic changes until the “POBO” is sorted out, or if he’s got the blessings of the management to make big moves as part of his audition for the job. So far, the moves fall into the former, as even though the Poeltl extension may outlive Webster’s Raptors tenure, it’s a manageable contract that won’t hamper the team in the future.

This free agency cycle could allow Webster to show he fits the job if the ownership trusts him to make big moves outside of trading Scottie Barnes. Just because the roster is full doesn’t mean it is set. If given the chance, Webster could operate between further reshaping the team’s roster talent and improving the accounting books in the process, making the salary cap situation much more manageable next season. He knows the team inside and out, so there’s no theory or future planning in a PowerPoint presentation that will get him the job as is.

Outside of that option, it’s tough sledding for Webster. Does the ownership see him as an “Ujiri-continuation,” which might work against his favour? It’s probably why we’re seeing some leaks, courtesy of SportsNet’s Michael Grange, showing Webster flexing his muscles (I suggest you give it a read). This is demonstrated by Webster rallying the troops around the same time as Pelley’s presser, painting Webster as a leader more focused on the team than his relationship with his outgoing boss. Another is how Webster and Ujiri saw Pascal Siakam’s contract extension situation.

What Does Ed Want?

The Toronto Raptors’ organization’s fall from grace after achieving its peak when it won the championship in 2019 is a curious one. While it’s easy to pile on Masai Ujiri, we may want to look past just Ujiri’s fingerprints. While Ujiri publicly admitted at the end of the 2022-23 season that the franchise needed a rebuild, what transpired next felt more like every time Precious Achiuwa pushed the ball in transition, rather than a proper teardown rebuild. Could part of Ujiri’s decision-making have been affected by the MLSE’s big-picture priorities, and Ed Rogers’ growing influence behind the scenes?

Let’s be real: the corporate suits in the board room don’t lose sleep over Gradey Dick not getting developmental minutes, or having a roster that complements Scottie Barnes’ skill set — they worry about the butts in seats, ticket renewals, and yes, TV ratings that keep the sponsorship going. It’s no secret that ticket sales and broadcast ratings have gradually sagged since the Raptors’ 2019 chip run and the defiant “#WeTheChamps” pre-COVID run. Heck, even the Lowry/DeRozan #WeTheNorth runs got strong ticket attendance, which often led to sold-out games. Despite decent ticket sales these past two seasons, there have been many games where the visible crowd looked like the Miami Heat’s crowd after the 1st period — except, it was for the whole game. Worse, teams keep their star players south of the border, making it worse for the fanbase’s viewing experience, live, or watching from the tube, considering how expensive it is to watch a Raptors game live, or even watch the game digitally.

When your sponsorship partners and affiliates are used to playoff buzz (and getting a taste of Finals-level engagement), even a short dip feels like a stomach punch to the brand. When you’re losing your viewership due to a bad product on the floor, often a byproduct of a “rebuilding process,” it’s hurting everyone’s pockets—from the organization to the ownership, sponsors, affiliates, and indirect businesses that depend on the team’s success. It felt like Ujiri tried to thread an impossible needle. Instead of fully committing to a multi-year roster renovation, he tried to hedge and “rebuild” from the middle and failed to the point where things blew up on his face.

It feels like there was an unspoken corporate message: rebuild — sure, but don’t tank. Now that Rogers has a controlling stake in MLSE, MLSE’s revenue streams depend on fans staying plugged in. While Pelley did say that the new Team President said that “worrying about commercials or tickets is not going to be a priority,” it’s still part of the equation, as it’s business, after all. A miserable 18-25-win season can send sponsorship money into hibernation, not a fun periodical financial board meeting that would have happened for a year or two, if not more. That said, it feels like the ownership will not greenlight a ground-zero teardown with empty seats and silent turnstiles.

“... and we just seize the opportunity at this particular time with where we are in the evolution of the rebuild to, to make a move that hopefully now will build on what is a real young aggressive team that Bobby and Masai has built and a foundation that he has built. And so somebody is coming in, in the midst of a rebuild, and we’ll hopefully expedite that and bring us to a new level quickly.” - Keith Pelley, MLSE CEO

So, what does MLSE really want? Pelley said their number one priority is finding the right person to get the Raptors back into contending and winning championships. That doesn’t sound like a team that must take a step back for a season or two. Pelley mentioned “Championship” several times during his presser, including when asked about his legacy. The way the team quickly pivoted after the “rebuilding” proclamation two years ago, and what Pelley said during his presser, it sounds like MLSE wants this team back in the thick of playoff action as soon as possible, which would be great for their business. Is that the right choice? Does the ownership believe that this current core of Scottie Barnes and Brandon Ingram can get it done, or are they looking for someone who can restructure this roster, like how fast Japan fixes its sinkholes? Is that why the Raptors are in “Talent Acquisition Mode,” aka stacking trade chips?

It’s clear that Masai Ujiri’s pay stub and independent leadership didn’t mesh with Rogers’ lean, top-down corporate norm. Nevertheless, by removing Ujiri, MLSE will get a new executive more aligned with Rogers’ business style, directly accountable to the ownership, and allowing Rogers to formally consolidate power within MLSE’s Raptors wing.

However, Ujiri’s replacement will have their hands full — it doesn’t look like MLSE’s corporate culture is built to stomach a long, painful rebuild. While there is not one surefire way of restructuring a roster, the ownership has to be aware that taking shortcuts in building a championship contender, while potentially profitable, often doesn’t pan out. Unless the ownership is satisfied with the Toronto Maple Leafs’ model — where the team is competitive enough and profitable for decades — regardless of whether they win a ‘chip or not. In Pelley’s own words, he’s looking for a “a strong, prominent businessman with an in-depth background in basketball operations.”