'Inspirational' Raptors leader out — how did his reign unravel?

Ujiri — the architect of the franchise’s only NBA title, in 2019, and a once-untouchable executive star — served 13 years with the team. The announcement came Friday, with Maple Leaf Sports & Entertainment CEO Keith Pelley calling the 54-year-old Ujiri “an inspirational leader” who “urged us to believe in this city, and ourselves.”

It’s shocking for Raptors fans — not just because of who he was, but what he means to the franchise. Ujiri brought swagger, vision and credibility to a team that once couldn’t land a marquee superstar. And for years, nearly every move he made worked.

But recently, that magic faded. Toronto hasn’t won a playoff series since 2020. And now, the team’s greatest leader is gone quietly, without the victory lap many expected.

So what happened? And why now?

Let’s explore the rise, dominance and ultimate unraveling of Ujiri’s Raptors.

1. The bold moves that sparked a new era

Ujiri built his legacy by trusting his gut and betting big.

He started fast, flipping power forward Andrea Bargnani and trading small forward Rudy Gay for a crew that became Toronto’s bench mob. That 2013 deal sparked a surprise playoff push and kicked off a seven-year postseason streak.

Ujiri didn’t trade point guard Kyle Lowry when he had the chance. He believed in what he had and that belief changed everything.

2. Drafting and developing the right way

Before Ujiri, Toronto’s draft record was a punchline. He turned it into a pipeline.

He landed point guard Delon Wright (2015), center Jakob Poeltl (2016), power forward Pascal Siakam (2016), small forward OG Anunoby (2017), small forward/power forward Scottie Barnes (2021) and shooting guard Gradey Dick (2023). He also signed undrafted point guard Fred VanVleet.

Many developed with Raptors 905, winning a D-League title in 2017 before stepping into key NBA roles. Development became a franchise trademark.

3. The title that changed everything

2019 was Ujiri’s masterpiece. He traded shooting guard DeMar DeRozan and Poeltl for small forward Kawhi Leonard, fired head coach Dwane Casey, promoted Nick Nurse to HC and brought in center Marc Gasol. Power forward/center Serge Ibaka, acquired earlier, became a key piece.

The result? Canada’s first NBA title — a moment that made Ujiri a superstar executive.

Toronto buzzed with “Kawhi Watch” all summer. Had Leonard stayed, many believe they could’ve repeated.

4. Belief in a fading core

After 2019, Ujiri stayed loyal to Siakam, Anunoby and VanVleet. But the Raptors stalled, missing the playoffs multiple times and falling short in the 2023 play-in.

Ujiri’s belief in internal growth may have cost them key rebuild windows. His faith in “the culture” was admirable, but holding on too long meant missing out on peak trade value and losing VanVleet for nothing.

5. A shift in power

Ujiri’s influence had clearly faded. GM Bobby Webster became more visible. Internal tensions simmered. MLSE’s Rogers-led regime focused more on cost-cutting and short-term results.

With no contract extension and growing uncertainty at the top, Ujiri may have sensed it was time. The franchise he once led with full conviction was headed in a different direction.

6. Legacy lives on

Before Ujiri, the Raptors hadn’t won a playoff series since 2001. Under him, they made eight postseason runs, posted a 545–419 record (fifth best in the NBA since 2014) and won it all.

He is a visionary. A closer. A belief-instiller who changed how Toronto saw itself.

Raptors fans have a right to feel confused, but every reason to be grateful. Masai didn’t just build a contender. He built belief.

That legacy lives on.