The Masai Ujiri chapter in Toronto has officially come to a close. Toronto Raptors part ways with longtime president Masai Ujiri, marking the end of a successful era.
On Friday, the Toronto Raptors confirmed the departure of their Vice Chairman and President, marking the end of an influential era that spanned more than a decade and brought the franchise its first NBA championship.
Ujiri was approaching the final year of his contract, but Keith Pelley, President and CEO of Maple Leaf Sports & Entertainment (MLSE), shared that the decision to part ways had been made several weeks earlier. made nearly a month earlier.
Speaking to the media at Scotiabank Arena, Pelley said, “Thirteen seasons in a leadership role is a significant tenure in professional sports. Change is a natural part of growth. Considering where our team currently stands and the strong foundation Masai has built, we felt this was the right time to take the next step.”
He continued, “Our roster is complete. All players are under contract, and we’re operating at the luxury tax threshold. We’ve made updates to the front office, with General Manager Bobby Webster continuing in his role, and we’re confident in the steady leadership of our coaching staff under Darko Rajaković.
Pelley also announced that Bobby Webster has signed a contract extension, though specific terms were not shared. He added that Webster will be considered for the President role, along with external candidates, as the search is now underway.
“Bobby Webster is extremely well regarded across the league,” Pelley noted. “His consistent involvement in major trades, strategic moves, and free agency talks has made him a key figure—not just this year but in many past seasons. Still, we are focused on hiring a new President. Whether that turns out to be Bobby or someone new remains to be seen.”
He clarified, “We’re appointing a President, not both a President and a GM. A General Manager is already in position and actively leading within the organization. (…) Our goal is to find a seasoned, dynamic, and proven leader who can take this team to the next level.”
Pelley concluded, “With our team structure solid, player contracts secured, and a stable coaching staff in place, we believe this is the right moment for change and progress.”
Fate already decided
Masai Ujiri was seen at the Toronto Raptors’ training facility, the OVO Athletic Centre, about an hour before the NBA Draft’s first round kicked off on Wednesday. He walked through the lobby and took a moment to greet reporters in the media area.
Even though his exit from the organization had already been decided, Ujiri stayed actively involved in the draft process by his own choice, according to Keith Pelley. During the draft, the Raptors selected Collin Murray-Boyles with the ninth overall pick on Wednesday and Alijah Martin with the 39th pick on Thursday.
On Friday, a video screen outside Scotiabank Arena welcomed the team’s two new players. Inside, Pelley addressed why Ujiri, the man who had just helped draft them, was no longer part of the organization.
“Masai leading this draft says everything about his character,” Pelley shared. “It speaks to the deep trust we’ve always placed in him. He’s always had the team’s best interests at heart—and I know that won’t change.”
Pelley explained that several factors contributed to the decision to move on from Ujiri. With a stable foundation now in place, the organization felt it was the right moment to make a shift.
Appointed by MLSE in January 2024, Pelley said that the board has given him one clear directive: to build championship-caliber teams across all four major sports franchises in Toronto—NBA, NHL, CFL, and MLS.
Under Pelley’s leadership, Ujiri becomes the third high-profile executive to part ways with MLSE, following Brendan Shanahan from the Maple Leafs and Bill Manning, who had roles with both Toronto FC and the Argonauts.
“My job is to ensure all of our teams are performing at a championship level, year in and year out,” Pelley said. “While winning in the CFL might be more manageable, it’s a much tougher task in the NBA, NHL, and MLS. Still, I’m committed to building a winning culture, assembling strong rosters, and doing whatever it takes to succeed.”
He acknowledged that leadership changes are never easy: “Sometimes, making the right decision means making the hard one. Today was one of those moments. But we truly believe this change will help push the Raptors forward—and I will continue doing what’s best for this organization to put us in the best position to win.”
2019 NBA title
In 2019, Masai Ujiri led the Toronto Raptors to their first and only NBA Championship—a historic feat that came as a result of bold and decisive moves. Among them was the blockbuster trade that sent star player DeMar DeRozan to the Spurs in exchange for Kawhi Leonard, as well as the decision to replace Coach Dwane Casey with Nick Nurse.
During Masai Ujiri’s time at the helm, the Raptors consistently reached the playoffs for seven straight seasons, spanning from 2013–14 through 2019–20.
After their championship victory, Kawhi Leonard chose to leave the team in free agency, signing with the LA Clippers. Even after he left, the Raptors remained a strong contender in the COVID-impacted 2019–20 season, wrapping up the regular season with the second-best record in the league. Their campaign ended with a tough Game 7 loss to the Boston Celtics in the second round of the playoffs, which took place in the NBA’s bubble in Orlando, Florida.
Kyle Lowry, a key figure from the Raptors’ golden era, moved to the Miami Heat the next season through a sign-and-trade agreement.. Since then, the Raptors have missed the playoffs Over the past five seasons, the Raptors missed the playoffs four times—including each of the last three—as Ujiri shifted focus toward rebuilding the team during the 2023–24 season.
Longtime point guard Fred VanVleet had already left for the Houston Rockets in free agency prior to the season, and Ujiri later traded forward Pascal Siakam to Indiana and OG Anunoby was traded to New York just ahead of the trade deadline.
After these trades, backup forward Chris Boucher—whose contract is scheduled to end on Monday—stood as the final remaining member of the Raptors’ 2019 championship squad.
The Raptors finished the 2023–24 season with a 25–57 record, a step back from the 30–52 mark they posted the previous year.
Rumors of a rift between Ujiri and Edward Rogers, the Executive Chairman of Rogers Communications and a majority stakeholder in MLSE, surfaced multiple times during Keith Pelley’s press conference. Pelley, however, made it clear on two occasions that the decision to part ways with Ujiri was his own and not one dictated by Rogers.
“I believe all major decisions involve input from every board member,” Pelley said. “Ultimately, it’s the CEO they rely on to guide the team’s vision and overall direction.
“That’s exactly why they brought me in… they wanted someone to oversee all the teams. Yes, everyone has a voice, but ultimately, the final decision was mine—and it was supported by the board.”