Maple Leaf Sports and Entertainment has parted ways with Toronto Raptors president and vice chairman Masai Ujiri, the team announced Friday. Ujiri, who led the Raptors to the 2019 NBA championship and pulled off one of the boldest trades in modern NBA history for Kawhi Leonard, had one year remaining on his contract.

In a statement, the team said it had agreed to extensions with multiple members of the front office, including Bobby Webster, its long-time general manager. MLSE also said it will look for an executive to lead the Raptors, in a search led by CAA Executive Search.

“During his 13 seasons with the Raptors, Masai has helped transform the organization on the court and has been an inspirational leader off it,” MLSE president and CEO Keith Pelley said in a statement. “He brought an NBA championship to Toronto and urged us to believe in this city, and ourselves. We are grateful for all he has done and wish him and his family the very best.”

Ujiri’s future with the Raptors has been uncertain several times over his 12-year tenure as president, but especially since last September, when Rogers Communications announced it had bought a 37.5 percent share of MLSE from its telecommunications rival Bell, giving it a controlling share of the company. When MLSE and Ujiri agreed to his new five-year contract in 2021, Edward Rodgers, now MLSE’s executive chairman of the board, was not as enthusiastic about giving Ujiri top-of-the-line money to continue.

Ujiri had said his relationship with Rogers was fine several times since then. But earlier this year, after MLSE let Toronto Maple Leafs president Brendan Shanahan’s contract expire after a decade in charge of the hockey team, it was clear that changes could be coming.

Ujiri was in charge of the Raptors even longer than Shanahan was in charge of the Maple Leafs, and will go down as a Toronto sports legend. Former MLSE CEO Tim Leiweke hired Ujiri as president of basketball operations in 2013, as he was coming off winning executive of the year as general manager of the Denver Nuggets. Quickly, Ujiri became a beloved figure in the city.

Looking at a potential plummet down the standings, the Raptors instead surprised everyone by winning the Atlantic Division in 2013-14, the first of seven consecutive years the Raptors had a top-four seed in the Eastern Conference. That run is easily the high-water mark in Raptors history. In 2014, before the club’s first playoff game since 2008, Ujiri memorably said “F— Brooklyn” during a fan rally, endearing himself to the fans even more. He apologized, but his standing up for the city became a running theme of his tenure.

Most memorably, Ujiri pulled off a shocking trade for Leonard in July 2018. The trade came a few months after the Raptors won 59 games and finished first in the Eastern Conference for the first time. However, Toronto lost in the playoffs to LeBron James’ Cleveland Cavaliers for the third year in a row, going 2-12 against Cleveland in the postseason over three years. Months before that, Ujiri fired eventual Coach of the Year Dwane Casey, replacing him with Nick Nurse.

Both moves were debated, as the Leonard trade sent out DeMar DeRozan, a homegrown star who loved Toronto. DeRozan expressed that he felt a lack of reciprocal loyalty from the Raptors when the trade went down. That Leonard had only a year left on his contract and reportedly wanted to go home to play in Los Angeles after starting his career with the San Antonio Spurs made the deal even more risky.

However, Leonard and Nurse helped the Raptors win the title, with Leonard’s four-bounce series-winner over the Philadelphia 76ers going down as an all-time playoff moment. The Raptors beat the Golden State Warriors in six games in the finals, although Ujiri’s confrontation with a sheriff’s deputy, in which Ujiri was temporarily denied access to the court and shoves were exchanged at the arena, served as a pockmark on the evening. Both parties sued one another, with the suits dropped more than two years after the incident.

Recently, Ujiri said he wanted to get the Raptors another title in Toronto in part because that first championship had been so complicated.

“The day we won the championship, the only thing I was thinking about (was), ‘Are we going to re-sign Kawhi?’” Ujiri recalled at his end-of-season news conference in April. “There’s no time to enjoy it.

“I guarantee you I’m going to enjoy (the next title). And I guarantee you we are going to win here.”

He won’t get that chance.

The Raptors have missed the playoffs in four of the past five years. Ujiri’s inability to keep the Pascal Siakam-O.G. Anunoby-Fred VanVleet core happy and together frustrated him and the Raptors. Seeing Siakam go on to play such a vital role for the Indiana Pacers this year, when the Raptors got just three first-rounders plus Bruce Brown and Jordan Nwora in return for Siakam, made that trade look worse.

VanVleet left in free agency for Houston in 2023 and will start at point guard for a Rockets team with huge expectations next year. Ujiri dealt Anunoby in December 2023 for RJ Barrett and Immanuel Quickley. Ujiri signed Quickley and Scottie Barnes, the fourth pick of the 2021 draft and 2021-22 Rookie of the Year, to long-term contracts last summer.

Still, the Raptors finished 11th in the Eastern Conference and have gone 40-84 since the Siakam trade. The trade for Brandon Ingram signals the Raptors intend to battle for a playoff spot. If and when that happens, it will not be with Ujiri.

(Photo: John E. Sokolowski / Imagn Images)