Looking Back at Masai Ujiri’s Toronto Raptors’ Tenure

Photo: Former Toronto Raptors’ Vice President Masai Ujiri during a press conference. Photo credit: Mark Blinch, 2023 Getty Images

On May 31, 2013, Masai Ujiri left the Denver Nuggets’ organization for the Toronto Raptors, where he was named Executive Vice-President of Basketball Operations. 

On Friday June 27, 2025, Ujiri’s tenure as Vice-President and Chairman of the Raptors ended as he and Maple Leaf Sports and Entertainment decided to part ways. 

The move marks the end of a successful era in Toronto that followed Brian Colangelo’s time as President and General Manager. Colangelo had been with the Raptors since 2006 and drafted DeMar DeRozan and Jonas Valanciunas and traded for Kyle Lowry in his time there, all moves that led the Raptors to playoff contention - the second round and Eastern Conference Finals’ specifically - from 2015-2018. 

Under Ujiri, the Raptors had eight winning seasons: 

2013-14: 48-34

2014-15: 49-33

2015-16: 56-26

2016-17: 51-31

2017-18: 59-23

2018-19: 58-24

2019-20: 53-19

2021-22: 48-34

Overall record under Ujiri: 545-419

Win percentage: 56.5% (fifth-best in the NBA since 2014, per StatMuse).

Dwane Casey, who served as the Raptors’ head coach from 2011-2018, won the 2018 NBA Coach of the Year. 

Nearly four months to the day of Ujiri’s hiring, the Raptors on January 30, 2013 traded for Memphis Grizzlies’ wing Rudy Gay. The tandem of he and DeRozan lasted just eleven months - the Raptors won thirty-four games in 2012-13 and were 6-12 through the first eighteen games of 2013-14 - before they on December 8, 2013 dealt Gay to the Sacramento Kings.

The tandem of Ujiri and still-GM Bobby Webster drafted very well in the late 2010s. In 2016, the Raptors with the 27th overall selection drafted a lowkey forward out of New Mexico by the name of Pascal Siakam. At the conclusion of that draft, the team signed Wichita State guard Fred VanVleet. In 2017’s draft, the team selected OG Anunoby 23rd overall. All became core players on the 2019 championship team. The Raptors also drafted center Jakob Poeltl ninth overall in 2016, but traded him along with DeRozan to the San Antonio Spurs in July of 2019 for Kawhi Leonard and Danny Green. The Raptors re-acquired Poeltl in a February 2023 trade, and the center has been a solid performer for the club.

Siakam is a 3-time all-star and in 2019 won the league’s Most Improved Player award. On January 19, 2024, the Raptors traded Siakam to the Indiana Pacers. This spring, the 31-year-old was a major catalyst in the Pacers’ run to a championship as one of their top two players. Anunoby led the NBA in steals in 2018-19 and has emerged as one of the league’s best defenders as he was named in 2023 to the All-Defensive 2nd team. He is currently one of the New York Knicks’ best players who can score and defend. VanVleet was an all-star in 2022 and now is the engine behind the Houston Rockets, who were the No. 2 seed in the Western Conference in 2024-25. On June 26, the 31-year-old re-upped in Houston for two years at $50 million.

Anunoby was traded to the Knicks in December of 2023 in a trade that yielded the Raptors forward RJ Barrett (from Mississauga, ON) and guard Immanuel Quickley. A few months ago in February, the Raptors traded for New Orleans Pelicans’ forward Brandon Ingram, giving them a supreme isolation scorer.  

The Raptors drafted Scottie Barnes out of Florida State with the fourth overall selection in 2021. Barnes has emerged as the Raptors’ cornerstone, a versatile forward who can score, distribute, rebound, and defend. The 6 foot, 7 inch forward was the 2021 NBA Rookie of the Year and was a 2024 All-Star. 

Of course, the biggest deal that Ujiri and Marks made (and the biggest in franchise history) was the acquisition of Leonard with Green in July of 2019 for DeRozan and Poeltl. The deal, along with the acquisition of Serge Ibaka in 2017 and a deadline deal in 2019 for Marc Gasol, completed the 2018-19 Raptors’ core and allowed them to win the 2019 NBA Finals. The special season capped off the most exciting and unforgettable time in franchise history. 

In the years after Leonard’s summer 2019 departure, the Raptors have rebuilt, with VanVleet, Siakam, and Anunoby now gone. Barnes is their building block and now with Ingram, Quickley, Barrett, and 2023 draft choice Gradey Dick, the Raptors have quality cornerstones for the future. 

When Ujiri arrived in 2013, he was taking over a team that, from 2006 to 2013, Colangelo had done his best to turn into a winner. Colangelo, who had previously been with the Phoenix Suns, traded disappointing 2004 draft pick Rafael Araujo to the Utah Jazz, and despite drafting forward Charlie Villanueva in 2005 and trading for Jermaine O’Neal in 2008 - both in efforts to try and pair all-star forward Chris Bosh with another big man to form a variation of Twin Towers in Toronto - the moves did not pan out. Colangelo ended up trading Villanueva in June 2006 to the Milwaukee Bucks for point guard TJ Ford who was a solid leader for the team. A decision that Colangelo can be criticized for is the selection of Andrea Bargnani with the No. 1 overall pick in 2006 when LaMarcus Aldridge, a 7-time all-star and probable Hall of Fame big man, was taken second overall. In June of 2006, the Raptors hired EuroLeague executive Maurizio Gherardini and went on a run where they sought talent from overseas. One of those talents was a Spanish forward by the name of Jorge Garbajosa, who showed talent as a 29-year-old rookie but suffered a horrific leg injury during the 2007-08 season. The Raptors missed the playoffs every season from 2008 to 2013. After seven years with Colangelo, it was time to move on.

After twelve years with Ujiri, it was also time to move on. Under the soon-to-be 55 year old’s tenure, the Raptors accomplished their goal in improving, ultimately culminating in the pinnacle of success as NBA champions. However it is clear that both the organization and Ujiri sensed that it was time for a change.