Raptors' front office might have their jobs on the line this season

Four years ago, the Toronto Raptors’ front office was flying high.
Winning the 2019 NBA title — the first in the franchise, and of course, Canadian basketball history — team president Masai Ujiri and general manager Bobby Webster forever etched themselves into the country’s sporting landscape.
After undergoing a high-risk trade for Kawhi Leonard that ultimately culminated in the superstar staying just one season — but winning an NBA Finals MVP along the way — Webster and Ujiri could seemingly do no wrong in the hearts of Raptors fans.
But it’s hard to see the same type of praise and trust heaved on Toronto’s front office these days.
And while there was a time when calling for a shakeup in the front office might’ve seemed blasphemous, there’s a reason there are plenty of “fire Masai” posts flooding social media in recent days.
Coming off a 41-41 season where the team floundered out of the play-in round, things haven’t gone much better for the team this summer.
Most notably, the team hasn’t made any sort of major move, while losing veteran point guard Fred VanVleet for free in free agency to the Houston Rockets.
Trading for Damian Lillard wasn’t the direction Toronto either wanted to — or was able to — take, as they reportedly weren’t willing to part ways with any of Scottie Barnes, O.G. Anunoby, or Pascal Siakam.
But fans are antsy for something, anything to make the team better, and for the front office to provide some sort of clear direction for where the team is heading.
It’s not just fans who are having their doubts about Toronto’s leading group — the team was recently voted worst offseason by other executives around the league in a 15-person poll conducted by ESPN’s Tim Bontemps.
The team’s won just one playoff series since their title, a 4-0 sweep over a heavily depleted Brooklyn Nets side in the NBA bubble back in 2020.
In the four years since winning a title, the Raptors have made precisely six trades, with four of the players acquired by those trades remaining on the roster: Jakob Poeltl, Precious Achiuwa, Gary Trent Jr., and Thaddeus Young.
Poeltl is the only one of the four slated to be a regular starter for the Raptors this coming season, with Achiuwa and Trent expected to find themselves among the team’s bench rotation.
Young, at age 35, didn’t play more than 10 minutes in a game past February 28 last year, and didn’t play any of the team’s final 13 regular season games.
Perhaps he finds a late-career resurgence with new head coach Darko Rajaković, but he seems nearly at the end of his 16-year NBA career.
In the end, it’s really not all that impressive a group to join the fold, while 12 of the 15 players from Toronto’s championship roster — ie, everyone but Pascal Siakam, Chris Boucher, and O.G. Anunoby — have now left the organization in one way or another.
The issue, though, isn’t that the players have come and gone, as the NBA is a transaction-heavy league. The Phoenix Suns, who made the NBA Finals in 2021, see just Devin Booker as the only player remaining from that roster after shipping out DeAndre Ayton as part of yesterday’s three-team deal.
Rather, the issue is that for all the pieces that have gone out, the Raptors seem set for another year in mediocrity unless some sort of massive roster shift is underway.
Free agency hasn’t exactly been kind to the front office either in the last few years: not a single veteran free agent signed with the team since 2019-20 has made it to the 100 games played mark.
Webster and Ujiri have likely earned at least one more kick at the can before firing them will have seriously been considered by the MLSE board.
But if another season comes and goes without any clear direction of the team’s future, the rumblings about their job security might just turn up to full volume.