Why haven’t Raptors extended Gary Trent Jr. beyond 2023?

Before the Toronto Raptors signed Jakob Poeltl and Dennis Schroder in the early stages of free agency, they were given a major shot in the arm when prospective free agent Gary Trent Jr. decided to eschew the open market and pick up his player option for the 2023-24 season.

Trent opted into the final year of his contract by picking up his player option in a move that was fairly unexpected. Trent could have earned a huge multi-year deal in excess of $20 million per season on the open market, but he chose to play out the final year of his contract.

The Raptors were reportedly working towards an extension with Trent right after the signings of Poeltl and Schroder, but talk of such an extension has died down as trade rumors surrounding OG Anunoby and Pascal Siakam continue to swirl. Such hesitancy is strange, given what Trent means to this team.

A Trent extension won’t be so financially crippling that both Siakam and OG Anunoby will be forced out, and his style of play helps fill a need for an offensive-minded coach like Darko Rajakovic. What exactly is the hold-up here?

The Toronto Raptors must extend Gary Trent Jr.

Trent is the type of player that Toronto needs to target. Not only has he proven to be a well above-average shooter that can change the course of a game with his 3-point marksmanship, but he has made legitimate positive gains as an on-ball defender and turnover generator.

What makes Trent a truly worthwhile piece of the team’s future is the fact that his scoring could increase without Fred VanVleet. The fact that his spot-up shooting makes him effective without dominating the ball is a trait this team would be wise to prioritize.

While the futures of Pascal Siakam and OG Anunoby are still very much up in the air, gambling with Trent in free agency could come back to burn them. He helps with spacing (a huge need), won’t cost as much as either OG or Pascal (which would help mitigate the eventual Barnes extension), and has his best basketball in the windshield rather than the rear-view mirror.

The Raptors’ future might look murky, but it is very easy to see a world where they become a solid team based around Barnes as the main creator and the 1-2 punch of Trent and Gradey Dick on the perimeter. The hesitancy from Ujiri in this arena is unusual and slightly concerning.