With the news of Giannis Antetokounmpo leaving Milwaukee for Miami, it leaves the fate of a lot of players on this current Bucks roster up in the air. Myles Turner and AJ Green have already been some names explored for Toronto to consider as offseason targets, but there is actually a familiar face from Raptors' past who could be lined up perfectly for a second stint — only this time, his services might be a lot more important to their winning ways.
Enter, or in this case, re-enter Gary Trent Jr.
The 27-year-old swingman has a player option worth about $3.8 million to address this offseason, after signing a modest two-year, $7.5 million contract last summer. Given his down year in the 2025-26 campaign, where he struggled shooting the ball and couldn't quite establish a key role, Trent Jr. can simply opt into the final year to run it back with Milwaukee as the market could seem bleak as opposed to that current salary.
But now with the Bucks heading in a Giannis-less direction, no player should be considered safe on the roster now, and a guy like Gary Trent Jr. seems bound to feel the aftershock. Milwaukee's roster is going to fill up quickly, with new faces set to join them later tonight in the draft, and the new acquisitions from Miami taking up spots (at least right now).
Either way if Trent Jr. accepts his player option or opts out to become a free agent, the possibility of him rejoining the Raptors family presents some intrigue.
Should the Raptors explore a Gary Trent Jr. return this summer?
Toronto could use some shooters in their ranks, preferably those who won't cause a ton of financial strain on their already costly books, and the fact that Trent Jr. is an ex-Raptors fixture anyways — it makes the fit even more of a logical option to explore once again.
Sure, in the recent 2025-26 campaign, Trent Jr.'s shooting dipped from his 2024-25 highs, having shot just 38.7 percent from the field and 36.0 percent from three. But like another spark plug, microwave scorer I recently explored in Jordan Clarkson, GTJ is another one of those candidates who could give Toronto some much-needed veteran scoring depth.
Call it a flash in the pan or whatever, but let's not forget it was Trent Jr. who was essentially Milwaukee's second-best player (and an unsung hero) in their 2025 playoff sample. It didn't last long and kind of ended on a sour note too, but I still look to that as proof that Trent Jr. can rise to the occasion in key settings.
The Raptors are a hopeful young core that will look to be in the playoff mix again next year, despite the rising East competition, and having GTJ on your bench is a great add alongside pieces like Jamal Shead, Ja'Kobe Walter, Collin Murray-Boyles, and the impending No. 19 addition.
Rewinding back to his original Raptors days, fans can probably recall the streaky shooter label attached to Trent Jr., and perhaps his need for an extended role and being given the ball to be effective. I definitely remember some of those cold streaks, and those are certainly some red flags to note.
However, I think at this stage in his career where he's no longer a youngster and quickly reaching veteran status, GTJ's place to remain relevant in the NBA is by simply embracing his call as a role player.
And for a team like Toronto that can use all the role players to bolster their depth, figuring out a path to bring Gary Trent Jr. back for a redemption tour of sorts may just be an underrated Raptors offseason move waiting to be pulled off.
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