I was very sad when I heard Gary Trent Jr. was leaving the Toronto Raptors to join the Milwaukee Bucks last offseason, because while he could make you scratch your head with some very questionable performances and stretches, GTJ easily grew into one of my favorite players on the entire roster during his time here.
That first season when he came over from the Blazers had me 100% sold on the Gary Trent Jr. stocks, and I was passionate enough to tell everybody about it. But I slowly realized, and I think the Raptors organization did too, that Trent Jr. wasn't quite going to be the continuous developmental piece that was initially hoped. Trent might have hit his ceiling as a spark plug, but largely streaky shooter, and that was evident in the seasons that followed his 2021 breakout. So they let him walk as I mentioned and he ended up with the Bucks.
There, I was absolutely stunned to see how horribly GTJ was performing in the early part of last season, where he was honestly looking unplayable and perhaps drawing dangerously close to getting cut out of the Bucks' rotation. But GTJ stood the course and eventually he'd regain his shooting edge, getting his three-point shot back to where it looks best, as it sat at 41.6% this past season. And while that was just one part to Trent Jr.'s return to form, he truly put this on full display with a massive 2025 playoff showing.
Trent Jr. averaged 18.8 points on 51.6% field goal shooting and 50% from three in the Bucks' playoff series with Indiana. It was a crucial time for GTJ to step up, especially since Milwaukee lost its secondary star, Damian Lillard, in the midst of it all. I noted this right after it happened and still believe it to this day. Although the Bucks ultimately lost and Trent Jr. made a costly slip-up, it served as the perfect ad campaign for an impending free agent.
Gary Trent Jr. opted to stay with Milwaukee on team-friendly deal — but why?
But alas, this offseason, Trent Jr. took the gentlemen's route and chose to re-sign with the Milwaukee Bucks on a two-year, $7.5 million contract, with the second year being a player option. It honestly stunned me that even after proving his worth in the recent season, he decided to run it back with the team that initially took a chance on him.
Yes, I definitely believed GTJ was worth much more than just a measly $3.75 million per year, but since he has a player option he can easily opt out of, this might simply be Trent Jr. betting on himself again this season and seeing what his market looks like next year, similar to what I suggested for another ex-Raptor, Chris Boucher.
So I don't necessarily know if 'lowball' is the right term to use here, because Trent Jr. could have certainly warranted more money based solely on his playoff breakthrough. But he chose to return on a team-friendly deal with a Bucks team that might be in its last stages, almost making a desperate attempt at chasing another championship with Giannis Antetokounmpo leading the way. Business-wise, it doesn't look so smart, but character-wise, it shows that Trent Jr. is considering the bigger picture ... so hats off to him.