It feels like that Gary Trent Jr. will leave the Milwaukee Bucks this summer after things did not go quite according to plan last season. As the guard seeks an opportunity where he can play actual minutes, it wouldn't be surprising if he made his way back to Portland. Trail Blazers General Manager Joe Cronin made it clear that the team needs more shooting this summer, and Trent would give them just that.
"The Spurs series showed us that we don't shoot the ball well enough. Shooting is something we knew we were deficient in. [Damian Lillard] will definitely help us, but something we need to address going forward. We played a lot of possessions in the mud."
A return to Portland would make sense for Trent
Outside shooting has always been Trent's best attribute. For his career, he's shooting 38.7 percent from downtown on 6.1 attempts per game. A player like that could do Portland a lot of good after they shot just 30.8 percent from deep in their first-round series with the San Antonio Spurs, which is tied for the second-worst percentage among all NBA Playoff teams.
Making Portland all the more likely is that Trent already has ties to the organization. The wing began his career there in 2018-19, spending his first two and a half years there. Returning to Portland would also reunite Trent with Damian Lillard, the star guard he spent time with already with the Trail Blazers and Milwaukee Bucks before Dame was shockingly waived and stretched to sign Myles Turner.
It wouldn't be surprising if Lillard was already doing some behind-the-scenes recruiting of Trent to pitch them joining forces for a third time.
Trent still has the tools to be a useful rotational player
Trent's time in Milwaukee didn't go as planned. Initially pegged as an outright steal, his role kept changing, preventing him from getting into a groove. When he was finally given a legitimate role, the wing dazzled in the postseason, averaging 18.8 points and 2.6 steals last year. Poised to be a major contributor this past season, Doc Rivers never gave him that same opportunity consistently.
After betting on himself by taking another team-friendly deal last summer, Trent averaged just 21.2 minutes per game in 2025-26, the fewest since his rookie season. That's not going to help him be a steady contributor to this team. It could guarantee that he declines his player option to test the free-agent market and see where he can find an actual opportunity, though.
It will be frustrating if Trent goes elsewhere and performs at a high level, but it would be on-brand after the last few ugly seasons of Milwaukee Bucks basketball.
Stay tuned for more Milwaukee Bucks analysis.
Add us as a preferred source on Google