Ex-Raptors swingman went from undesirable to undeniable in free agency

Gary Trent Jr. turned his offseason fortunes around... big time
Milwaukee Bucks v Golden State Warriors
Milwaukee Bucks v Golden State Warriors | Thearon W. Henderson/GettyImages

Gary Trent Jr. will be a hot commodity this summer.

You have to hand it to the former Raptors standout, who at one point seemed like a very integral complementary piece to Toronto's young core. However, for various reasons, the two sides were unable to reach a mutual agreement that would bring back the ex-Duke product on a long-term deal.

You might consider Trent Jr.'s middling contributions and inconsistent performances as a significant factor in his value declining somewhat. As a result, his name would rarely be mentioned alongside the team's other promising up-and-comers, hinting at a prelude to the eventual decision to let him walk in free agency.

I didn't have a doubt in my mind that some team in the NBA would be intrigued enough to offer a decent contract to see what Trent Jr. could bring to their squad. Even if his recent track record suggested otherwise, on his best night, GTJ could light it up the scoreboards in a flash.

Alas, my expectations were severely undermined, and I bet Trent was even more stunned when it came time to sign the contract he settled on at the conclusion of his 2024 free agency period: a one-year, veteran's minimum deal with the Milwaukee Bucks.

To put it simply, Trent's initial stint with Milwaukee looked quite bleak for a player who not long ago could post 30 or even 40-point games with the Raptors.

But you can't count out a gamer like Gary Trent Jr.

Trent Jr.'s solid 2024-25 campaign expected to see free agency reward

He worked diligently to improve his shooting and quickly became a key difference-maker in some crucial games for the Bucks. Notably, he delivered a standout performance in the NBA Cup Final, and despite fumbling the ball in the closing moments, he resembled the Trent Jr. of old in Game 5 of the Bucks vs. Pacers first-round series.

As Jake Fischer noted in his June 11 edition of The People's Insider for Marc Stein's Substack, extending the 26-year-old spark plug is a top offseason priority for the Milwaukee Bucks:

"The Bucks likewise have interest in retaining swingman Gary Trent Jr., sources say, although the veteran guard appears poised to generate a good amount of suitors."
Jake Fischer

Building on Fischer's point, it's clear that now, teams across the league understand exactly what they're getting by locking down Trent Jr. to a contract. Perhaps last offseason, it was too much of a risk for many teams, and to be fair, I didn't see much credible traction suggesting GTJ was going to become a hot commodity.

As we approach the 2025 free agency period, Trent Jr. will undoubtedly be one of the most attractive wing players on the market — a complete turnaround for a guy whose NBA prospects once looked very grim and dull.