The Milwaukee Bucks have approached this offseason differently compared to years past after trading former MVP and franchise cornerstone Giannis Antetokounmpo to the Miami Heat. 

The Bucks acquired multiple players and draft picks from the Giannis trade, but they haven't been big spenders in the free agency period. Just recently, however, they went against that pattern of being passive this summer and re-signed guard Gary Trent Jr. to a 4-year $64 million deal. 

Trent has been with the Bucks since 2024, and in his time with the franchise, he has averaged 9.7 points, 1.7 rebounds, and 1.2 assists. He was brought into Milwaukee to be another shooting threat as well as a player who can defend the perimeter effectively. 

His first season in Milwaukee saw his most production as he averaged over 11 points per game. In 2025-2026, he saw a dip in production, and that could have been a result of the sudden change in the rotation thanks to the absence of Giannis Antetokounmpo. 

Gary Trent Jr.'s $16 million per year contract has raised some questions from Bucks fans, considering he is coming off a down year this past season. Trent averaged just 8.1 points per game on 38.7 percent shooting from the field. 

Trent's shooting percentage from the field is nearly a 5 percent dip from 2024-2025, and if he can't find a way to improve in 2026, this contracts may not serve the Bucks well moving forward. 

Gary Trent had big games for the Bucks in his first season there. In the postseason, he had multiple 30-point games against the Indiana Pacers, and he showed he could be a serious threat from the perimeter. In that series against the Pacers, he also averaged 2.6 steals per game, showing he can be a solid player on both ends. 

While the Bucks saw his value coming from his first season with the franchise, this contract is risky, and it's tough to imagine that one season two years ago warrants a contract like this. 

Milwaukee has a lot of younger players who will need to play significant minutes to see growth. Brayden Burries and Nate Ament have holes in their game that will only be fixed the more they play. Ryan Rollins is coming off a big season after seeing significant playing time for the first time in his career as well. 

A contract like this could mean the Bucks are ready to commit to having Gary Trent Jr. on the court as a starter, and the coaching staff will have to navigate through getting him minutes while giving younger players minutes to develop. It will be on Trent to have a bounce-back season.