Earlier this offseason, the Milwaukee Bucks re-signed guard Gary Trent Jr. to a 4-year, $64 million deal. Trent has been with the Bucks since the middle of the 2024 season, and after a down year in 2025-2026, he gets a near $12 million raise. 

Since the contract signing was announced, a league spokesperson told ESPN's Shams Charania that it has been put under investigation by the NBA. Trent's raise and his performance last season may have been a red flag to the league and could have prompted an investigation. 

ESPN's Brian Windhorst explained the situation and where this investigation is coming from, and he believes the investigation is also happening because this kind of deal is being made by the same team that underpaid Gary Trent during the 2024-2025 season. 

"What has raised the flag is that [Gary Trent Jr.] would be perceived by the league as being overpaid by the same team that he was underpaid for by the last two years," Windhorst said. 

While Gary Trent Jr. has proven he can be a solid 3 & D guard for a contending team in the past, his current production has not warranted a 4-year contract. Brian Windhorst mentioned players like Donovan Mitchell and Victor Wembanyama are the type of players to get a 4-year contract this offseason, and Trent doesn't fit the criteria. 

Last season, Gary Trent Jr. shot 36 percent from three-point range and only scored 8.1 points per game. He was one of the veteran players on the Bucks that many expected to depart from the team following the Giannis Antetokounmpo trade that sent him to the Miami Heat. 

He has been a durable player in the last few seasons in the NBA, playing 65 games last season and 74 in 2024-2025. Even though he has played a lot, he has not done enough to earn a long-term deal. 

Another issue with this contract is the Bucks' overall guard depth. Milwaukee added Tyler Herro in the Giannis trade and drafted guard Brayden Burries with the 10th overall pick in the 2026 NBA Draft. They also have young guard Ryan Rollins returning, and he's coming off a career year. 

The Bucks' coaching staff will need to figure out how to incorporate all four players in a proper manner while being able to develop Brayden Burries. Many expected the Bucks to go younger after trading their franchise cornerstone, but now they face challenges in finding the right backcourt rotation going into next season.