​The Milwaukee Bucks are amid a full-scale rebuild. Since their 2021 NBA title, they’ve struggled to find the right mix around Giannis Antetokounmpo, and that ongoing challenge has fueled a flurry of trade rumors surrounding one of the most dominant players in league history. Despite their efforts to hold on as long as possible, the situation hasn’t evolved in their favor. This offseason, the Bucks ultimately traded Antetokounmpo to the Miami Heat, signaling a decisive rebuild from the ground up for the organization. In the process, however, they may have handed out one of the most questionable contracts in the NBA to Gary Trent Jr.
Trent began his pro career as a second-round pick and quickly proved to be the ideal role player for the Portland Trail Blazers. Portland aimed to construct a competitive lineup around Damian Lillard, potentially contending in the Western Conference, and Trent’s combination of perimeter defense and three-point shooting complemented that goal nicely. When the fit there didn’t materialize as hoped, Trent moved on to the Toronto Raptors, where he spent three seasons. The Bucks eventually acquired him in 2024, hoping his skill set would mesh well with Antetokounmpo—at least on paper. He initially signed for the minimum, intending to earn a larger contract extension through performance. That long-awaited payday arrived in the form of a four-year, $64 million deal, a commitment ESPN insider Shams Charania confirmed.
Sam Quinn of CBS chronicled the unusual sequence of events, noting, “Gary Trent was a pretty surprising minimum-salary free agent two years ago. Last year, he more or less played at the level of a minimum-salary player. Now he’s one of the most overpaid role players in the NBA.” Quinn went further to quantify just how steep the 64 million figure was. “Gary Trent got the eighth-highest total contract of 2026 free agency so far. Only Trae Young, Austin Reaves, Walker Kessler, Ayo Dosunmu, Tari Eason, Isaiah Hartenstein, and Coby White earned more. Pretty much every metric paints Trent as a negative last season.”
The analytics frame Trent as far from a productive impact player. Yet even the raw numbers are striking. He averaged 8.1 points, 1.2 assists, and 1 rebound per game, shooting a woeful 38.7 percent from the field and just 36 percent from three-point range. With his defense regressing as well, the decision to sign him becomes increasingly puzzling by the day. This has prompted strong reactions from observers, including The Athletic’s Sam Vecenie, who urged the NBA to reexamine what he called a “truly nonsensical contract,” given that Trent posted 8 PPG and shot 39 percent from the field over 22 minutes per game last season.
Amid an offseason that featured a free-agent pursuit by LeBron James, and high-profile moves involving Antetokounmpo, Ja Morant, and Jaylen Brown, this contract-related development stands out in a crowded field of notable headlines. Andy Bailey of Bleacher Report captured that sentiment, underscoring how this particular deal has loomed large in discussions about the league’s most perplexing strategic moves.