July 15, 2026

Gary Trent Jr.’s Contract with Milwaukee Bucks Raises Concerns

The Milwaukee Bucks recently signed Gary Trent Jr. to a four-year contract extension worth $64 million, keeping him with the team until the end of the 2029-2030 season. Last season, Trent participated in 65 games, starting in 21 of them. His performance saw a career-low average of 8.1 points, 1.2 assists, 1.0 rebounds, and 0.5 steals per game over 21.2 minutes. He also had his worst shooting season, hitting only 38.7% from the field. These stats have declined yearly for the past four seasons. Trent will be 31 years old by the contract’s conclusion, and his performance has puzzled many NBA observers.

Trent’s Average Annual Value (AAV) of $16 million places him alongside players such as Dennis Schroder, Quentin Grimes, Nickeil Alexander-Walker, Max Strus, Lu Dort, and Klay Thompson, all of whom delivered better statistics last year. ESPN’s Tim MacMahon criticized Trent’s contract on “The Hoop Collective,” noting his negative win shares, box plus-minus, and VORP (Value Over Replacement Player), likening the deal to a nearly full mid-level exception.

“The contract stinks,” said MacMahon, urging NBA commissioner Adam Silver to investigate further.

Some have even suggested a formal inquiry, considering the possibility of an undisclosed agreement between Trent and the Bucks. MacMahon recommended, If I was Adam Silver and I’m some of those head honchos in the league office, I’d sniff around. I’d sniff around a little bit on this one.

Brian Windhorst added that current investigations involving Kawhi Leonard might prompt the NBA to scrutinize Trent’s contract. Leonard, the Los Angeles Clippers, and Aspiration face cap-circumvention allegations. Reports allege that Leonard was slated for a $28 million endorsement by Aspiration, a now-defunct company backed by Clippers owner Steve Ballmer. The arrangement purportedly required minimal effort from Leonard.

The trade involving Leonard and the Toronto Raptors remains pending due to ongoing investigations. Further complications arose with reports of another unreported endorsement involving Leonard.

The NBA’s focus on potential financial misconduct has spotlighted the Gary Trent deal. As the league addresses salary cap violations with one team, increased scrutiny on other suspicious deals, including Trent’s, appears inevitable.

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