The league’s collective bargaining agreement contains a clause against prior agreement, which the league believes the Bucks may have broken by promising a larger future contract in exchange for Trent taking a pay cut a couple of years ago.
The six-foot-four guard joined Milwaukee in 2024 by signing a two-year, $7.5 million contract.
At the time, he was coming off three seasons averaging 18, 17, and 14 points, respectively, for the Toronto Raptors, while shooting around 38 percent from three-point range.
After signing for just the veteran minimum, Trent’s output dropped, averaging 11 points in 2025 on 42 percent shooting from three-point range, but he excelled in a five-game playoff run, averaging 19 points and nearly three steals on 50 percent three-point shooting.
However, in 2026, Trent’s regular-season averages dropped further, averaging just 8 points on 36 percent three-point shooting. Milwaukee did not make the playoffs.
Despite these most recent averages being the lowest since his rookie season in 2019, Trent opted out of his player option to become a free agent, and Milwaukee re-signed him in a four-year, $64 million contract on July 11.
This represents an average of 300 percent more per year than the two parties’ last contract, and Trent is set to earn $15.2 million in the 2026–27 season.
Milwaukee’s circumstances were vastly different when it signed Trent to the first contract. The team won a championship in 2021 and remained focused on competing for another with superstar Giannis Antetokounmpo, who was injured during the Bucks’ first-round loss to the Indiana Pacers in 2024.
This off-season, the team traded Antetokounmpo to the Miami Heat and received a package of younger players, including 26-year-old Tyler Herro and 25-year-old Jaime Jaquez Jr.
Milwaukee no longer has the same aspirations of championship contention and appears to be committing to a rebuild.
The investigation was launched last September after a report alleged that the team paid Leonard through a $28 million endorsement contract between Leonard and Aspiration Fund Adviser, a now-bankrupt California-based sustainability services company.
The Clippers announced a $300 million partnership with the company about a month after it signed Leonard to a four-year, $176 million extension in 2021.
The NBA has put the Clippers-Raptors trade involving Leonard, agreed upon a couple of weeks ago, on pause until the investigation is complete.
The team has denied any wrongdoing on multiple occasions, saying it ended its relationship with the company after two years because the contract was in default.
Last year, Aspiration co-founder Joe Sanberg pleaded guilty to two counts of wire fraud and last month was sentenced to 14 years in prison for falsifying financial records.
