Gary Trent Jr. signed four-year, $64M deal with Milwaukee Bucks, raising eyebrows among NBA insiders
Gary Trent Jr. signed four-year, $64M deal with Milwaukee Bucks, raising eyebrows among NBA insiders
Published Jul 13, 2026 • 3 minute read
Gary Trent Jr. of the Milwaukee Bucks dribbles the ball against Dylan Harper of the San Antonio Spurs during a game earlier this year. Getty ImagesSee more Toronto Sun on Google — save as a Preferred Source
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As Kawhi Leonard’s return to Toronto remains up in the air with the NBA’s investigation into the Clippers and its relationship with the bankrupt fintech company Aspiration, another former Raptor’s new contract has some alarm bells ringing.
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Over the weekend, the Milwaukee Bucks signed ex-Raptors guard Gary Trent Jr. to a four-year deal worth $64 million US.
“Free-agent guard Gary Trent Jr. has agreed to a four-year, $64-million deal to stay with the Milwaukee Bucks,” ESPN’s Shams Charania reported on Saturday. “The Bucks and Trent’s reps worked through negotiations since the NBA Finals ended in mid-June while also sorting through sign-and-trade possibilities from interested teams over the last week. The sides moved toward completing a new deal together Saturday.”
Free agent guard Gary Trent Jr. has agreed to a four-year, $64 million deal to stay with the Milwaukee Bucks, Klutch Sports CEO Rich Paul and agent Lucas Newton tells ESPN. pic.twitter.com/hZMDvuA816
— Shams Charania (@ShamsCharania) July 11, 2026
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The deal almost instantly raised eyebrows among NBA fans and insiders with some claiming that this was a clear incident of salary cap circumvention.
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While Trent is a fine role player, the fact of the matter is that he was coming off two straight seasons in which he played for the veteran minimum in Milwaukee and only saw his numbers decline. Now he is one of the highest-paid players on the team.
Of note, after Trent completed his second season with the Bucks, Milwaukee secured his Bird rights, which allowed the team to re-sign him over the salary cap.
But as NBA insider Nate Duncan pointed out, the new contract appears to be “obvious circumvention,” inferring that there could’ve allegedly been a handshake deal between the Bucks and Trent before he signed the minimum contracts to pay him more later on.
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“Gary Trent getting 4/$64 (million) after the year he just had is obvious circumvention and should be punished by the league,” wrote Duncan on X. “This would fall under the provision that there is no possible explanation other than circumvention.
“If judging it purely on its merits, is 4/$64M for Gary Trent Jr. the most absurd deal in NBA history relative to the market if judging at the moment the deal was signed?”
Gary Trent getting 4/$64 after the year he just had is obvious circumvention and should be punished by the league. This would fall under the provision that there is no possible explanation other than circumvention.
— Nate Duncan (@NateDuncanNBA) July 11, 2026
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Duncan also noted that while cap circumvention can be hard for the NBA to prove, “there’s the provision to allow punishment when a contract cannot rationally be explained other than by circumvention.”
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Many users on social media had similar thoughts while also questioning Milwaukee’s motives.
“What are the Bucks doing?” one user commented on Reddit. “Either circumventing or your (front office) is absolutely (terrible).”
“Genuinely what other explanation is there? You could literally sign a two-way player for similar or even better production,” another replied.
Many others joked that having the Bucks simply be forced to pay Trent — who averaged just 8.1 points per game last season, his worst mark since his rookie season — would be punishment enough.
Trent’s new deal and the controversy that arose from it came at a time when the investigation into alleged cap circumvention by the L.A. Clippers involving Leonard and former team sponsor Aspiration is back in the spotlight.
Last week, the Raptors and Clippers announced that the pending trade to send Leonard back to Toronto was on hold until the NBA completes its investigation into the matter.
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