What has been the most intriguing offseason in recent memory took an interesting turn after ESPN's Shams Charania reported that veteran guard Gary Trent Jr. is signing a four-year, $64 million deal with the Milwaukee Bucks . The deal, brokered by Klutch Sports' CEO, Rich Paul, and agent Lucas Newton, comes on the heels of Trent's worst season in the NBA since his rookie campaign.
The 6'5" guard averaged only 8.1 points per game on 38.7 percent shooting, including 36.7 percent from beyond the arc. He also tallied woeful 1.0 rebounds and 1.2 assists per game in 21.2 minutes of action.
Yet despite those subpar numbers, the son of Gary Trent is set to make more than more productive role players like Rui Hachimura and Anfernee Simons . The Bucks' decision to hand Trent this big of a deal raised a lot of eyebrows amongst the media men covering the NBA, including salary cap expert and longtime analyst Nate Duncan, who claimed the development is an "obvious circumvention" of the league's salary cap rules.
The league has seen its fair share of head-scratching deals like Timofey Mozgov 's four-year, $64 million contract in 2016 and Rashard Lewis ' six-year, $118 million deal in 2007. However, Duncan stressed that Trent's deal takes the cake.
"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," Duncan wrote on X.
"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?" he added.
Trent's new contract certainly smells fishy. Consider this: after a solid performance during the 2024-25 season, in which he averaged 11.1 points on 41.6 percent shooting from long range, Trent returned to the Bucks on a minimum contract worth only $3,697,105.
Now, despite his dismal showing last season, he is one of the Bucks' highest-paid players in an NBA landscape where teams are more wary of their salary cap use due to more stringent measures like the second apron. Making things even more puzzling is the fact that all four years of Trent's contract are guaranteed.
The working theory being floated is that the Bucks promised Trent a larger deal down the line if he agreed to play for the minimum, so they could build a more formidable team around two-time MVP Giannis Antetokounmpo . That obviously did not come to fruition as the Bucks finished with a 32-50 record and were well out of the playoff race by March.
The deal did not go unnoticed among the NBA's most veteran scribes and experts, with John Hollinger revealing he certainly didn't expect Trent to get such a large deal.
"Gary Trent Jr. played his way out of the rotation on a bad team last season; suffice to say, it seemed unlikely he would generate a bidding war for much above the minimum salary," he said . "Yet Trent becomes one of the few players this offseason to get four fully guaranteed seasons in a market where most role players have been squeezed on both years and dollars."
Mike Vorkunov, meanwhile, called the contract "curious" and "hard to explain."
"Trent has been a declining player for several seasons," he shared. "So, how does Trent go from a minimum bench player to getting the 10th-largest contract handed out in free agency this summer? All guaranteed, by the way."
This story was originally published by Basketball Network on Jul 13, 2026, where it first appeared in the Latest News section. Add Basketball Network as a Preferred Source by clicking here.
