The Milwaukee Bucks have already made plenty of noise this offseason, but Gary Trent Jr.’s new deal is the one that really sent people around the league talking.
Before the draft, NBA insider Marc Stein reported that conversations around the league pointed to Milwaukee possibly working on a three-year contract worth about $45 million to keep the veteran guard. Even that number would have marked a major jump for Trent, who had spent his previous two seasons with the Bucks on deals that paid less than $4 million per year.
Instead, Trent and Klutch Sports landed a fully guaranteed four-year, $64 million contract.
That price tag raised eyebrows in front offices across the league. Rival executives reportedly questioned both the size of the deal and its length, especially after Trent averaged just 8.2 points per game while shooting a career-low 38.7 percent from the field in 2025-26. There’s also been speculation about how the league office might view such a steep raise after back-to-back bargain contracts.
Still, Milwaukee is clearly betting on the version of Trent that made him such a sought-after role player in the first place. He was once valued for his two-way shooting, and the Bucks are banking on that version showing up again.
Trent’s path to this point started when the Sacramento Kings picked him 37th overall in the 2018 NBA Draft and then traded him to the Portland Trail Blazers. He built himself into a dependable perimeter scorer in Portland before taking another step forward with the Toronto Raptors, where he posted a career-high 18.3 points per game in 2021-22.
After two seasons in Milwaukee, though, his numbers fell off sharply. Even so, the Bucks still made the long-term commitment, and the contract now stands out as one of the most surprising moves of the 2026 offseason.
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