Gary Trent Jr.'s four-year, $64 million return to Milwaukee was singled out as the most questionable move of 2026 free agency, with the Bucks paying starter-level money during a post-Giannis transition.
8.1 points, sub-40% shooting and just 1.0 rebound per game in 2025-26 underpinned the criticism, while Trent also ranked 149th of 159 qualifying players in defensive win shares.
Milwaukee's rationale appears tied more to continuity and locker-room value than production, but the price drew outsized scrutiny because his only clear plus last season was 36% shooting on 5.3 threes a game.
The broader review argued free agency has become more risk-averse, making Trent's contract stand out even more than other criticized deals such as Marcus Smart's two-year, $13 million pact in Houston.