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Bucks potentially screwed themselves with timing of ugly Gary Trent Jr. deal

Had it happened earlier, perhaps no one would have batted an eye.
ByDalton Sell
Milwaukee Bucks guard Gary Trent Jr (5) reacts against the Philadelphia 76ers in the third quarter at Wells Fargo Center on April 3, 2025.
Milwaukee Bucks guard Gary Trent Jr (5) reacts against the Philadelphia 76ers in the third quarter at Wells Fargo Center on April 3, 2025. | IMAGN IMAGES via Reuters Connect

The Milwaukee Bucks handing Gary Trent Jr. $64 million after the year he just had would have been a strange move no matter when it happened, but the actual timing was certainly puzzling. As reported in a new article from The Athletic's Joe Vardon (subscription required), handing Trent this deal almost two weeks into free agency highlighted it being an overpay, fueling the investigation even further.

Bucks should have re-signed Trent sooner

The best time to overpay, especially if there is any wrongdoing taking place, is as soon as possible. As Vardon notes, had the Milwaukee Bucks re-signed Trent in the first few hours or days of free agency, the general reaction would have been mockery, given the guard's down year. However, doing so after almost two weeks of being allowed to raised eyebrows, hinting that something might be going on.

The first wave of NBA Free Agency is when teams are their hungriest—and likely aren't thinking their hardest. Teams are willing to spend big to lock down desirable players because they don't want other suitors snagging them. It often leads to overpays, but that's the price of business. If the Bucks had made this deal earlier, the reaction might not have been as condemning.

Instead, the Milwaukee Bucks and Trent didn't agree to the deal until July 11. By then, most teams were out of money and couldn't afford to pay Trent the $64 million he got. The Bucks were bidding against themselves, and the league clearly thinks it looks fishy enough to open an investigation into a potential cap circumvention case.

Bucks awaiting NBA's verdict in Trent case

As Vardon notes, the Milwaukee Bucks have complied with the investigation thus far. They maintain that they gave Trent a deal they felt was his market value. Further backing up that claim is that ESPN insider Shams Charania reported on the Shump Street with Iman Shumpert podcast that the Bucks discussed a sign-and-trade involving Trent at a similar financial figure with at least one suitor.

Nothing obviously materialized, but it adds validity to Milwaukee's case that at least someone was considering giving him something similar financially.

There is no telling how long this takes. The Kawhi Leonard cap circumvention scandal, which went far deeper than this, took over a year to resolve. The Milwaukee Bucks certainly wouldn't want this black cloud hanging over the franchise for that long, but the ball is in the NBA's court right now.

Stay tuned for more Milwaukee Bucks analysis.

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