The NBA’s crackdown on cap circumvention has already landed hard in Los Angeles, and Boston could end up feeling the ripple effects of the league’s next move too.
The Clippers got hit with the full weight of the league after an investigation tied to Kawhi Leonard. The punishment was severe: five first-round picks gone, a $30 million fine, Steve Ballmer suspended for a year, Gillian Zucker suspended without pay for a year, Lawrence Frank suspended without pay for six months and on leave, and Leonard fined $700,000 without a suspension.
Now the Milwaukee Bucks are under their own active salary cap circumvention investigation, and the deal that put Gary Trent Jr. in the spotlight is the reason why.
Milwaukee signed Trent in July to a four-year, $64 million contract, a striking number for a player who averaged 8.1 points, 1.2 assists and shot below 40 percent from the field in the 2025-26 campaign. It was an especially eye-catching payday given that his previous contract paid him an average annual value of just $3.8 million over the last two seasons.
That kind of jump is what set off the alarms. The NBA investigation may uncover something else, but on the surface it has the look of a deal that pushed right up against the line. As Yossi Gozlan and Sam Quinn discussed on the Third Apron Podcast, it feels naive to think Leonard’s case is the only example of this happening in the NBA.
Proving a cap-circumvention case is no easy thing, especially when teams are working through Bird rights and the gray areas that come with them. But when a franchise is as open about it as the Bucks may have been with Trent, the league has more to work with.
And if Milwaukee does get punished, Boston has reason to care.
The Bucks are in the middle of a rebuild after accepting that a return to title contention with Giannis Antetokounmpo at the helm was unlikely. He is now with the Miami Heat, and Milwaukee has moved into a new phase built around young talent.
That puts pressure on the players who are supposed to carry the next version of the team, including this year’s lottery picks, Brayden Burries and Nate Ament. Potential is nice, but it still has to turn into production, and there’s no guarantee that happens.
If the Bucks lose draft picks, even if it’s not at the level of the Clippers’ punishment, it would make that job harder. The league’s Eastern Conference race is already a grind, and Milwaukee’s ability to rise will matter as other teams see their windows start to close. If the Bucks’ climb gets steeper, that works in Boston’s favor - and in the favor of the rest of the teams on that side of the bracket.
In Other News...
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Former All-Star DeMarcus Cousins only added fuel to the reaction by voicing disappointment in Tatum for not stepping in during the process. With Brown now in a different uniform, the breakup has done more than alter Bostons roster structure - it has also set up a new layer of rivalry, with Tatum and Brown suddenly on opposite sides of the league and Celtics fans left sorting through what this means for what comes next. [Read more 🡒]
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What makes the situation even more interesting is how little is known about the back end of those talks. It is not clear whether Charlotte had real interest in Carter or whether he preferred the waiver route, but the end result was the same: he became available and eventually landed with the Celtics on a non-guaranteed deal. For Boston, that creates a low-risk chance to evaluate a young player whose route here was shaped as much by what did not happen as by what did. [Read more 🡒]
Celtics Face A Risky Payton Pritchard Decision They Can't Fully Control
Payton Pritchard will be eligible to sign a three-year extension with the Celtics starting Oct. 1, giving Boston a chance to lock in one of its most important rotation guards before the situation gets more complicated. Because of the NBA salary cap rules tied to his current contract and the estimated average player salary, the Celtics can offer a deal with a first-year salary around $21.3 million, a number that could reach about $69 million over three seasons.
Pritchard, though, controls the bigger part of the decision. He can take the security of that extension or keep moving toward unrestricted free agency in 2028, where a stronger market could mean a richer payoff. For Boston, that creates a familiar kind of roster tension: the team can put a real offer on the table, but it cannot force timing, and it cannot fully control what Pritchard decides to do with it. [Read more 🡒]