The Milwaukee Bucks are already enduring one of the most difficult periods in recent franchise history. But according to ESPN insider Brian Windhorst, their problems could soon become considerably worse.
With the NBA investigating possible salary-cap circumvention surrounding Gary Trent Jr.’s controversial four-year, $64 million contract, Milwaukee could be facing severe penalties, including the loss of valuable draft picks and lengthy suspensions for team executives.
And Windhorst believes the outcome is becoming increasingly predictable. Speaking on ESPN’s The Hoop Collective podcast alongside Tim MacMahon and Bobby Marks, Windhorst revealed that people around the league expect the Bucks to be found in violation of NBA rules.
“Everybody in the league expects a guilty finding in Gary Trent,” Windhorst said. “If that doesn’t happen, it will be an upset.”
The investigation centers on the circumstances surrounding Trent’s surprising contract extension in July. The 27-year-old initially joined Milwaukee on a minimum contract in 2024 before signing a two-year, $7.5 million agreement the following offseason. After earning approximately $3.7 million during the 2025-26 campaign, he declined his player option and subsequently received a four-year deal worth $64 million.
The financial commitment immediately raised eyebrows. Trent had just completed one of the least productive seasons of his career, averaging 8.1 points while shooting 38.7 percent from the field.
Yet Milwaukee suddenly rewarded him with a contract worth an average of $16 million annually. The NBA is examining whether the organization had previously promised Trent a substantial future payday in exchange for accepting smaller contracts, allowing the Bucks to retain his services while navigating salary-cap restrictions.
Such an arrangement, if established, would violate the collective bargaining agreement’s prohibition against undisclosed prior agreements.
ESPN salary-cap expert Bobby Marks warned that the potential consequences could be enormous.
“If they are found guilty, there are going to be draft picks stripped and people are going to be suspended indefinitely for a long time here,” Marks predicted.
He pointed to the Minnesota Timberwolves’ infamous Joe Smith scandal in 2000, when the NBA uncovered an illegal agreement involving future compensation and initially stripped Minnesota of five first-round draft picks.
For Milwaukee, similar punishment could be devastating. The Bucks have already entered a rebuilding phase following Giannis Antetokounmpo’s departure to Miami. Their 1-10 start to the 2026-27 season has only reinforced concerns about the franchise’s immediate future.
Losing additional draft capital would significantly complicate their efforts to rebuild around young prospects, while suspensions could destabilize an already embattled front office.
Windhorst specifically raised the possibility that general manager Jon Horst could face disciplinary action. He also suggested that if Horst were to leave the organization, the combination of a struggling roster, limited draft flexibility and potential league sanctions could create one of the least attractive general manager vacancies in decades.
MacMahon was even more pessimistic.
“You call this the danger zone. I call this hell,” he said, suggesting the consequences could affect Milwaukee for years.
Milwaukee is already trying to navigate life after the most successful player in franchise history. Losing draft picks and potentially key decision-makers could turn a difficult rebuilding process into a prolonged organizational crisis.
The Bucks gave Gary Trent Jr. a $64 million contract. If the NBA determines that the deal violated its rules, the true cost could extend far beyond that figure.
