When the NBA stripped the Minnesota Timberwolves of multiple draft picks in 2000 for Joe Smith’s infamous ‘under-the-table’ contract agreement, it sent a clear message that salary-cap circumvention would not be tolerated. More than two decades later, another deal has sparked similar questions, with ESPN insider Shams Charania reporting that the league has officially launched an investigation into something similar.

According to Charania, “The NBA is probing the signed $64 million free-agent deal for Gary Trent Jr. with the Milwaukee Bucks, per a league spokesperson.”

The investigation is on whether Milwaukee and Trent’s representatives had a banned pre-arranged agreement before the guard signed consecutive below-market contracts with the franchise. Trent initially joined the Bucks on a veteran minimum deal before signing a two-year, $7.5 million contract. After Milwaukee acquired his Bird Rights, the team rewarded him with a fully guaranteed four-year, $64 million extension, prompting league-wide scrutiny.

NBA insider Marc Stein hinted that league intervention could be coming before the investigation became official. Writing on his Substack, Stein noted there had been “copious amounts of external noise that it is, at the very least, quite curious in the wake of the two low-dollar deals that Trent … signed with them and how he performed in 2025-26.”

The size of the contract was always going to raise an eye because Trent had one of the least productive seasons of his career. The 27-year-old averaged just 8.1 points while shooting 38.7% from the field and 36.0% from the 3-point mark, his lowest scoring average since his rookie season. Despite those numbers, Milwaukee committed $16 million annually to retain him.

The Athletic’s Sam Vecenie was among the loudest critics of the agreement. “The NBA should probably take a look at what is a truly nonsensical contract here given that Trent just averaged 8 PPG and shot 39% from the field in 22 minutes per game last season.” He also questioned the unprecedented nature of the deal, asking, “What other player in the past has agreed to sign for the minimum one year, gone on to have his worst season in seven years where he was a below-average player by any standard, and then received 5x as much money in free agency the following year?”

For now, the NBA has not accused either the Bucks or Trent of any wrongdoing. The investigation will determine whether Milwaukee simply used Trent’s Bird Rights within the rules or whether the forbidden handshake agreement existed before the lucrative payday.

What’s Next for Gary Trent Jr. and Milwaukee?

The NBA’s next step will be gathering evidence. League officials are expected to review communications between the Bucks, Gary Trent Jr, and his team while examining whether there was any pre-arranged promise before the guard signed consecutive below-market contracts with Milwaukee.

One detail that could prove significant is Charania’s report that “at least one team” explored a sign-and-trade for Trent “at around the same type of number.” If the NBA confirms that interest was genuine, it could strengthen Milwaukee’s argument that Trent’s $64 million contract reflected his market value rather than a predetermined agreement.

NBA reporter Grant Afseth’s reaction to that was different, tweeting. “Having documented interest, whether truly legitimate or not, is advantageous in the event of an NBA investigation.” He also questioned why the interested team has never been identified. “Not naming the supposed interested team’s name is suspicious at a minimum. It suggests an executive did not want their team’s name attached to the reported interest, which should raise questions about whether the interest is legitimate or was done as a favor.”

Should the NBA find no evidence of salary-cap circumvention, the investigation would likely conclude without further action, leaving Trent’s contract untouched.

However, if investigators uncover proof of a prior agreement, the Bucks could face significant penalties, including fines, loss of draft picks, executive discipline, or other sanctions available under the league’s Collective Bargaining Agreement.

Joe Smith’s 2000 case shares similarities. In both cases, a player signed below-market contracts before eventually receiving a substantially larger deal after the team secured Bird Rights.

But the key difference is the evidence.

The NBA found documents detailing a back-room deal in the Joe Smith case and penalised Minnesota with the loss of five first-round draft choices, a $3.5 million fine and the suspension of owner Glen Taylor.

No such evidence has emerged in the case of Trent.

Instead, the current line of questioning is ‘circumstantial’ questions about when the contracts came down, Trent’s disastrous run last season before he inked the deal, and whether Milwaukee’s $64 million commitment was indicative of real market demand. Or if there was an arrangement prearranged.