As soon as Gary Trent Jr’s new deal was reported on Saturday, scrutiny emerged. After declining his player option, the Milwaukee Bucks offered him five times that value, and that too for four guaranteed years. Since then, reports have emerged that the NBA could look into the deal, and Shams Charania has shed light on how it is perceived around the league.

“So Shump, there are a few factors with the G Trent deal,” Charania said on Shump Street with Iman Shumpert. “One is you saw a couple years in a row where Gary Trent Jr. took the minimum, and that certainly raised eyebrows around the league. Because at that point, his play — especially coming off the playoffs — not this past season but the 2025 playoffs — I believe he averaged close to 15, 16, 17, 18, 19 points a game and shot 50-plus percent from three in the playoffs against the Pacers. And he took a minimum the next year, and so there was a school of thought that he had potentially better offers there that summer but he decides to sign for less.

“And certainly, there’s a lot of people raising their eyebrows around the league at this deal that was completed over the weekend between the Bucks, Gary Trent, and his agent Rich Paul. And so it is something that everyone around the league has raised their eyebrows on. But I can say there was at least one team that was poking around a potential sign-and-trade at around the same type of number. It didn’t form, it didn’t happen, but there was a team that was looking at it.”

He added, “Does that mean that his value is at that level? Because sign-and-trades are totally different. Technically, the free agency market — the salary offer — wasn’t out there just in unrestricted free agency, potentially for Gary Trent. And so I definitely think, given the production, given the way he played last year, certainly there’s a ton of people with their eyebrows raised. But listen, for Gary Trent — after the year he had — four years, $64 million contract agreement. I mean, certainly a great deal for him.”

On paper, the 27-year-old earning $64 million on a four-year deal shouldn’t raise any flags. But the manner in which previous deals for Gary Trent Jr. took place, the questions being raised are valid. Let’s not forget that last season he had his worst scoring efficiency since his rookie season. His role diminished, and this year, the Bucks have a plethora of options in the backcourt.

Most free agents aren’t getting more than one fully guaranteed season on deals this offseason. Trent got four at an astronomical value. Initially, in 2024, the one-time NBA champion signed on a one-year deal for the league minimum. Since the Bucks were a second-apron team at the time, it was the only available option.

But he re-signed on a two-year deal before last season, worth a manageable $7.5 million, despite production value that demanded more. Reports indicate that it allowed the Bucks to preserve early Bird eligibility for 2026, allowing them to spend over the cap. Netizens quickly drew similarities to the Joe Smith-Timberwolves situation.

Smith reportedly signed three consecutive short-term, below-market deals from 1996 to 1999. Thus, Minnesota had the Bird rights and later offered a seven-year, $86 million extension. But a secret agreement came to light that promised a big payday but violated NBA rules against circumvention.

The Wolves had to pay a $3.5 million fine, the contract was void, and the removal of five picks was initially imposed. So, the Gary Trent Jr. deal could also come under scrutiny.

Even ESPN’s veteran reporter, Tim MacMahon, stated, “If I was Adam Silver, and I’m some of those head honcho’s in the league office, i’d sniff around.”

But NBA insider Marc Stein revealed why Commissioner Adam Silver and his office are currently quiet.

“The deal has not yet been formally announced by the Bucks, which I’m told is among the reasons that the league office has issued no official response to requests for comment on the signing amid 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 (repped by the aforementioned Paul’s Klutch Sports agency) signed with them and how he performed in 2025-26,” wrote Stein.

It’s true the deal was reported on Saturday, but the team has not confirmed it with an official statement. It seems once the deal is official, the problem for the Bucks and Gary Trent Jr. may begin.