The Gary Trent Jr. deal may have faded from the headlines for a moment, but the concern around Milwaukee has not gone anywhere. The NBA’s investigation still hangs over the Bucks, and for a fan base trying to look ahead to a younger reset, the possibility of punishment remains the part nobody can quite shake.
That fear sharpened after Draymond Green laid out just how ugly the fallout could get if the league comes down hard. On The Draymond Green Show, the Golden State forward drew a direct line between Milwaukee’s situation and the kind of punishment that hit the LA Clippers.
"Unlike Steve Ballmer who has a team in Los Angeles, if the Milwaukee Bucks lose five first-round picks they can never be good for 20 years," Green warned. "This would really set the Milwaukee Bucks back and I think if this was to happen, I think the Bucks owner would sell... if Milwaukee Bucks lose five first-round picks, they can never be good for 20 years so I’d think you’d see the owner sell the team. They’re going to be trash-like they can’t rebuild, no free agent is going to Milwaukee, they’ll have to pay a fourth-tier player max money to come to Milwaukee," Green said.
That is the nightmare scenario still floating over Milwaukee’s offseason. The league is looking into the Bucks’ four-year, $64 million deal with Trent, a contract that stood out immediately because it went to a reserve guard coming off an 8.1-point season on 38.7 percent shooting. That kind of number is exactly why the move drew suspicion in the first place, with questions swirling around salary-cap circumvention and whether there was more to the agreement than what was on the surface.
Green’s larger point is hard to ignore: not every franchise can absorb a crushing punishment the way a big-market team might. The Clippers could take a hit and still lean on owner wealth, a new arena, and the pull of Southern California. Milwaukee does not have those built-in escape hatches.
The Bucks live and die on smarter roster work, player development, and whatever draft capital they can stockpile. That is why the stakes around their future picks matter so much. The post-Giannis rebuild, including the push toward building blocks like Brayden Burries and Nate Ament and the effort to keep future picks from Miami, depends on having those chances in the draft over the next several years.
If the league were to take five first-round selections, the damage would go far beyond one bad headline. It would strip away the Bucks’ ability to draft, weaken their trade flexibility, and leave them with even less room to maneuver in free agency. As Green put it, that kind of punishment leaves a team stuck overpaying lesser players just to stay afloat.
For Milwaukee, that is why the investigation matters so much. The Trent deal might still end up helping the team. But until the league finishes its work, the worst-case outcome remains very much on the table.
In Other News...
Bucks Must Decide If This Former Top Pick Is Worth The Backcourt Squeeze
The Bucks are still sorting through the edges of their roster, and the open two-way slot has become a place where upside matters as much as immediate fit. Rob Dillingham, who was recently cut by the Hornets, is one of the names in the mix, and his appeal is easy to see for a team that is always looking for another guard who can eventually grow into a larger role. With the Wisconsin Herd also going through roster changes, Milwaukee has a development pipeline that could give a young player a real chance to settle in and improve.
Still, the question is whether the Bucks can afford to add another backcourt piece without crowding the room even more. Their guard group is already tight, so any move for Dillingham would have to be justified by the long view rather than short-term minutes. For a team trying to balance depth, development and fit, the decision is less about whether the talent is interesting than whether the squeeze in the backcourt is worth it. [Read more 🡒]
Kevin Porter Jr. Wants To Stay But Bucks Face A Backcourt Squeeze
Kevin Porter Jr. has already made his first offseason choice, picking up his player option to stay with the Bucks after a season interrupted by injuries. It is an outcome that keeps him in Milwaukee for now and lines up with his stated desire to build his career there, giving the team another backcourt piece to sort through as it plans for the months ahead.
The complication is what comes next. Tyler Herro and Ryan Rollins are also on track to be free agents next year, leaving Milwaukee with a crowded and potentially fluid guard picture as it weighs roster priorities and future flexibility. Porter could end up as part of that mix in a veteran presence role, or he could become a name to monitor if the Bucks decide a different backcourt alignment makes more sense. [Read more 🡒]
Kevin Porter Jr. Could Quietly Swing The Bucks Backcourt Plan
Kevin Porter Jr. spent 38 games with the Bucks last season and turned in some of the best production of his career, enough to keep him in the conversation as Milwaukee sorts out its backcourt plans for the year ahead. At media day, Porter said he is healthy entering the upcoming season, an important starting point for a player whose path with the team has already shown signs of fit and upside.
The next step may be less about where he stands on the roster and more about how the Bucks use him. The coaching staff is considering Porter as a bench option to run the second unit, a role that could put the ball in his hands more often and give him the freedom to drive his numbers even higher. For a team looking to sharpen its guard rotation, that kind of quiet adjustment could end up mattering more than it first appears. [Read more 🡒]