The Milwaukee Bucks have an open two-way spot, and that alone makes Rob Dillingham a name worth keeping in the mix.
Dillingham was recently cut by the Charlotte Hornets, and while Milwaukee’s backcourt is already crowded, the upside here is obvious: the Bucks could stash him with the Wisconsin Herd, let him play real minutes, and see whether he can rebuild some momentum. On a two-way, that kind of setup starts to make a lot of sense.
The Herd’s roster has already changed quite a bit this summer. They brought in a new head coach and also moved on from Stephen Thompson, Mark Sears, and Kira Lewis Jr. Those were important pieces for the group last season, which means there are going to be plenty of touches and opportunities available on this version of the team.
That opens the door for a player like Dillingham.
He hasn’t matched the hype that came with being selected eighth overall just a couple of years ago, but the talent hasn’t disappeared. He’s still not even 22, and after being traded twice and cut once, the most valuable thing for him right now is a situation that puts development first. Milwaukee wouldn’t really be able to do that with the main roster, but the G League path could be different.
With the Herd, Dillingham could take on a meaningful role and work on his game in a setting where he’d actually get the ball in his hands. The Bucks have shown they’re willing to reward internal growth when someone earns it, and that makes Dillingham at least worth a serious look. At the very least, he’s an interesting option because he was the eighth pick just two summers ago and showed flashes with the Chicago Bulls near the end of last season.
Of course, this is where the fit gets messy. Milwaukee already has plenty of guards, and the current backcourt depth chart is crowded enough without adding another one. The team also already has two guards on two-way deals in Kam Jones and Cormac Ryan, so bringing in Dillingham would only intensify the logjam.
Still, when the Bucks are deciding how to use that final two-way slot, talent has to come first. Another center would help the depth chart, sure, but if the upside is there, another guard isn’t some roster-breaking mistake. Former eighth overall picks don’t pop up every day, and that alone makes Dillingham a player Milwaukee should at least check in on.
In Other News...
Bucks Suddenly Have A Real Shot In Jalen Duren Drama
Jalen Durens contract situation has turned into one of the more intriguing offseason storylines, and the ripple effects are reaching Milwaukee. After declining a $200 million offer from Detroit, Duren is staring down a looming deadline on a qualifying offer while the Pistons sort through their own internal questions about his place in the roster hierarchy. The presence of a weight clause in Detroits proposal reportedly surprised Duren and his camp, adding another layer to a negotiation that already had plenty of tension.
For the Bucks, the uncertainty matters because they have shown interest in Duren and suddenly have a plausible path to enter the mix if things break the right way. A decision on his future is expected soon, which keeps Milwaukee on the edge of a situation that could shift quickly depending on what Duren and the Pistons do next. For a team always looking for ways to stay in the conversation, this is the kind of development worth watching closely. [Read more 🡒]
Bucks Frontcourt Plan Could Change Myles Turners Role In A Hurry
A frontcourt overhaul may already be taking shape in Milwaukee, and it could have ripple effects for Myles Turner before the season even settles in. According to The Athletics Sam Amick, the Bucks are one of two teams seriously interested in Detroit big man Jalen Duren, a player whose bruising style and interior presence would give Milwaukee a very different look in the paint under coach Taylor Jenkins.
Turners name has surfaced as a possible part of the framework, but Detroit has not engaged in talks, leaving the idea more as a real possibility than a firm negotiation. Still, the fit question is hard to ignore: Durens physical approach would alter how the Bucks think about their frontcourt, and if Milwaukee keeps pressing, this could become one of the more consequential roster watches on the board. [Read more 🡒]
Bucks Are Treating Taylor Jenkins Like Far More Than A New Coach
The Bucks did not make a casual coaching change this summer. By bringing in Taylor Jenkins on a long-term deal to replace Doc Rivers, Milwaukee signaled that it wanted more than a new voice on the sideline. Co-owner Wes Edens made that plain in his comments, pointing to Jenkins successful run with the Memphis Grizzlies and framing the hire as a real commitment to a different direction.
What stands out now is how quickly the message around the team has shifted to accountability and growth. The tone around media day suggested Jenkins is being treated less like a standard first-year coach and more like the centerpiece of a broader reset, one with organizational buy-in behind it. For a Bucks team trying to re-establish its identity, that kind of support matters, and it gives this hire a much bigger feel than a simple replacement at the top. [Read more 🡒]