Another potential Milwaukee Bucks trade with the Detroit Pistons

For two teams that share the same division and play each other often, the Milwaukee Bucks and the Detroit Pistons have been in plenty of conversations during the offseason.

When the Bucks traded Giannis Antetokounmpo and Bobby Portis to the Miami Heat earlier this summer for Tyler Herro, Jaime Jaquez Jr., Kel'el Ware and Kasparas Jakučionis, there was chance that Milwaukee could make another move with its newly acquired pieces. One of those pieces was Herro.

There was a possibility that the Bucks would flip the former All-Star for more assets as they committed to the rebuild, with one of the destinations being the Pistons. That idea slowly deteriorated over the offseason and eventually became an after thought as Milwaukee had just traded for Herro.

Recently, the trade talks between Detroit and the Bucks have started back up with another possible trade with this time involving All-NBA player, Jalen Duren. With Duren and the Pistons having a standoff about his contract situation, it was reported that Milwaukee had serious interest in the 22-year-old if the two sides couldn't reach a deal.

The Milwaukee Bucks have serious interest in Jalen Duren, per @sam_amick

“Still, Duren’s confidence is born out of the fact that his market for next summer looks quite robust. As The Athletic previously reported, the Sacramento Kings have signaled a willingness to pay him a… pic.twitter.com/dIIG0W8Y0V
— NBACentral (@TheDunkCentral) September 21, 2026

If those two conversations weren't enough, Bleacher Report's Grant Hughes recently proposed a potential trade idea involving the two teams once again, and at the center of it was Herro.

This would make the East interesting 👀

Full trade here: https://t.co/p3I2ABuEwe pic.twitter.com/yCVbZWVDsO
— Bleacher Report (@BleacherReport) September 25, 2026

Detroit Pistons Acquire: Tyler Herro

Milwaukee Bucks Acquire: Ron Holland, Duncan Robinson, 2027 unprotected first-round pick

From the Pistons' perspective, it clearly makes sense as they need another scorer to help take off the stress from superstar Cade Cunningham, and with a player like Herro who averaged at least 20 points per game in the last five season, it would be a good fit.

Hughes wrote, "Last year, Cunningham, Jenkins and the departed Caris LeVert were the only players ranking among Detroit's top 10 in minutes who joined Herro in making most of their twos without an assist. That kind of self-sufficient bucket-getting skill is exactly what the Pistons need to take the pressure off of Cunningham while also maximizing the value of their setup-dependent shooters."

He also explained that since Herro is on an expiring deal, it wouldn't as big of a risk if things don't work out.

For Bucks side, he wrote "Rebuilding in the first year of its post-Giannis Antetokounmpo era, Milwaukee should be in the business of hoarding as many future first-rounders as possible. It lands one here in exchange for Herro. The Bucks might put some extra hometown value on the Wisconsin native, but they also need to be wary of committing to him on a new contract. Turning him into Holland and Robinson makes more financial sense for a couple of reasons."

If Milwaukee is presented with the right package, then I think exploring Herro isn't the craziest idea in the world since he's on an expiring deal and the Bucks would like to get more draft capital for the future.

However, this package in my opinion isn't the right one. The Pistons are in desperate need of another scorer espically what happend in this year's playoffs and who they lost in free agency.

Detroit lost its second-leading scorer in playoffs to the San Antonio Spurs this offseason after he averaged 18.1 points per game during the the postseason. After Harris, Robinson was third at 11.8 and Duren at 10.2 points per game.

The Pistons added John Collins, Ebuka Okorie and some shooters such as Isiah Joe and Taurean Prince, but there's still a lack of shot creation and scoring especially if Duren gets potentially moved.

Herro fixes both of those problems for Detroit and would make an immediate impact. I understand that the Bucks are in a spot where they don’t look like they’re going to compete competitively with the current roster, but to essentially ask to give up a team’s best player for one first-round draft pick and two role players without even playing a game yet, I don't think it's nearly enough value for a player of Herro's caliber.

Though only 21 years old, Holland only averaged 8.2 points, 4.0 rebounds and 1.2 steals on 43.2% shooting from the field and 25.3% from the 3-point last season, while Robinson, who is mainly a sharpshooter, averaging 12.2 points per game on 41% shooting from the field last year, don't provide enough production for the Bucks

If Detroit added some more draft capital to the trade then I think it would become a more attractive deal for a proven scorer like Herro, but even though Milwaukee might be a team projected to finish near the bottom of the conference, I don't think it's a fair trade.

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