The Milwaukee Bucks and Detroit Pistons have already been circling each other plenty this offseason, and Tyler Herro keeps landing in the middle of the conversation.
That wasn’t the first Bucks-Pistons idea to surface, either. Earlier this summer, Milwaukee sent Giannis Antetokounmpo and Bobby Portis to the Miami Heat in a deal that brought back Herro, Jaime Jaquez Jr., Kel'el Ware and Kasparas Jakučionis.
Once Herro got to Milwaukee, there was immediate buzz that the Bucks could flip him again as part of their rebuild, with Detroit floated as one possible landing spot. That possibility faded for a while, but it’s back in the mix now.
The latest round of chatter started with Jalen Duren. With Duren and the Pistons locked in a contract standoff, reports said Milwaukee had serious interest in the 22-year-old if Detroit couldn’t get a deal done. From there, Bleacher Report’s Grant Hughes took the idea a step further and built a Herro-centered trade proposal between the two teams.
Under Hughes’ framework, the Bucks would receive Ron Holland, Duncan Robinson and a 2027 unprotected first-round pick.
From Detroit’s side, the logic is easy to see. Cade Cunningham needs another scorer next to him, and Herro has been a 20-point-per-game guy in each of the last five seasons. Hughes pointed to Herro’s ability to create his own shot as the exact kind of skill the Pistons are missing.
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 noted that Herro’s expiring contract lowers the risk if the fit doesn’t click.
For Milwaukee, Hughes argued the appeal is tied to the rebuild. 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."
Even with that logic, the deal feels light for a player like Herro. Detroit needs scoring, badly, especially after what happened in the playoffs and with the departures it had in free agency.
The Pistons lost their second-leading scorer in the playoffs to the San Antonio Spurs this offseason after he averaged 18.1 points per game in the postseason. After Harris, Robinson was third at 11.8 and Duren at 10.2 points per game.
Detroit did bring in John Collins, Ebuka Okorie and shooters like Isiah Joe and Taurean Prince, but the roster still lacks enough shot creation, and that problem only gets worse if Duren is moved.
Herro would solve that. He would also give Detroit an immediate boost. But from Milwaukee’s perspective, asking the Bucks to give up their best player for one future first and two role players, before those pieces have even played a game together, doesn’t feel like enough.
Holland, though only 21, averaged 8.2 points, 4.0 rebounds and 1.2 steals while shooting 43.2% from the field and 25.3% from 3-point range last season. Robinson, meanwhile, put up 12.2 points per game and shot 41% from the field. Neither one brings enough back on its own to justify moving Herro.
If Detroit added more draft capital, the conversation would look different. As it stands, though, this one doesn’t feel like a fair price for a proven scorer.
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