A Tyler Herro trade that gives the Pistons the help Cade Cunningham needs

The Detroit Pistons made offseason moves to add shooting and open up the floor, bringing in names like Isaiah Joe, John Collins, Gary Harris and Taurean Prince. But the pressure Cade Cunningham faced from defenses during the postseason showed the team also needs another half-court ball-handler, since Daniss Jenkins was a huge help last year but remains the only proven creator behind the MVP candidate.

As Bleacher Report reports, the trade idea has the Pistons landing Tyler Herro, while the Milwaukee Bucks would get Ron Holland, Duncan Robinson and an unprotected 2027 first-round pick. Herro has averaged at least 20.0 points per game in each of the last five seasons and is known for his ability to generate quick offense without the help of an assist; in every season he has scored more than half of his two-point field goals unassisted. Last year, among the Pistons’ highest-minute players, only Cunningham, Jenkins and Caris LeVert had that same large unassisted scoring profile. Herro’s expiring contract, carrying a $33 million salary, limits the risk for Detroit if the experiment doesn’t work, while moving on from Holland could make sense if the organization is committed to Ausar Thompson; the loss of Robinson is expected to be offset by the added shooting volume the Pistons brought in during free agency.

For Milwaukee, the trade makes sense within a rebuild after the Giannis Antetokounmpo era: a 2027 first-round pick is an asset the organization should be stockpiling. Turning Herro into Holland and Robinson appears to be a sound financial decision — Holland is entering the third year of his career and could be extended or retained via restricted free agency in 2028, while Robinson’s contract has one more season and the $15.2 million for 2027-28 is not guaranteed. Holland brings defensive intensity and athleticism that could complement players like Ryan Rollins and recent pick Brayden Burries, letting them run the offense while Holland does the dirty work on defense.

Such a trade would give the Pistons a self-sufficient creator to ease Cunningham’s burden and offer the Bucks the chance to restart with long-term assets, while Herro’s expiring contract minimizes the risk for both sides. According to Bleacher Report, that is why the offer strikes a balance between on-court needs and financial considerations.