The 10 Wildest what-if scenarios in Milwaukee Bucks history
By Tyler Watts
9. Bucks don’t make the trade for Dame
The Damian Lillard saga dominated headlines in the 2023 offseason. He wanted to leave Portland and his desire was to land in Miami. The Trail Blazers were not interested in the Heat’s package, which opened the door for Milwaukee to jump in.
The Bucks gave up Jrue Holiday, Grayson Allen, a 2029 first-round draft pick, and two first-round swaps to land Dame. It was an all-in move as Milwaukee tried to show Giannis it would do whatever it took to put another title-winning roster around him.
The bold move quickly worsened as the Blazers flipped Holiday to the rival Celtics. Now, one of the best perimeter defenders in the world and their championship point guard is in their direct path to glory. Sadly, Milwaukee never made it far enough to face Boston. The Celtics won the championship with Holiday filling a key role throughout.
What if the Bucks don’t trade Jrue for Dame? Milwaukee still has the firepower to compete for a championship and Boston never gets Holiday. It may have shifted the balance of power and prevented the Celtics from dominating their way to a title in 2024. There is no guarantee the Bucks are better, but Boston certainly would be worse if this trade never happened.