The 10 Wildest what-if scenarios in Milwaukee Bucks history
By Tyler Watts
5. Bucks draft Jrue Holiday over Brandon Jennings
Holiday helped push Milwaukee to a championship in 2021. They were close before he arrived, but adding a stout defender and playmaker took the Bucks to new heights. With him, the Bucks won a title, lost a seven-game series to the eventual Eastern Conference champion Celtics, and were bounced in the first round as Giannis missed time. Milwaukee was a feared team, even when things did not work as planned.
Holiday won his second ring in 2024 with the Celtics and again proved he can play a crucial role on a championship team.
Imagine if he spent his entire career with the Bucks. Holiday was the 17th overall pick in the 2009 draft by the Philadelphia 76ers, but Milwaukee that selected Brandon Jennings at ten. If they chose the right guard, Holiday could have been a Buck from the beginning. It certainly would have changed his story and years later saved Milwaukee a ton of draft capital.
2009 was the draft of point guards. Stephen Curry, James Harden, and Rick Rubio went before Jennings. The Bucks also missed on Jeff Teague, Ty Lawson, Darren Collison, and Patrick Beverley in this class. All have better career value over replacement players (VORPs) than Jennings.
It is fun to think about how Holiday would have changed things back in 2009 more than a decade before he actually arrived.