The Milwaukee Bucks have one of the most storied histories in the NBA.
Since the franchise’s inception in 1973, the city of Milwaukee has been spoiled with some legendary NBA figures and are currently enjoying a tremendous run of success behind franchise cornerstone Giannis Antetokounmpo.
While much of the Bucks’ success is rightfully attributed to Giannis, Milwaukee has a tremendous “man behind the curtain” making brilliant moves in general manager Jon Horst. Since taking over in 2017, Horst and the Bucks have not missed the playoffs, have appeared in two Eastern Conference Finals, and even brought home a championship in the 2020-21 season.
While Horst didn’t draft Giannis or fellow All-Star Khris Middleton, he brought in Jrue Holiday, Brook Lopez, and many others through free agency who were instrumental in their recent championship core and future title aspirations.
Although the Bucks have been spoiled by great front office work over the past decade, that hasn’t always been the case. Like every other franchise, Milwaukee has experienced plenty of free agent signings or draft picks who flamed out or got shipped out only to make the most of greener pastures once they donned another uniform.
Some certainly hurt worse than others, but every one of them left the same question: what could have been?
Players the Milwaukee Bucks gave up on way too soon: No. 5 – Gary Payton II
While most didn’t learn the name Gary Payton II until his stint with the Golden State Warriors, which included a championship run, one of Payton’s earliest stops was in Milwaukee.
The former Oregon State star’s first NBA minutes actually came in a Bucks jersey. While he was initially signed by the Rockets as an undrafted free agent out of college, he never suited up for Houston and spent the majority of his time with their G-League affiliate.
Payton ended up being waived twice in the span of a single season with the Bucks but showed flashes of the player he would become. While he didn’t bring much on the offensive end, he showcased his trademark, junk-yard dog defensive intensity harassing opposing guards.
After getting cut by the Bucks in 2017, Payton was mostly a journeyman unable to find a secure home until he reached Golden State in 2021. On the Warriors’ title team in 2021-22, Payton played major minutes off the bench and was a key defensive stopper touting a defensive rating of 102.6 according to StatMuse.
While there’s no guarantee Payton would’ve flourished the way he did had Milwaukee held onto him, you have to imagine that the Bucks’ brass can’t help but wonder what a defensive backcourt of Jrue Holiday and Payton would’ve looked like.