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.
Players the Milwaukee Bucks gave up on way too soon: No. 4 – Charlie Villanueva
Charlie Villanueva was initially drafted by the Raptors in the 2005 NBA Draft. However, he didn’t start to make waves in the NBA until he was traded to Milwaukee months before his sophomore campaign.
In his three seasons with the Bucks, he built up steadily and steadily until he finally had his breakout year in the 2008-09 season. He averaged 16.2 points and 6.7 rebounds per game on nearly 45 percent shooting from the floor.
That year would unfortunately be his last in Milwaukee.
Former general manager John Hammond did not seem to prioritize Villanueva. Instead, he allowed the forward to become an unrestricted free agent while the Bucks decided to keep Ramon Sessions and Ersan Illyasova instead on restricted contacts. Bucks’ management also believed they had something in rookie Brandon Jennings (they did not).
Villanueva went on to have a productive career as a role player with the Pistons and Mavericks, respectively. However, he never again reached the highs of his 2008-09 season with the Bucks. You have to wonder if both parties regret that decision all of these years later.
Players the Milwaukee Bucks gave up on way too soon: No. 3 – Ricky Pierce
Ricky Pierce was one of the most dynamic sixth men in the league during his run with Milwaukee Bucks during the 80s. He was a microwave scorer who consistently averaged over 15 a game for a talented Bucks team and was as big a part as any of Milwaukee’s success during that timeframe.
His best season was by far during the 1990-91 campaign, where he averaged 22.5 points on nearly 50 percent from the field. The 1990 season led to his first and only All-Star selection and also happened to be his last year in Milwaukee as he was dealt to the Seattle Super Sonics midseason in a deal for Dale Ellis. Ellis played just 102 regular season games with the Bucks after the move before rejoining the team during his final season in 1999-2000.
The trade almost instantly led to the collapse of the Bucks who, in turn, spent the next eight seasons under .500 until Ray Allen arrived in the 1999-2000 season.
While Pierce had done plenty of time with the Bucks, the franchise has to feel they could’ve at least remained competitive had they kept him around.
Players the Milwaukee Bucks gave up on way too soon: No. 2 – Ray Allen
Ray Allen’s departure from the Milwaukee Bucks is one of the most infamous moments in Milwaukee sports history.
While Milwaukee didn’t necessarily “give up on him” per se, management still took the side of head coach George Karl over Allen in a feud that led to the trade. Many saw the trade as a decision that set the Bucks back a decade and former long-time owner Herb Kohl said it was the team’s “most unfortunate moment” in 2016.
Allen was a rising superstar with the Bucks averaging roughly 22 points in his final three years in a Bucks uniform before being traded to Seattle during the 2002-03 season. By the time he was traded, he was shooting roughly 44 percent from the field and had years where he was shooting as good as 43 percent from behind the arc.
After the departure of Ray Allen, the Bucks practically wandered through the wilderness until the rise of Giannis Antetokounmpo in the mid-2010s. Who knows what would’ve happened had the Bucks opted to side with Allen? But it certainly couldn’t have been as bad as it became.
Players the Milwaukee Bucks gave up on way too soon: No. 1 – Tobias Harris
Current 76ers’ forward Tobias Harris spent his first three years in the NBA as a part of a rebuilding Milwaukee Bucks franchise. While he was drafted by Charlotte with the 19th pick in the 2011 NBA Draft, he was traded on draft night to Milwaukee.
Harris struggled with playing time as a member of the Bucks, mostly only showing flashes of the player he would eventually become. In his two-and-a-half seasons with Milwaukee, he averaged roughly five points and 2.5 rebounds per game.
In February of 2013, Harris was traded to the Orlando Magic. With an increased role, he almost immediately showed his full potential. In his first year with the Magic, his points per game average skyrocketed up to 17.3 on 45.3 percent from the field. His rebounds per game also increased to 8.5. He was a completely different player, and those numbers stayed steady for the entirety of his tenure with the Magic.
Harris has only gotten better since then while making more pit stops with the Detroit Pistons and the Los Angeles Clippers, respectively. While he has gotten a little older, he is still a highly productive role player currently with the Philadelphia 76ers.
Harris just needed to find the right place to shine. Unfortunately, that place was not in Milwaukee.
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