The Milwaukee Bucks can't be accused of sitting on their hands when faced with the need to build a better product around Giannis Antetokounmpo. Unfortunately, they've miscalculated and misfired on multiple occasions during those retooling efforts.
No trade has proven more disastrous for the Bucks than the ill-fated decision to part ways with Jrue Holiday in 2023.
Holiday played three years with the Bucks, helping to transform the identity of the franchise and ultimately win the club's first title in 50 years. Unfortunately, two early exits from the playoffs had Milwaukee set on drastic changes—and thus, the decision to trade Holiday for Damian Lillard took hold.
Unfortunately, just two years after trading Holiday for Lillard, the Bucks waived their All-NBA acquisition to create space to sign Myles Turner.
Just in: The Milwaukee Bucks are waiving Damian Lillard and stretching the remaining $113 million on his contract in order to acquire Myles Turner, sources tell ESPN. Lillard's two seasons in Milwaukee come to an end as he rehabilitates a torn Achilles tendon. pic.twitter.com/eg1D1TMFM6
— Shams Charania (@ShamsCharania) July 1, 2025
In turn, Milwaukee will be paying Lillard $22 million over each of the next five seasons to not play a single minute for the franchise.
The Bucks will owe Damian Lillard over $22M per year for the next FIVE years 😳
— Yahoo Sports (@YahooSports) July 1, 2025
This is the largest waive and stretch in NBA history. pic.twitter.com/dCNOc8y89c
Suffice it to say, Milwaukee's decision to trade Holiday will go down as one of the most regrettable decisions in franchise history.
Bucks' decision to trade Jrue Holiday leads to waiving Damian Lillard
In three years with the Bucks, Holiday racked up accolades and solidified his reputation as one of the best two-way guards of his era. He earned All-Star honors in 2022-23, secured All-Defense honors during each of his three seasons with the team, and played a key role during the run to the 2021 title.
Holiday finished the 2021 NBA Playoffs averaging 17.3 points, 8.7 assists, 5.7 rebounds, 1.7 steals, and 1.9 three-point field goals made per game.
Despite his endless heroics, including a 27-point and 13-assist eruption in Game 5 of the 2021 NBA Finals, Holiday was traded—mere months after making the All-Star Game. He ended up with the Boston Celtics, with whom he only strengthened his résumé and place in Association history.
Holiday won a second career championship during his first season with the Celtics, securing his sixth All-Defense nod during that same campaign.
As for Milwaukee, they lost in the first round of the playoffs in each of Lillard's two seasons with the franchise. He's by no means to exclusively blame for such developments, especially when one considers the fact that he battled deep vein thrombosis and tore his Achilles tendon in 2024-25.
Unfortunately, the legacy of a trade is typically what it resulted in—and for Milwaukee, it's been a catastrophic step backward.