The Milwaukee Bucks waived Damian Lillard on Tuesday, stretching his remaining $113 million in order to sign Myles Turner from the Indiana Pacers. What was once a highly-regarded trade the Bucks agreed to in 2023 is deemed a bad trade two years later.

Damian Lillard tore his Achilles in the first round of the playoffs this year, so regardless of whether he signs anywhere or not, we will not see Lillard on a court for the 2025-26 season, joining fellow Eastern Conference stars Tyrese Haliburton and Jayson Tatum with Achilles injuries. Nobody can help but feel bad for Lillard and these other stars regarding unfortunate Achilles tears. But Haliburton and Tatum aren’t being released; Lillard is.

Two years ago, Lillard was the center of trade rumors after his underwhelming time with the Portland Trail Blazers. The Blazers could not capitalize on Lillard and C.J. McCollum, so Lillard wanted his talents utilized on a championship-caliber team. The Miami Heat were looked at as serious suitors, and rather than pairing Lillard with Jimmy Butler, the Bucks swooped in for Damian Lillard to join forces with Giannis Antetokounmpo.

At the time, everyone heralded this trade for the Milwaukee Bucks and wrote the Bucks in as shoe-ins for the NBA Finals. They also ridiculed the Heat for keeping Tyler Herro and not closing the deal with the Trail Blazers.

Instead, this is the 3-team deal that went down.

• Bucks receive: Damian Lillard, two first-round pick swaps (2028, 2030)
• Trail Blazers receive: Jrue Holiday, DeAndre Ayton, Toumani Camara, 2029 first-round pick
• Suns receive: Jusuf Nurkic, Grayson Allen, Nassir Little, Keon Johnson

At the time, Tyler Herro had just come out of a season averaging 20.1 PPG, 5.4 RPG, and 4.2 APG on 43.9% shooting and 37.8% from three-point range, at 23 years old. In comparison, Lillard had a career-high 32.2 PPG, along with 4.8 RPG and 7.3 APG on 46.3% shooting and 37.1% from beyond the arc. By comparison, even with Lillard being 11-12 years older than Herro, the fans wanted the Heat to capitalize on their window with Jimmy Butler.

People could make the case for Pat Riley’s unwillingness to move off Herro for Lillard was the first domino to fall in Jimmy Butler’s downward spiral with the Heat. But in hindsight, people can make the case that Pat Riley is, once again, a genius.

Two years removed from that trade, the Miami Heat kept Tyler Herro, who just became an All-Star for the first time at 25. Herro has emerged as the best player on the Heat after Jimmy Butler’s departure, and it appears Herro will be a significant piece in the Heat’s future as an organization. As for the Bucks, they traded for Lillard and have nothing to show for it, especially after waiving the 9-time All-Star.

The most significant piece the Milwaukee Bucks gave up was Jrue Holiday. Holiday was a vital part of the 2021 championship team for Milwaukee. Holiday averaged 17.3 PPG, 8.7 APG, 5.7 RPG, and 1.7 SPG in the playoffs that year. Holiday’s defense and leadership catapulted the Bucks to a championship, Milwaukee’s first since 1971.

The Bucks gave up Holiday and struck this deal, hoping Lillard would be the star to help Giannis earn his second championship. Instead, the Bucks were first-round exits both years of Lillard’s time in Milwaukee.

For the Bucks, it’s an experiment that went from bad to worse, from the underwhelming playoff performances, to Lillard’s injury, to waiving him and getting nothing in return. We’re now at the extreme where Chris Haynes is reporting Giannis Antetokounmpo is not happy with Damian Lillard’s exit. The very last thing the Bucks should be doing right now is upsetting their biggest star.

We’ve speculated before that Giannis Antetokounmpo would want to go to a larger market if he left Milwaukee. How poetic would it be if the Lillard transaction from today influenced Giannis to join the Miami Heat.

This could be a day that the Bucks look back on and regret ever making the deal for Damian Lillard.