Winning an NBA title and sustaining championship success is difficult. There has not been a repeat champion in each of the last seven postseasons. The last team to accomplish that feat was the Warriors in 2017 and 2018. 

In 2021, the Milwaukee Bucks won the NBA Finals. Since then, the team has one playoff series win. Milwaukee traded for Damian Lillard ahead of the 2023-24 season, and they have three playoffs win to show for it. On Tuesday, the Bucks shockingly waived Damian Lillard and stretched out the remaining $113 million on his deal. ESPN’s Tim MacMahon went on First Take Wednesday morning and called the Lillard trade “a complete disaster.”

The Bucks turned their back on Damian Lillard

“The Damian Lillard trade was a complete disaster.” 😳

—@espn_macmahon on the Bucks having to pay Lillard while not possessing all of their first round picks 😅 pic.twitter.com/k6haOZbizN

— Get Up (@GetUpESPN) July 2, 2025

Milwaukee waiving nine-time all-star Damian Lillard is a set of unfortunate events. When the 34-year-old tore his left Achilles in the 2025 playoffs, the Bucks’ 2025-26 trajectory took a major hit. Damian Lillard has been a key player for Milwaukee over the last two seasons. The Bucks hoped Lillard could be that PG to help the team reopen that championship window. That was far from the case in Lillard’s tenure with the Bucks.

He started all 131 games he played for Milwaukee and was voted an all-star in 2024-25. Lillard averaged 24.9 points, 4.1 rebounds, 7.1 assists, and 1.2 steals per game. Damian Lillard is set to miss the entire 2025-26 season with an Achilles injury. That left Milwaukee to make a tough decision and cut the veteran point guard this offseason.

The Bucks will owe Damian Lillard over $22M a year for the next five years.

That will count towards their cap space for the next FIVE years.

Madness. 🤯 pic.twitter.com/ovPN7b8RHy

— Legion Hoops (@LegionHoops) July 1, 2025

The Bucks had to waive Damian Lillard so they could sign free agent big man Myles Turner. He is part of Milwaukee’s plan to keep Giannis Antetokounmpo happy. However, Bleacher Report’s Chris Haynes reported that Giannis was “not pleased” with the team’s decision to waive Lillard. That is why ESPN’s Tim MacMahon called the Damian Lillard trade “a complete disaster.”

MacMahon noted that the team still hasn’t paid off their first-round picks from the Jrue Holiday trade. Their 2027 first-round pick is owned by the New Orleans Pelicans. On top of this, the Bucks now owe Damian Lillard $22.5 million per year over the next five seasons. That’s a massive hit on their salary cap. All of this was done to sign Myles Turner, an upgrade from Brook Lopez. However, it’s hard to believe Turner was the missing piece holding back the Bucks from being contenders in the East.

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