This past offseason, the Milwaukee Bucks overhauled their roster, choosing to pivot in the aftermath of Damian Lillard's disastrous Achilles tear. Always on a timer especially with Giannis Antetokounmpo set to enter free agency in 2027, the Bucks decided to move on from Lillard, waiving and stretching the hundreds of millions left on his contract, so they could have the requisite space to bring in Myles Turner to try and remain semi-competitive.

This paved the way for Lillard to return to his former team and longtime home Portland Trail Blazers in free agency. And on Monday night, Lillard returned to Fiserv Forum for the first time since being waived by the Bucks, with the Blazers visiting. And the Bucks, even though Lillard only played two seasons for the team, gave him a tribute video thanking him for all his contributions as they tried to fight for a title in the Cream City.

It's safe to say that the Bucks' gambit for Lillard did not work out. They traded away Jrue Holiday in the Lillard deal, and this eventually paved the way for Holiday to join the Boston Celtics, the team that won a title in 2024. Meanwhile, the Bucks lost in the first round in both of their playoff runs with Lillard on the team.

But at the end of the day, the Bucks deserve credit for throwing caution to the wind and going for it. It was just a shame that the Lillard-Antetokounmpo pairing did not work out.

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Bucks are reeling amid Giannis Antetokounmpo's injury

Milwaukee Bucks forward Giannis Antetokounmpo (34) stands on the court in the first quarter against the Cleveland Cavaliers at Rocket Arena.
David Richard-Imagn Images

The Bucks are more reliant on Antetokounmpo than ever now that their key shot creators in the past, Lillard, Holiday, and Khris Middleton, are all gone. Ryan Rollins has emerged as a long-term keeper for Milwaukee, but the team around them hasn't been great. With Antetokounmpo nursing a groin injury, the Bucks have struggled, and they've now lost five straight after taking a 115-103 loss to the Blazers on Monday.

Antetokounmpo will have to return soonest; the Bucks are now below .500, and considering how dire their cap and draft pick situations are, they're going to have to win at all costs.