After leaving Portland to join Milwaukee only to rejoin Portland two years later, Damain Lillard learned that the grass isn't always greener elsewhere. The guard himself acknowledged just how out of place he was in Milwaukee during a press conference with the Trail Blazers, letting it be known just how hard it was for him to find his footing with the Bucks.
"It never felt right not being home. Through it all, I found my way back.”
Lillard says what everyone in Milwaukee knew
Damian Lillard never initially wanted to join the Milwaukee Bucks. When he requested a trade back in the summer of 2023, the only team he wanted to join was the Miami Heat. When they wouldn't cough up an adequate package, Milwaukee snuck into the conversation and pushed their chips all-in to get the guard. Lillard accepted, though it wasn't his ideal landing spot.
It's clear that the guard, who had spent his entire NBA career in Portland to that point, never quite made himself at home in Milwaukee. He spoke about missing family and those close to him. Prior to him being waived to create the necessary cash to sign Myles Turner, Lillard was reportedly going to spend most, if not all, of next season rehabbing his torn Achilles away from the team in Portland.
It was never any secret that Portland was on his mind, which is why it wasn't shocking to Bucks fans paying attention when he ultimately inked a three-year deal there after being cut by Milwaukee. Now, Lillard can return home, rehab for the entire season, and be close to those he missed so much when he was in Milwaukee for those two seasons. It's a great move for him.
No one ever wanted to acknowledge how clear it was that he missed Portland, hoping that an opportunity to chase a championship would help him feel welcome. It didn't entirely.
From the Milwaukee Bucks' point of view, they cannot be blamed for the Lillard trade not working out. They had an opportunity to pair a top 75 player with Giannis Antetokounmpo, and they pounced on it, as just about every other franchise would do if they had a realistic pathway. It didn't work out, and that is just how things happen sometimes.
None of this is to condemn Damian Lillard. He missed his family. No one can blame him for that. He left everything out there for the Milwaukee Bucks, coming back to play this past season after overcoming a blood clot in historic fashion. That will always be admirable. In the end, Lillard got what he wanted, while the Milwaukee Bucks patched a major weakness at center. Win. Win.
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