Damian Lillard identifies the darkest time of his Bucks tenure

It's Sept. 27, 2023 and the NBA season is less than a month away. The Milwaukee Bucks just came off an embarrassing upset in the first round of the playoffs, losing to the No. 8 seeded Miami Heat four games to one.

Milwaukee became the sixth No. 1 seed in NBA history to lose in the first round to a No. 8 seed in the opening round, and looked to make some changes. The first change started just eight days after the defeat, and the Bucks fired their head coach Mike Budenholzer. After hiring Adrian Griffin in June, Milwaukee would make a blockbuster move by trading for future Hall of Famer, Damian Lillard in a three-team trade to pair with Giannis Antetokounmpo.

The trade would break up the core that brought a championship to the city for the first time in 50 years and hoped the dynamic duo of Antetokounmpo and Lillard would get them back to where they were just a few a years ago.

It was a chaotic first year for Lillard and the Bucks, as they would fire Griffin after a 30-13 record and replace him with Doc Rivers who would go 17-19 for the rest of the season. Milwaukee would make the playoffs as the No. 3 seed and would lose to the Indiana Pacers in six games as Antetokounmpo missed the entire series due to a calf strain.

The Bucks would return to the playoffs the next year as No. 5 seed, but would lose to the Pacers once again in the first round in five games this time. Like the year before, Milwaukee had another significant injury, this time to Lillard as he suffered a left Achilles tear during the first quarter of Game 4.

A devastating injury for Lillard, and things would go from bad to worse for him as the organization waived him only a few months later. It's been over a year since the Bucks waived him and he's now preparing to finally return to the court for his former team, the Portland Trailblazers after missing all of last season recovering from his injury.

Lillard recently spoke with Marc J. Spears on Andscape talking about several things including his time in Milwaukee, and how being waived after his injury was one of the darkest moments of his career.

Damian Lillard says being waived by the Bucks after tearing his Achilles was the darkest moment of his career:

“The darkest day was when I was hurt and got waived. It wasn’t a matter of, ‘Am I going to get an opportunity?’ It was just like — it was a possibility and a thought of… pic.twitter.com/2uuuXMheEq
— NBABase (@TheNBABase) October 21, 2026

“The darkest day was when I was hurt and got waived. It wasn’t a matter of, ‘Am I going to get an opportunity?’ It was just like — it was a possibility and a thought of mine. ‘Well, do I just sit the year out and not be on the team and just wait until next summer when I’m healthy, and then go and visit teams and just work out for them and whatever and try to figure it out from there?’ What do you do?”

Another factor what made it so difficult for him was being in Wisconsin away from his family who were back in Portland. When asked about if he considered retiring, he mentioned that his family played an important role and wanted to be around and present with them.

“Not because of the injury,” he said. “But I say it all the time: I don’t put nothing ahead of my kids and my family. You really love your kids and are around them, and you see how important your role is to them having a healthy, quality life as people. Not as far as what you can give them, but what you can instill in them and how you raise them and how you’re able to be present with them. That’s at the center of my heart."

It's been 542 days since Lillard's injury with the Bucks, and he will return to the court for the Trail Blazers on Wednesday night to play in the season opener against the Phoenix Suns.

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