Damian Lillard spent the first 11 seasons of his career with the Portland Trail Blazers, becoming a franchise legend and one of the NBA’s top 75 players over that time.
asserted
Lillard → spend → time
But despite his 3-point prowess and penchant for hitting incredible shots in the game’s biggest moments, he never found true team success, reaching the conference finals only once.
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he → hit → finals
In the summer of 2023, Lillard requested a trade to a championship contender.
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Lillard → request → contender
What followed was a three-year roller-coaster ride beginning with protracted trade negotiations, a surprising move to the Milwaukee Bucks, an imperfect partnership with superstar teammate Giannis Antetokounmpo and more playoff heartbreak.
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followed → follow → Antetokounmpo
Then, in 2025, in the midst of a second straight first-round postseason exit, Lillard tore an Achilles.
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Lillard → tear → Achilles
A few months later, Milwaukee made the shocking decision to waive Lillard with two years and $113 million left on his contract.
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Milwaukee → make → contract
The ups, downs, loops, twists and turns ultimately led Lillard back to Portland, which signed him back in July 2025.
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which → lead → July
Lillard says the Blazers were the first team to knock on his door after the Bucks let him go.
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him → say → door
“I’m really thankful that as soon as I was waived, it was the first opportunity presented to me,” Lillard told NBC News on the eve of the season of how he ended up back in Portland.
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he → ’m → Portland
“They know that I can be counted on.
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I → know → ?
They knew that I wasn’t gonna accept the injury and just be done.
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I → know → injury
They knew how I was gonna respond to that.
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I → know → that
Lillard landed in Milwaukee on a team loaded with championship expectations.
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Lillard → land → expectations
During his first season with the Bucks, the franchise changed head coaches.
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franchise → change → coaches
Meanwhile, his chemistry with Antetokounmpo — who has since been traded himself — was constantly called into question.
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who → trade → question
Even as Lillard continued to average more than 24 points per game, the team couldn’t find consistent success.
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team → continue → success
Injuries marred both postseason runs as Lillard and Antetokounmpo appeared in only four playoff games together — and won only one of them.
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Lillard → mar → them
At the same time, Lillard dealt with personal struggles, once describing his time in Milwaukee as “lonely,” as his family remained in Portland.
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family → deal → Portland
But he believes the three-year detour from the team that drafted him has ultimately proved to be beneficial for what most assume is the final act of his career.
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most → believe → career
“I don’t regret any part of the journey.
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I → regret → journey
I feel like it was all necessary,” Lillard said.
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Lillard → feel → ?
“The team that I’m on now couldn’t be formed if I had never left.
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I → ’m → that
We would still be trying to find ways to get players, as opposed to having to rebuild, developing guys and having the assets to do that.
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We → try → that
That required me to go.”
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That → require → me
He added: “I always look at things and I tell myself, whether it’s good or whether it’s bad, I’m always seeking out those opportunities to let my true character show and just keep rising.
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character → add → opportunities
Whether something didn’t work out or whether I was criticized for something or whether people think I’m done, I’m always looking for the opportunity to show how real and how thorough I really am at heart.
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I → work → heart
Lillard signed with the Blazers in the summer of 2025, but he missed all of last season as he recovered from his Achilles tear.
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he → sign → tear
He has since rejoined a team that made the playoffs without him last season.
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that → rejoin → him
In the summer, Portland added former All-Star point guard Ja Morant, leading to another round of questions about how Lillard will mesh with a high-profile player.
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Lillard → add → player
The Blazers enter their Tuesday tipoff with the Los Angeles Lakers (10 p.m. ET on NBC and Peacock) with a 2-0 record.
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Blazers → enter → record
Lillard is averaging only 28.5 minutes a night through the team’s first two games.
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Lillard → average → games
He scored 25 points in Portland’s season opener and followed that up with 19 more in a win over Sacramento.
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He → score → Sacramento
The Blazers have an eclectic roster that is being deftly managed by first-year head coach Micah Nori through two games.
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that → have → games
In addition to Lillard and Morant, Portland also has two-time champion Jrue Holiday (who was actually part of the Lillard trade in 2023) and former No. 3 overall pick Scoot Henderson in the backcourt.
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who → have → backcourt
Rounding out the roster are up-and-coming big man Donovan Clingan, wing defender Toumani Camara and forward Deni Avdija, who was an All-Star last season.
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who → round → roster
To Lillard’s earlier point, his departure helped put the current roster together.
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departure → put → roster
The trade with Milwaukee led to the arrivals of Camara and Avdija.
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trade → lead → Camara
The subsequent rebuild landed the draft pick to take Clingan.
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rebuild → land → Clingan
And the Bucks’ decision to waive Lillard gave him the financial freedom to sign a team-friendly deal with the Blazers.
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decision → waive → Blazers
The result is a deep team that doesn’t force Lillard to carry the burden of winning on his shoulders.
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that → force → shoulders
…and 25 more, not listed.
The Aporia
