Damian Lillard misses winning, losing, even criticism. Now he’s back with Portland Trail Blazers.

As crazy as it might sound, Portland Trail Blazers guard Damian Lillard missed all the haters, the critiques and even the challenges that came from losing during the first 12 seasons of his career.

The nine-time NBA All-Star’s career has been on hold since he suffered a torn left Achilles tendon on April 27, 2025, during Game 4 of the Milwaukee Bucks’ first-round playoff series against the Indiana Pacers. He was subsequently waived by Milwaukee and returned to Portland, but missed the entire 2025-26 season rehabbing.

Lillard, the Blazers’ all-time leading scorer, is looking forward to the good and the bad as he prepares to return to action against the Phoenix Suns in Portland on Wednesday for his first game in one year, five months and 24 days.

“I’ll say the ups and downs of just … what it takes to be great at this job,” Lillard, 36, recently told Andscape about what he missed during his recovery. “Just everything that comes with it. Winning, losing, trying to figure it out, criticism. All of the stuff that makes it a stressful thing. It’s why we are who we are. It’s why we make it to this level, because we’re able to deal with all of the different layers of being an NBA player, and we thrive under that.

“And as quiet as it’s kept, we all kind of live for that. And I didn’t have that. There was no having to perform, having to prepare for games, having to bounce back from the tough shooting night, having to end the losing streak, having to win big games. I didn’t have that layer to my world for a whole [season].”

Lillard is already arguably the greatest player in Trail Blazers history, having scored a franchise-record 19,376 points for the team from 2012-23. He could become the first Blazer to reach 20,000 points this season, and the Oakland, California, native is also the Blazers’ all-time leader in 3-pointers made, free throws made and free throw percentage. The season opener will be his first regular-season home game as a Blazer since March 17, 2023.

Lillard and new Portland head coach Micah Nori believe the Blazers legend will be “the same” in his return.

“The reason I sat out the entire season was because I wanted to check every box,” Lillard said. “I didn’t want to come limping back or having second thoughts about, ‘Man, can I do this? Can I do that? What should I stay away from?’ I checked every box and I cleared every box, so that was my priority in that process, and I did exactly that.”

Said Nori: “There’s really no loss of his — I’m not going to say explosiveness, but his quickness. But the other thing is, like I tell people: He hurt his lower body, not his upper body. He can still shoot the thing, so his game is not reliant on all that quickness. It’s just more of him getting shots and us finding space for him.

“And the one difference that you’ll see with Dame now is he’ll be off the ball a little bit more than what he was earlier in his career. We can still play him, obviously, in the pick-and-roll. … He doesn’t have to do all that to be able to find him open shots more so in the flow. And you see him competing at the defensive end as well.”

In the 2023 offseason, Lillard asked for a trade from Portland in hopes of joining a championship contender. His preference was to be traded to the Miami Heat, but the Blazers sent him to the Milwaukee Bucks as part of a three-team deal that meant he would play alongside two-time NBA MVP Giannis Antetokounmpo. In 131 games over two seasons with the Bucks, Lillard averaged 24.6 points and 7.0 assists and was their premier scorer in crunch time. Milwaukee also won the 2024 NBA Cup.

The Bucks, however, were upset by the eighth-seeded Miami Heat in five games in the first round of the 2024 playoffs, as Antetokounmpo missed two games with a lower back injury. The Bucks then lost in six games to the Pacers in the first round of the 2025 playoffs, which included Lillard tearing his Achilles and Antetokounmpo missing the entire series with a left calf strain.

When asked about his time with the Bucks, Lillard took a positive outlook rather than the perceived “bad time” there.

“I thought I had two productive years, some All-Stars,” Lillard said. “We were a top-three seed my first year. You almost forget about it because of the way people talk about it. Won the cup one year, and I just think, at the end of the day, we didn’t have a healthy playoff run. For all the adversity that we had as a team, both years at one point or another, we got in the playoffs both times without being in the play-in [tournament].

“We just didn’t have a healthy run, so that kind of puts a black eye on what the experience actually was. My first year, Giannis didn’t play one game in the playoffs, and then the second year I played two games. It’ll be talked about in a more negative light than it actually was.”

Lillard’s time with the Bucks came to an end July 7, 2025, when they opted to pay the remaining $113 million owed to him over five seasons using a stretch provision, rather than paying it out over the remaining two years on his contract. The financial flexibility allowed Milwaukee to sign free agent center Myles Turner to a four-year, $107 million deal last offseason. Lillard returned to Portland shortly after, signing a three-year, $42 million contract.

From the Achilles injury to being waived, that stretch likely marked the toughest time of Lillard’s illustrious career.

For the first time since he began playing organized basketball, he was without a team.

“The darkest day was when I was hurt and got waived,” Lillard said. “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?

“And that was probably the darkest time, because I didn’t really know which way I wanted to go. I would say when I got waived, and it was kind of like that limbo, and I had never not been on the team. I had a stretch of time where I just wasn’t on the team.”

Also making Lillard’s time challenging in Milwaukee was being away from his three young children while going through a divorce. From the moment he arrived in Wisconsin, being away from his children for the first time brought mental strife that made it hard to concentrate on basketball. Being back in Portland has allowed Lillard to see his children regularly.

When asked if he considered retiring after suffering his Achilles injury, Lillard offered a unique answer.

“Not because of the injury,” Lillard 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.

“So, regardless of what I might want or what my career means to me, I always prioritize that. It [retirement] was a thought for a split second for that reason, and that was it.”

Lillard’s lone appearance on an NBA court last season came when he won the 3-point competition during 2026 NBA All-Star Weekend in Los Angeles. Without him, the Blazers surprisingly went 42-40 and made the playoffs while led by All-Star Deni Avdija. They lost in the first round of the playoffs to the San Antonio Spurs in five games.

Lillard actually considered making his season debut in the postseason.

“I definitely thought about it, but it was more if we are able to get through a couple series and I’m able to kind of get comfortable and see that light at the end of the tunnel,” Lillard said. “But I wasn’t sitting there like, ‘Man, I’m targeting the date’ or nothing.”

Today’s Trail Blazers appear to have a deeper and more intriguing roster than last season’s team. Lillard believes they can be “special.”

In his return, Lillard joins standout veterans Jrue Holiday and Scoot Henderson in the backcourt, with center Donovan Clingan anchoring the frontcourt. A major newcomer to the Blazers is two-time NBA All-Star guard Ja Morant, the former Memphis Grizzlies star who has been riddled by injuries and off-court drama in recent seasons. Due to the backcourt logjam, Morant is expected to come off the bench.

Lillard is excited about Morant’s arrival and believes he will prove his naysayers wrong.

“A lot of people have him wrong,” Lillard said. “You see what people say, you see the judgment, and all of that. And we all go through our things, but being around him this much every day, man, he’s a solid dude.

“We share a lot of childhood experiences and laugh about it, but you know, he’s a sharp dude. You can tell he’s a team player, selfless, just naturally the way he plays the game, just the way he comes off.”

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