Coach for a season, then the comeback begins for Dame

Joe Cronin (left) and Chauncey Billups (right) welcome back the newest old member of the Trail Blazers

On Monday night at Moda Center, a Rose Room throng filled with media and Trail Blazers employees got a first look at the “highest-paid assistant coach in (NBA) history.”

It was the best quip of the press conference re-introducing Damian Lillard as a Blazer, compliments of his coach, Chauncey Billups.

On Saturday, Lillard signed a three-year deal with Portland after having his contract bought out and being waived by the Milwaukee Bucks. He will sit out the 2025-26 season as he rehabs from surgery to repair a torn Achilles tendon suffered in the playoffs in late April.

“I told him that this year he is going to be the highest-paid assistant coach in league history,” Billups said with a smile. “He will be putting in the work every day.”

When I asked Lillard about it during the 25-minute Q&A session, he said “coaching” is a role he will embrace.

“I want to still have an impact, still be present on the team,” said the veteran point guard, who turned 35 last week. “When you have been around the league for as long as I have, have had as much experience as I have had on the court every day in practice, just being in this league and having a significant role with a lot to share, you have a lot to offer.

“With this being a younger team, there are things I can share without having to be on the floor (playing). That will be my main job this year. I will be like an assistant coach, but my investment in the team will be the same as if I were playing.”

Lillard’s return to Portland after two years in Milwaukee has hearts aflutter among a majority of Blazer fans, who hated to see him go via trade after the 2022-23 season and are thrilled to have him back.

Count Lillard and general manager Joe Cronin among those sharing the feelings.

“It never felt right seeing Dame in a different jersey,” Cronin said.

“It never felt right not being at home,” is the way Lillard put it. “Through it all, I found my way back. I am thankful for and appreciative of the door being open to me to come back, even with me being hurt. It means a lot to me to be playing with this organization again. And to be back in this community, it all just feels right.

“It was a decision that wasn’t hard at all for me to make. It feels like a perfect situation at a perfect time. I would be lying if I said I didn’t expect this to happen at some point, but this soon? I wasn’t expecting it.”

After the Bucks paid Lillard $112 million — his salary for the next two seasons — to go away, many teams showed interest in adding him to their roster.

“We had 26 teams come in with offers, many at the mid-level exception ($14.1 million), which is all they had available,” said Aaron Goodwin, Lillard’s agent. “But most of them wanted him to help them make a run at a title (in 2026-27).”

The Blazers had only the MLE to give, too. But they had more than money to offer someone who played his first 11 seasons with them.

“It was partly a basketball decision,” he said.

Lillard was very familiar with the man calling the shots — Billups was coach his last two seasons in Portland — and the organization. His connection with the fans during his time here was magnetic. To them, he was a deity, the pied piper of a generation. And he loved them back. He made his offseason home here. He purchased an auto dealership in McMinnville. He became an Oregonian.

“It was always organic,” he said. “The city of Portland and the Trail Blazers organization are important to me. It has never been something I have had to go out and try to do. It is just how I feel. I go off of what my true feelings are.”

When he left for Milwaukee, “It was hard to let go of the love I have for Portland, the community the organization, everything,” he said. “The fans know it was genuine coming from me, not from words but by my actions.”

Social media told Lillard his return is a popular decision, he said. And not just because he is such an accomplished player.

NEW: The Dean of Portland Sports is now on BlueSky.

“When it was announced that I was coming back, it wasn’t just about basketball, it was about everything,” he said. “People are excited and happy to have me back as a presence and as a person representing this city and organization. That means more than anything, when people respect who you are and what you bring to the table on top of who you are as a player.”

The Blazers are a young team with potential to get better. Lillard said he watched them play often on TV last season.

“I stayed in touch with what was going on,” he said. “I watched closely. I am always looking and thinking, ‘How would I fit in?’ There are young teams that have depth and can compete and are connected. This team has all that. It is all there, from the depth to the talent on both sides of the ball. I am always looking and thinking, ‘How would I fit in?’ This is like my team. I saw how they cheer for each other on the bench, regardless of who was finishing the game. How they shared the ball. This is one of those teams that is coming along.

“The same old teams are aging out. OKC won it this year. Indiana snuck in and made a run. New York, Houston, San Antonio — some younger teams are moving in. I would put the Blazers in that same category, even though they are not one of the teams that people want to say it about. That’s how I see the team.”

There is no doubt it was partly a personal decision. His family is in Portland — children Damian Jr., 7, and twins Kalii (boy) and Kali (girl), 4, who live with their mother and Damian’s ex-wife, Kay’la Hanson. Mother Gina Johnson, brother Houston Lillard and sister La’Nae Lillard all have continued to live in the Portland area, not far from Damian’s West Linn home.

“It is well-documented that I am a family guy,” he said. “When you have kids, that is even more.”

During a drive to his home on Saturday, after his return was official, Lillard delivered the news to his three children.

“We were stopped at a red light, and I turned around, and my daughter was looking at me, and I told her,” he said. “She was like, ‘So we don’t have to get on the airplane to Milwaukee no more? You’re going to be at your house in Portland the whole time? I was like, ‘Yeah.’ She was like, ‘What?’ Her brothers were excited, too.”

So is Damian.

Lillard says he had personal and professional reasons for choosing to return to Portland

“I am not somebody who gets overly excited,” he said. “I don’t express myself that way. On the outside, you might not be able to see it, but inside, there might be a whole lot going on.

“At that moment, it was a great feeling for me pulling up to a familiar stoplight at Bridgeport. I know my way around here. Knowing I am going to be here for all aspects of my life, with my kids, playing for the Trail Blazers, driving on the same streets I have driven on pretty much my entire adulthood, with my whole family being here and all my friends around the city … all of those things count. There was a lot of emotion in that moment for my kids, but for myself as well.”

It all added up, he said.

“The basketball part, personal part, the family part,” Lillard said. “It felt like the perfect time and the perfect opportunity.”

The contract part, too, was perfect, at least for Lillard. Cronin offered a deal that couldn’t have been more favorable — three years and $42 million with a no-trade clause and a player option after his first season back in action in 2026-27. Including money from Milwaukee, Lillard will make about $64 million for each of the next two seasons, though much of it coming from the Bucks will be stretched over five.

“We knew early on that our goals were very similar,” Cronin said. “Both sides said, ‘Let’s work a deal and get this done.’ It was really that smooth.”

The second part of my question to Lillard was this: Once he returns to action in 2026-27, what will his role be?

“It will be the same,” he said. “One thing I have missed while playing on an older team (in Milwaukee) is … when I have something to pour into, when I am able to be invested in others’ careers more.

“Being around younger players with this team, I will have plenty of opportunity to do that, especially having a young, rising point guard like Scoot (Henderson) who I will be playing with. And Toumani (Camara) and Deni (Avdija) and Shaedon (Sharpe), who I was with his rookie year. Being able to … be a part of their continued progress is something that elevates me as a player, as a teammate and as a leader.”

Lillard will be 36 by the time he steps onto the court in the 2026-27 season. He will be coming off a season without playing a game, after the most serious injury of his career, one that will force him to rehab through the entire 2025-26 campaign.

“There is no reason to rush it,” he said. “It is a tough injury. I know how I will approach the whole rehab process, taking my time. It is a pretty slow process. That is why I am taking next season to check every box and not rush. With age, I am wiser. I am going to take as much time as possible to make sure I am right.”

Lillard said he has spoken with several athletes who have returned to action following a torn Achilles, including Kevin Durant, Rudy Gay and Aaron Rodgers.

“I know it is going to be a long journey,” Lillard said. “I know it is going to be a challenge mentally.”

But he added this: “I think I am going to return to form. That is my true belief. I know what my assignment is to make that happen.”

Added Billups: “He will be back as good as ever, if you know anything about him.”

Billups knows better. The Hall of Fame guard is one of those who went through Achilles surgery, when he was — that’s right, 35 — in 2012. Billups, who was averaging 15 points and four assists in 30 minutes before the injury in 2011-12, played only 41 more games before retiring two seasons later.

The roll call of those who have rebounded well from Achilles injuries is short. Durant, who suffered his injury during the 2019 NBA Finals, is about the only one to get back to pre-injury form.

Dominique Wilkins played seven more seasons, averaging more than 20 points the first four and an All-Star the first two, but never quite got back to where he was. Wesley Matthews (nine more seasons), Gay (seven) and Elton Brand (six) completed long careers but not at the same level. Kobe Bryant had a sharp drop-off, Klay Thompson has not been the same and DeMarcus Cousins played only two more injury-plagued seasons before his NBA career was over.

In 58 games last season with the Bucks, Lillard averaged 24.9 points and 7.1 assists in 36.1 minutes. Dame will work his tail off to get into shape and regain his abilities. If he gets there, at his advanced age, he will be the exception, not the rule.

Lillard has played 968 regular-season and playoff games in his career. He has started in 968 games. I am sure he doesn’t see himself coming off the bench for the Blazers in 2026-27.

Dame has already written his ticket to the Naismith Basketball Hall of Fame. He is fourth in NBA history in career 3-pointers with 2,804. He ranked 37th on the scoring list with 22,598 points, just ahead of Clyde Drexler, Gary Payton and Larry Bird.

But how does Lillard fit 15 months from now when he stops onto the court with a backcourt that includes, presumably, Sharpe, Henderson and Jrue Holiday, among others? No way Lillard plays his career average minutes (36.1), and I don’t see him scoring his average number of points (25.1).

If he can stay healthy, he will provide scoring and leadership, no doubt about that. But how will he fit with Billups’ renewed emphasis at the defensive end, hounding opponents 94 feet up the court? And do his minutes take away from the development of Henderson, who is only 21 and was the No. 3 pick in the 2023 draft?

Asked about Lillard’s role when he returns, Billups demurred, saying he wants to concentrate only on next season.

Really, that is best way to look at it right now. The “Letter O” is back, a big, bold nod to the past. Predictions are for the future, and only time travelers know how that will turn out.

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