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Damian Lillard on divorce, move to Milwaukee: 'The hardest transition in my life'

Damian Lillard returned to the place he called home for over a decade, a place many thought he’d never leave. The place he felt he would, one day, hold up the Larry O’Brien Trophy as an NBA champion.

He was cheered and adored, given a standing ovation when introduced to the Rip City faithful, highlighted by a video tribute during the first timeout. All those great moments he authored, not the ugly and confusing ending.

Most people believe an organization-to-player reconciliation will be had sooner or later, and Lillard intimated as much, professing his love for the region and fans he connected with.

“I loved playing in Portland, living in Portland, loved the organization, had a great run,” Lillard told Yahoo Sports during the Bucks’ road trip to Detroit in mid-January. “I just wanted a chance to win a championship. So that’s a lot to let go of.”

That franchise and his time in Portland represented stability and familiarity. Now, in Milwaukee, he’s been experiencing life changes on and off the floor. Most notably, Lillard and his wife of two years, Kay’La Lillard, are going through a divorce. They were college sweethearts at Weber State and share three children. He filed for divorce days after his trade to the Bucks in early October.

Lillard looks back to the time between his trade request and the Trail Blazers finally making a deal. The divorce wasn’t public, but soon would be. So he leaned on a small circle of friends and family. Bible study and candid conversations. He couldn’t train as rigorously as he could in the summer given the circumstances.

“[I did] stuff that wouldn’t make me feel overwhelmed. It can be because we all got feelings,” Lillard said. “We all have stuff we really care about, near and dear to our heart. I’m happy I’m a stable person, I got solid people around me.

“It’s probably been the hardest transition in my life, all things considered.”

Jan 31, 2024; Portland, Oregon, USA; Milwaukee Bucks guard Damian Lillard (0) shows his love for Portland fans during introductions before a game against the Portland Trail Blazers at Moda Center. Mandatory Credit: Troy Wayrynen-USA TODAY Sports
Damian Lillard shows love to Blazers fans upon his first return to Portland after being traded to the Bucks. (Troy Wayrynen-USA TODAY Sports) (USA TODAY Sports via Reuters Connect / Reuters)

The player who won an award from basketball writers for “excellence on the court with cooperation and grace in dealing with the media and fans” now exits the locker room shortly after his duties, ostensibly to get whatever morsel of time he can with his kids who are three time zones away.

Lillard admits this season has been a work in progress on a number of levels. And he’s trying to find the balance.

“You got to keep pushing forward, you know? I think that's the best thing,” Lillard said. “I mean, as people we all know, you got to go home to your own stuff, everybody that can watch our games they go to their personal stuff, and it plays a part in how you do your job and how your every day goes.”

It’s easy to say the game is a sanctuary, a way to free your mind of all that ails. Many have said it and their actions have followed their words. But what if it’s not just a switch, and sometimes, you’re in two places at once?

“As much as I love basketball, and I love my job, I don't care about it more than I care about my kids. Of course you carry it with you,” Lillard said. “People say, ‘When I hoop I ain’t thinking about nothing,' but I’m not 21. I got three kids. I’m tight with my family and I’m going through a divorce.”

He wasn’t offering up the facts as some excuse, as Lillard has a history of being candid. It’s a clear picture, though, a snow globe that’s gotten more jumbled since he arrived in Milwaukee.

As much as I love basketball, and I love my job, I don't care about it more than I care about my kids. Of course you carry it with you.Damian Lillard

When the trade was made, two obvious on-court predictions were tossed out: the Bucks would struggle on defense by sending Jrue Holiday on his way — although they didn’t know he’d be re-routed to Boston — and the world would get a strong helping of Dame-Giannis Antetokounmpo pick-and-rolls.

The defense has indeed struggled, ranking 19th in efficiency. And first-time coach Adrian Griffin didn’t deploy the Dame-Giannis two-man game during his brief tenure. It led to skepticism and the belief that not only will the Bucks not get back to the Finals, but that Lillard would be better off in his original preferred destination, Miami.

“I don’t have to fight against it. Because I’ve been around long enough to know that’s the conversation. It’s never gonna stop,” Lillard said about the Miami talk from the summer. “People will always do that. I take solace in knowing, I’ve seen teams rolling, 50-60 games and the first time they hit adversity or have a collapse, they’ll just roll [over].”

The Bucks are getting their adversity out of the way now, it seems. They destroyed the Celtics on national TV, then got rocked by the Cavaliers in a game without Antetokounmpo. On Jan. 23, the Bucks fired Griffin. A few days later, Doc Rivers was introduced as their new coach.

Even before Griffin was fired, the warning signs were abound. Antetokounmpo called for harder coaching, and Bobby Portis implored for it after an early-season loss.

"When I got traded here, it sounded great. ‘We’re gonna have Dame and Giannis’,” Lillard said, then noting it was never going to be easy. “Ain’t nobody about to roll out here and let you win a championship.”

When Yahoo Sports spoke to Lillard it was days before Griffin was let go, but it was clear everyone was watching how the coach was handling the enormity of the position.

“He didn’t take an easy job. It’s one with pressure and expectations and criticisms. It comes with a lot of weight,” Lillard said. “You gotta be able to handle it.”

The Bucks didn’t believe that to be the case, and now in steps Rivers.

One thing that’s different here for Rivers compared to his previous stops in Los Angeles and Philadelphia: the reliability of his star players in big moments. Antetokounmpo has Finals skins on the wall, and Lillard has put together his own playoff bonafides.

Lillard remembers the 2021-22 season, when he played in just 29 games in Portland due to injury, and the Blazers beat a then-struggling Celtics team in Boston, and the talk was the Celtics were ripe for a breakup.

“They hadn’t figured it out yet, they hadn’t figured out their defense. Then they hit their stride, they made the Finals,” Lillard said. “And I don’t mean that’s what’s gonna happen to us, but it speaks to you can be one place and then …"

Things happened, they clicked. If Rivers can get everyone on board, assign roles and have them followed, the Bucks won’t be far from real contention. Rivers coming in hasn’t signaled an immediate change, but it’s unrealistic to expect it. He and his new staff, they’re learning about this team up close, and it could get rougher before the path gets smoother.

Still, Lillard has remained optimistic about his team’s prospects for the near future.

“My best ball is coming,” Lillard asserts, then interrupts the follow-up. He had thoughts to get off.

“I’m gettin 25 and seven (assists), and people acting like I fell off. Of course it’s not gonna look like Portland. I haven’t shot the ball as well as I’d like to but being productive is being productive. Winning a lot of games and playing a part in those wins …

“I had a stage in my career where they said, ‘Oh, he's doing this. He's scoring 30-plus points. And 50 and 60 and 70 points, but his team ain’t [winning].' I was making the playoffs, I just didn’t win a championship, and that was an issue.”

Lillard was selected as an All-Star Game starter for the first time in his career this season, his eighth overall appearance in 12 years, but knows he has more room to grow to meet his own lofty individual standards. Shooting 42% from the field and 34% from 3 doesn’t mesh with his career numbers, but he’s never played with a high-usage, ceiling-raiser like Antetokounmpo either.

Adjustments have to be made all around.

“I could be doing things better. But we’re second in the East,” Lillard said. “It ain’t about individual performance. How can I contribute to a champion? We’re gonna have a chance.”

For Lillard, it’s one thing to be a franchise player in one place, but that sweat equity has to grow brick by brick, from scratch.

Lillard knew where the discussion was going, to that game against Sacramento on Jan. 14.

Full court … "Yeah”… down two … "Yeah” … no timeout … "Yeah.” Lillard took a pass from Brook Lopez, took four dribbles, stepped to his left and launched a moon ball into the Wisconsin night.

Ball game.

“It shows what I bring to the table,” Lillard said. “Opening night [win vs. Philadelphia], that was a brick. I ain’t even in form right now, I get 39. Down the stretch, zipping the game up. I’ve had plenty of moments like that through the season.

“But I’m not a finished product,” he continued, “we’re not a finished product.”