“I’m not 21. I got three kids. I’m tight with my family, and I’m going through a divorce.” That’s how Damian Lillard summed up his life. It was a raw, honest moment that reflected just how much his personal life had shifted in 2023 when he filed for divorce from his college sweetheart, Kay’La Hanson. After just two years of marriage, the NBA star cited “irreconcilable differences” for the “irremediable breakdown of their marriage.” Court filings later revealed they had actually been living apart since December 2022. And while their romance may have ended, it seems like Damian and Kay’La still somehow find a way to make headlines, or at least get people talking, whenever big moments come around in each other’s lives.

Their story started way back during their college days at Weber State University, where Dame was chasing NBA dreams and Kay’La was pursuing nursing. They hit it off when Kay’La, as Dame himself shared, would “take care of me. She had the car, an apartment, and bent over backwards for me.” They had three children together—their first son, Damian Jr., in 2018, followed by twins Kalii Laheem and Kali Emma Lee three years later. They even had a fairytale proposal—a wall of roses spelling out “Will You Marry Me?” during All-Star Weekend and a star-studded wedding in 2021. But somewhere along the way, things shifted. And despite having built a life together, they quietly started living apart before the divorce became official in 2023.

And right when Dame’s shocking return to Portland became the talk of the NBA, Kay’La made her own subtle statement, though probably not how fans expected. Amid all the buzz around her ex-husband’s blockbuster move, Kay’La posted a simple Instagram story featuring a gorgeous bouquet. No tags. No names. Just a sweet caption: “I HAVE THE SWEETEST FRIENDS 🙏🧡☺️.” That was it.  Was it just gratitude? Or just a random post with perfect timing? Whatever the case, her little story popped up right as Dame’s move dominated the news cycle, and people couldn’t help but notice.

Despite the end of their marriage, it’s clear Damian Lillard and Kay’La’s lives will likely always be intertwined — if not for each other, then definitely for their three kids. Dame admitted how the separation impacted him deeply, especially during his transition to Milwaukee when he didn’t even have a place of his own initially. “With parenting time, I couldn’t get anything set up… I didn’t get to get things organized in my life,” he shared openly. It’s never easy navigating divorce, especially under a public microscope, but both seem to be finding their footing, especially Damian with his recent Blazers return.

Damian Lillard comes home to Portland

“Officially Official… and all was well in both of my worlds 🫶🏾🙏🏽🦍 #RipCity⌚️” That’s how Damian Lillard announced his big return to Portland on Saturday. After months of wild rumors and “what if” talks, Dame made it official — he’s back where it all started. The nine-time All-Star confirmed that his new contract with the Trail Blazers is “officially signed,” locking in a three-year, $42 million deal that comes with a no-trade clause and a player option for the 2027–28 season. And true to Dame’s style, it wasn’t just about the business. He turned the signing into a family moment, sharing Instagram photos with his kids right by his side as he put pen to paper.

But honestly, who would’ve thought this is how things would turn out? When the Milwaukee Bucks pulled off the blockbuster trade for Lillard in September 2023, it felt like they were shaking up the league. Fast forward two seasons — things went south fast. After a rough stretch in Milwaukee and a devastating Achilles tear during the playoffs, the Bucks waived Lillard this summer to clear cap space for Myles Turner’s $107 million deal. Suddenly, Dame found himself a free agent for the first time in his career. And according to ESPN’s Shams Charania, “Over a dozen teams made minimum and midlevel exception offers to Dame.” The Celtics and Timberwolves even got calls in with him, but Boston couldn’t offer more than $36.34 million, and Dame’s heart? Yeah, it just wasn’t in it.

In the end, it all came full circle. Portland swooped back in with that $42 million offer — $14 million a year, even though Dame’s set to miss the entire 2025-26 season while rehabbing his Achilles. That’s a bold move, especially for a 34-year-old guard coming off such a serious injury. But Portland clearly isn’t just banking on stats. Lillard’s their guy — the franchise icon, the all-time leading scorer, the face of Rip City’s best playoff runs, including that 2019 Western Conference Finals trip. This comeback feels bigger than basketball. And with a young, exciting core around him and Jrue Holiday stepping up in Dame’s absence, the Blazers are hoping they can develop their squad while waiting for their star to make his return.