Damian Lillard’s Return Brings ‘Winning Time’ Back to Trail Blazers

Damian Lillard was driving home on Saturday after signing his new three-year, $42 million contract when he told his kids he was returning to the Portland Trail Blazers.

He had wanted to wait until it was official to tell his son Damian Jr., 7, and twin girls Kalii and Kali, 4. So with the ink freshly dried and all three of them in the car, Lillard turned around at a stoplight by Bridgeport Village to break the news.

One of the girls had several questions for her dad about the development, Lillard recounted.

First: “Wait, so we don’t have to get on the airplane to Milwaukee no more?”

Then: “So you’re gonna be at your house in Portland the whole time?”

And finally: “What!?”

The story of the ecstatic back-and-forth between Lillard and his daughter was one of the many gems the nine-time NBA All-Star shared during his re-introductory press conference on Monday at the Moda Center, sitting alongside Portland general manager Joe Cronin and head coach Chauncey Billups. The 30-minute event was a joyous victory lap for all parties involved for working together to bring back the franchise’s all-time leading scorer.

That story of his daughter’s reaction captured the elation many in Portland are feeling about the unexpected reunion with the sports icon — a buzz that has largely been absent in these parts since Lillard departed for Milwaukee two years ago. It also helped paint a picture of how family and community played such a big role for Lillard in making the decision to return.

While the three men at the podium highlighted the off-court and emotional elements of the reunion, they made it clear this was a basketball decision as much as anything else. Lillard expects himself and the Trail Blazers to play at a high level once he returns from his Achilles tear. Cronin and Billups share that vision.

“Our challenge this year is to keep getting better and to keep prepping to take that next step,” Cronin said. “And once Dame gets back, he’s going to catapult us even further. … It’s winning time now for the Trail Blazers.”

Even while he was away in the Midwest these past two seasons, Lillard kept an eye on his former team. Lillard told tales of returning home from Bucks games with plenty of time to catch Portland games with their later starts on the West Coast. He studied the new-look Blazers as if they were his own team because despite the relocation, they still felt like his team. He analyzed the roster, how he would fit. He noted the progress and liked what he saw. In a league that’s shifting to a new era of parity and younger teams competing for the mantle, Lillard views the Blazers as part of that up-and-coming frontier of new challengers.

“Looking at how the league is transitioning and how it’s changing, it’s not the same old thing no more,” Lillard said. “It’s young teams that guard and that have depth and that compete, that are connected. And this team has all of those things.”

In the final seasons before his departure in 2023, Lillard said he just wanted a roster that gave him a puncher’s chance at an NBA title. He believes he has that here now. He touted that confidence Monday while reminding everybody he’s one of the most polished, motivational interviews in professional sports.

As proof of that last point, take any number of the quotes he dropped Monday about the Achilles tear he suffered in April and his approach to recovery:

Exhibit A: “It’s a mental battle, but I don’t lose those. … If it’s physical, it’s possible [I could lose], but a mental battle, I’m just not going to lose.”

Exhibit B: “After I tore my achilles, and I felt it, and I was sitting on the floor, I grabbed it, and I rolled over, and I sat up, the first thought I had to myself was ‘I’m about to come back from an Achilles.’ That was literally my first thought, on my kids.”

Exhibit C: “When the doctor said, ‘You tore your Achilles,’ I think everybody else had more pity for me than I did. … I didn’t cry. Even when I got by myself I didn’t cry. And it wasn’t like a prideful thing. My mind automatically went to, ‘I gotta fight for something.’”

Lillard emphasized he is looking forward to “pouring into” and mentoring young players like Scoot Henderson and Shaedon Sharpe during his recovery and beyond. Billups gushed about the value of Lillard teaching the young roster, joking that the guard will be the “highest paid assistant coach in league history” next season. With that said, the selection of quotes above don’t read like an athlete who is content to only serve as a glorified mentor or marginal bench piece. It also doesn’t sound like somebody who plans to quietly bask in the comfort of familiarity before transitioning into retirement. This return is another mission for Lillard, not a resignation.

“I expect to return to form,” he said.

In a case of cosmic peculiarity, the unfortunate predicament of Lillard’s Achilles tear is what prompted Milwaukee to waive the star, opening the door for his celebrated return home. Lillard admitted he didn’t expect the reunion to happen this soon. Just two years ago, the relationship between him and Cronin seemed quite sour in the aftermath of a messy split. As Lillard sat next to the GM on Monday, partners once again, he explained the past fissure was caused by misunderstandings and miscommunications during a challenging situation.

“Sometimes when you’re emotional, you handle things from a position of protecting yourself and not knowing what’s going on on the other side,” Lillard said. “And then over time, you calm down and you figure it out. … It wasn’t a long conversation [between me and Cronin] to move past that.”

Once Lillard became available on the free agency market, Cronin said the process of reforging the partnership was smooth and organic. Both sides realized their goals and visions aligned, and they worked fast to lock down a contract. Lillard said he usually puts a lot of thought and time into making decisions, but this was a rare case where the answer came easy. As every speaker said Monday in one form or another: The world makes more sense when Damian Lillard plays for the Portland Trail Blazers.

So when Lillard was at that stoplight Saturday sharing the special news with his kids, the significance of the moment washed over him as well.

“Just knowing that I’m gonna be back home for all parts of my life — with my kids, playing for the Trail Blazers, driving on the same streets that I’ve driven on pretty much my entire adulthood, my whole family being here, my mom, my brother, my sisters, all my friends around, the city of Portland. All of those things count.”