Amid chaotic offseason, Damian Lillard's meeting with LeBron James as decision loomed sealed recommitment to Trail Blazers

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WEST LINN, Ore. — It’s about 9:30 p.m. on a Thursday, and Damian Lillard is in his living room, watching on TV as the Memphis Grizzlies play the Golden State Warriors.

Dame Jr., his 2-year-old son who is full of energy, suddenly enters the room to play with his toys on the coffee table in front of the television.

“Son, it’s time for bed,” Lillard says.

His son replies in a soft voice, “Aw, I need a little more time.”

Dad laughs and asks, “How much time do you need, Son?”

“Five minutes.”

Everyone chuckles.

“OK, I’m putting the timer on my phone,” Lillard tells him, and Junior nods.

Five minutes later, Lillard’s alarm goes off. “Son, OK, it’s time to go to bed.”

The disappointment is all over Junior’s face. He doesn’t cry, though. He sadly allows his dad to walk him to bed, learning a lesson: Five minutes isn’t long at all.

Dame Jr.’s lesson is an apt metaphor for his dad’s basketball career. Time is short, and you have to take advantage of every minute. Lillard has always been aware of this. That’s why Dame Time was almost on the verge of running out in Rip City.

Meeting with LeBron James in L.A.

Damian Lillard was in Los Angeles in early July to shoot a music video for his new single, “We The Ones,” off his fourth studio album project titled “Different On Levels The Lord Allowed.”

His musical enterprise was a welcome outlet from the uncertainty he faced with his full-time occupation.

The Portland Trail Blazers star was nearly a month removed from a disheartening first-round playoff exit administered by a shorthanded Denver Nuggets unit that was without prolific starters Jamal Murray (ACL) and Will Barton (hamstring). It was the most painful, discouraging defeat the six-time All-Star had swallowed in his NBA career.

It stung so much because Lillard’s ultimate objective is to bring a championship to the city of Portland. And for the first time in his career, he questioned whether the organization shared his objective and his urgency.

After the Game 6 loss, a dejected Lillard shot straight: “Where we are isn’t good enough to win the championship if it’s not good enough for us to get out of a first-round series with two of their best three or four players not on the floor.”

This was Lillard’s most public, direct critique of the franchise, and for someone who has always worn the anti-super-team badge of honor, his comments caught the attention of not just those associated with the Trail Blazers, but the entire NBA community.

The day before Lillard was to shoot his music video, he made a surprise appearance at a WNBA game, featuring the Los Angeles Sparks and Las Vegas Aces. Upon arriving, Los Angeles Lakers star LeBron James was already sitting courtside. On the way to his seat, James stood up to acknowledge his “Space Jam: A New Legacy” cast member. The two shook hands and exchanged a laugh.

Later that evening, James sent Lillard an invitation to his mansion in Brentwood.

“He was like, ‘Pull up. Let’s have lunch to talk shop,’ ” Lillard told Yahoo Sports. “So I pulled up.”

A side profile shot of Damian Lillard looking on during a game.
Portland Trail Blazers star Damian Lillard was at a turning point in his basketball career this offseason before a meeting in Los Angeles with Lakers stars LeBron James and Anthony Davis. (AP Photo/Matt Slocum)

Lillard’s future in Portland was in the balance at this point. He bled Rip City, but he was weighing all of his options.

Through the years, James hasn’t been shy — publicly and privately — in relaying how thrilling it would be to share the same jersey as the Oakland native.

The 6-foot-3 guard caught an Uber from his hotel to James’ house. After security opened the gate for the vehicle to enter the property, Lillard was met at the door by a house staffer who escorted him through the living room and into the elevator. The destination was the rooftop.

When the elevator reached the top floor, James and fellow Lakers star Anthony Davis were sitting on one side of a table waiting for Lillard to join them on the other side. Before they fully dove into lunch of an Italian salad followed by pasta and a fine bottle of rosé wine, James kicked off the conversation, detailing his experience living in Los Angeles.

Lillard did not categorize the meeting as a platform for a recruiting presentation, but rather an information-gathering forum among respected peers.

“’Bron asked what I was thinking with my situation, and I told him what I’m telling you: that I just want to be in a position to win it all,” Lillard told Yahoo Sports. “He painted the picture to me that if I were to leave, the situation could look like this. He didn’t tell me to come to L.A., and he didn’t say anything to me that I didn’t already know other than what it could look like. I told him, ‘I know if I were to play with y’all, I know it would work out because of my skill set,’ and who I am and who they are.”

They all addressed their respective first-round losses, and what each team needed to improve its roster. Davis explained his transition to Southern California.

Lillard expressed his hesitancy to join any iteration of a super-team.

“I was just saying, I don’t know if this is the route I wanted to go,” Lillard told Yahoo Sports. “And that was pretty much how the conversation went.”

The meeting lasted for an hour and a half.

Lillard promised to keep them posted on what he decided to do, but the Lakers were already privately evaluating their options on potentially landing Lillard, sources said.

While Lillard waited for his Uber, James showed him the rest of the house and around the backyard. The Uber showed up after 20 or so minutes and whisked Lillard away. This much was clear: There was no way Trail Blazers president of basketball operations Neil Olshey would ever trade Lillard to the Lakers.

Though joining the Lakers wasn’t at the top of his list, that Lillard took the meeting with James showed how much he respected the four-time NBA champion and how much he was receptive to the idea of trying something new.

“The whole time I knew I was a Trail Blazer, but obviously coming off that playoff loss, I was like, ‘We got to do something to show we’re actually trying to win it,’ ” Lillard told Yahoo Sports of his conversation with management. “There are so many teams in the league where some want to tank; some teams just want to be a playoff team and see if they can make things interesting; and then there are a few teams with the mindset of winning a championship.

“So for me, I was in that position where I was wondering if we’re actually trying to win a championship. I want to be a part of something where winning a title is everybody’s mission. I was asking my team, ‘Is that what we’re really trying to do? What are we doing to show that’s what we really want?’ Those were my questions, and I presented them that way. Like, ‘What are we doing? How are we honestly saying we want to win it all? What steps are we taking?’ I just had a decision to make.”

The arrival of Chauncey Billups

Becoming an NBA head coach was Chauncey Billups’ dream. His basketball acumen, his playing resume, his communication skills and his relationships are essential traits of a promising up-and-coming coach.

Having the opportunity to coach one of the greatest point guards of all time also was a tantalizing proposition. Yet, Billups was hesitant.

With only 30 NBA head-coaching jobs, occupying any one of them is an accomplishment. But Billups’ fear was being placed in a similar situation to that of Houston Rockets head coach Stephen Silas whose best player — James Harden — forced his way out shortly after Silas took the job.

This was beyond Billups’ control.

For two months, Lillard weighed his options as speculation swirled. He went over several scenarios with his agency at Goodwin Sports. Billups never tried to influence Lillard’s decision, but he wanted to be a sounding board for him. Lillard still coveted a roster capable of making a legitimate championship run, but he knew the Trail Blazers didn’t have the cap flexibility for a robust move outside of a trade.

In feverishly pondering the route to take, something kept pulling him back to Portland.

“When I was like, ‘Man, what if I’m not back in Portland?’ When I actually had that thought, it just runs so deep with me to win here,” Lillard told Yahoo Sports. “I want to win here. I’ve attached myself to the history of this organization and this city. Just in thinking about how long it’s been since they’ve won, I want to be a part of that coming to an end. I want people to say, ‘When Dame came through here, he rode all the way out for us through the good and the bad. He was ready to sink with the ship.’

“When I think about how I want the people around me to be like, I try to be that as a Trail Blazer. It’s not always going to be peaches and cream. It’s not always going to look good. You're not going to get the praise. It’s a small market. You’re going to miss out on certain things. S***, you may never win. But if I did decide to go do something else, there’s also no guarantee that I’m going to win it by moving on.

“So, my best bet is to stick to my guns and do what I care about in my heart. Now, if I was to move on and I get there and it doesn’t work out and then they decide to blow it up, and now I’m a part of a deal going somewhere else. You look at some of the dudes around the league that was at the top of their game and they made one move and now they’re on this team, next year on another team and now they’re somewhere completely different. As much as I want to win, I want to do it my way.”

Olshey believed in Billups, hoping his arrival would take the team to greater heights without major roster changes. That has yet to be seen as the Trail Blazers have struggled to a 3-4 start with Lillard shooting 34.9% from the field and 23.1% from deep. His 18.6 ppg is the lowest mark of his career.

However, the team struck gold with the biggest offseason acquisition connecting so fast with the franchise player.

Chauncey Billups and Damian Lillard talk on the sideline during a game.
Portland Trail Blazers coach Chauncey Billups and star guard Damian Lillard have connected early in the first-year head coach's tenure. (Steph Chambers/Getty Images)

“When I started to interact more and more with Chauncey, I haven’t met a lot of people when I talk to them where our lenses are the same,” Lillard told Yahoo Sports. “The way we see stuff, it was just lining up and I could tell he wasn’t trying to line his up with mine. It was organic, and my history of knowing him, he’s always been like that. That, combined with his success as a player and him playing my position, I decided to stick to what I’ve always been and what I’ve always said, and I’m willing to live with the results of that.”

Lillard recently redeclared his commitment to the team, dismissing the vultures circulating around his discontentment.

“Obviously, things were unstable for a second,” Billups told Yahoo Sports. “I didn’t know what would happen, but it was a dream for me to get my first job coaching the best point guard in basketball. I felt like he could help me as a coach, and I could help him as a player. To me, it was the perfect marriage. There were obviously things a lot bigger than me coming in that Dame had to think about, but for him to recommit to the fan base, the city and the team, that’s just reassuring for all of us.

“But we all owe it to Dame to try to do the best we can do. I said it before, there are two teams in the NBA: teams that are looking for a superstar; and teams that have one. We have one of the best, and we need to win for him.”

The 10-year guard didn’t necessarily get the roster shakeup he called for, but he insists that he’s in a better place with the organization after a few meetings with management and team ownership.

“The conversations I’ve had with Neil, he didn’t promise me we’re about to get LeBron,” Lillard told Yahoo Sports. “They didn’t tell me we’re about to go get a superstar player because I don’t think you need all superstar players to win. We’ve got C.J. [McCollum]. He’s an All-Star-level player. We’ve got [Jusuf] Nurkic. He’s one of the best centers in the league. It’s the way you piece the team together.

“If you look at Phoenix, they don’t have a bunch of stars. They got people who are really good at what they do and understand their roles. Chris Paul and Devin Booker are All-Stars, but Deandre Ayton is a quality center, Jae Crowder is an experienced, quality stretch-four man that’s tough, Cam Johnson is nice and Mikal Bridges is my favorite small forward in the league. You just look at how that team is put together and they’re in the Finals coming out of the West. That’s what my vision is.

“I don’t see us just landing star players. I’m Dame Lillard, and C.J. is C.J. McCollum. We have the core pieces to do the same thing that Phoenix did. It’s just how you fill that in. We just got on the same page. Me, Chauncey and Neil. We all spoke and we got on the same page as far as what my thoughts were and how I feel like we can win it. That was good enough for me. I had trust in that. But, we’ll see. They can’t guarantee me anything and I can’t guarantee anything to them, but we got on the same page.”

Family dynamic

Lillard married his longtime girlfriend, Kay’La, in the offseason. They share three beautiful children together. He has a large family with the family cookout in Portland drawing up to 60 members. And that amount significantly jumps if the cookout is in Oakland.

Lillard has around 30 family members who have moved to the Portland area. His immediate family attends every game, and they wait for him in the family-and-friends section of the Moda Center to leave as one for a postgame dinner. Dame Jr. roams the hallways of the Moda Center like he’s at home.

If Lillard decided to leave, he understood it could also disrupt his family. Family members were aware Lillard was mulling a decision that could change a reliable dynamic that has been in place for almost 10 years, yet wanted only to support him.

“My family was encouraging me to not make a decision based on them,” Lillard told Yahoo Sports. “They were like, ‘We’re going to be fine.’ But I know they said that to be unselfish. So when I was thinking about potentially leaving, I was thinking if it’s really worth it to chase what all these other people are telling me I have to have, or is it more important to just do what means something to me. If there’s anybody in this league that moves to the beat of their own drum, it’s me.

“I think the media is so strong now that a lot of top players have become influenced by the media. And for me, I think some media people have an issue with me or they view my stance as coming off a certain way. I don’t tune out what they say, but I just do what I want to do. And I think people look at it like, ‘Ah, he’s just taking the money. He doesn’t want to win.’ The media is so accustomed to rocking the boat and making people move how they want to move, and that’s not going to happen with me.

“I’m sure it would be great to play with LeBron and AD and play in a big market, but as attractive as it sounded and as fun as that might be, I don’t feel in my heart that that’s who I am or where I belong. And one thing I want to emphasize is that this decision wasn’t made out of comfort. I’m not afraid to be out of my comfort zone because I’m going to live here when I’m done playing regardless. I made my decision based on what I actually want to do.”

Known as Big Hou, Lillard’s father, Houston Lillard Sr., played an instrumental role in his son’s decision to remain in Portland without saying a word.

Big Hou is known in Oakland as someone not to be messed with. He doesn’t talk much and seldom smiles, which makes him an intimidating presence to some. If you’re around him enough, his vibe will let you know how he feels. When he does talk, he imparts wisdom.

“I can tell my dad wasn’t really into me leaving,” Lillard told Yahoo Sports. “My dad felt where I was coming from in thinking about leaving. But in our conversations, I could tell by his reactions and energy that he was never a fan of going somewhere else. Any time I’ve ever brought something up to my dad, if he supported it, he would be like, ‘To hell with them. Go.’ I guarantee that would be his exact words: ‘To hell with their ass.’ And if he was in support of me doing something different, that would have been his response.

“But I knew he really preferred me to stay put and see it through how I’ve always felt from the beginning because he never even made a comment about me going somewhere else. And then when I told him I was going to stay in Portland and told him how much I liked Chauncey and the staff, he was happy to hear it. That made me more comfortable with my decision.”

Giannis’ moment

As the final buzzer sounded, Giannis Antetokounmpo exuberantly began hugging multiple family members. Once he embraced those loved ones who were permitted to be on the court, he took his new Milwaukee Bucks championship hat, put it on and briefly collapsed to the floor near the bench, overwhelmed with emotions.

Antetokounmpo then took a seat along the baseline and soaked in the scenery while tearing up. He put a towel over his face for a short time to cover his raw state. When he removed the towel, he rose from his seat and screamed, “Yeah!!!”

It’s an iconic scene that will be replayed on NBA highlight films for decades.

It has become increasingly rare for a star player to win a championship on the team they were drafted by. James, Stephen Curry, Kawhi Leonard and now Antetokounmpo share the feat. That’s the company Lillard seeks to join.

Lillard recalls paying attention to The Greek Freak’s every move when the confetti began pouring from the rafters. It helped reconfirm his initial desire.

“Usually when people win championships and start getting all emotional, I’m always wondering if they’re really moved like that,” Lillard told Yahoo Sports. “Is that real emotions? Does he really feel like that? Because I’ve been in big moments and people would expect me to be emotional and I’m not. So I question the authenticity of how emotional they are in some situations.

“But when I watched Giannis, he was really looking around like, ‘Damn, what if I really left Milwaukee? This was worth it.’ So for me, I put myself in his shoes. Sometimes it seems like this is impossible and it’s never going to happen, and I’m sure he was there before, too.

“If I was to get that championship for Portland, I would cry, bruh. Bruh, on the spot. I would really cry, bro. I want to win a championship here. And because of how strongly I feel about that, I don’t know how rewarding it would feel for me at this point if I won somewhere else. Winning it here would be a lifetime achievement for me.”

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