Damian Lillard Is Never Leaving Portland for a Superteam

Damian Lillard is fully committed to Portland, telling us he has no desire to leave the city he loves to chase a championship somewhere else.

Damian Lillard Aug 2019 Wide 1 Complex Original
Complex Original

Damian Lillard Aug 2019 Wide 1 Complex Original

Damian Lillard Aug 2019 Wide 1 Complex Original

What does loyalty actually mean?

In a sport where max deals no longer guarantee full commitments from the best players, whose pledges of devotion to a city and its fans often ring hollow, it’s a question perfectly suited to perhaps the NBA’s most loyal superstar.

It’s a hot summer afternoon in late July on the leafy, sleepy campus of tiny Multnomah University, a private non-denominational Christian school east of downtown Portland. Inside the appropriately named Lytle Gymnasium, sitting on the kind of weathered wood bleachers you only find at the smallest and oldest facilities, is Damian Lillard. Wearing a black T-shirt with his personal logo slapped over the left breast, black shorts, and a pair of his new signature Adidas sneakers, which are months away from hitting shelves, the 29-year-old is every bit the calm, cool, and collected guy who barely showed any emotion after hitting one of the most absurd series-clinching shots in NBA history this past April (except for, you know, waving the Oklahoma City Thunder bye-bye). Rarely do you catch Logo Lillard smiling on the court or in front of a camera or when he’s being peppered with questions about the changing landscape of the NBA and where he fits into all of it. In the right setting, around the right people, he’ll flash it. Lillard will even bust the balls of one of his boys, subtly flipping off his pal sitting off to the side when the friend glances up from his phone for a few seconds. But when you’re there to ask the All-NBA guard straight-up questions, he’s going to look you sternly in the eye and give you straight-up answers.  

“I'll just tell you the truth,” he says.

About, for example, how he can’t imagine doing what so many fellow stars are doing these days: abandoning communities and organizations that have bent over backwards to build around them only to watch their star ask out to chase a championship elsewhere. In the wake of guys like Anthony Davis, Paul George, and Russell Westbrook requesting and receiving trades this off-season, Lillard’s proclamation that he’s serious about wanting to spend his entire career with the Trail Blazers, preferring to be a shepherd in the Pacific Northwest instead of a sheep in a city he doesn’t want to relocate to, isn’t revelatory. But after surveying the new NBA, especially the revamped Western Conference, devotees of the old school will find it refreshing that he’s doubling down on his commitment, on his loyalty—with one important caveat. 

“It’s not so much about an organization,” says Lillard. “It’s to the city.”

As happy as he is to be a Blazer, and as much as he desires to one day be considered the franchise’s greatest player ever, what Lillard loves, and where his true loyalty lies, is to the city of Portland. Because basketball is a business, he knows things can change and the Blazers may eventually no longer need his services. But how he goes about his business today, tomorrow, and for the foreseeable future will almost assuredly be different than any other top 10 player in the game. The East Oakland native is home in Portland, with zero desire to pack up and play elsewhere. 

Damian Lillard Aug 2019 Wide 2 Complex Original

Like every basketball fan this summer, Lillard paid attention to all the moves during free agency. He actually made news himself during the start of it when he inked a four-year, $196 million supermax extension that could keep him with the Blazers through the 2024-25 season. The organization showed its appreciation and commitment with a breathtaking amount of money—after it kicks in for the 2021-22 season, he will be the NBA’s first $50 million-a-season player. But the extension barely registered as a blip on the basketball world’s radar while it held its breath waiting for Kawhi Leonard to sign somewhere, anywhere. And that ushered in the madness.

Leonard said yes to the Clippers, provided they could get George from the Thunder. Once George was shipped out of OKC, Westbrook decided he wanted out, too, and wound up with the Rockets. After months of speculation and rumors, the Davis trade to the Lakers finally became official on July 6. Three superstars made three power moves to join contenders in the Western Conference, showcasing a level of clout the league had never really seen on such a scale. Lillard is happy those guys ended up where they wanted to be—in bigger markets, playing for legit title contenders. You’ll just never see him pull something like that.  

“I think people are taking control because there’s no greater time to do it than now,” says Lillard. “And I don’t have a problem with that, but the way I see stuff is, like, I don’t prefer to go that route. Just like they’re choosing to do this stuff for their career, I’m choosing to do what I want for mine, too.”

He’s not making the goal of winning an NBA title any easier on himself with that attitude. And he knows it. Seriously contending for a championship in Portland is always going to be way more difficult than in a place like Los Angeles for obvious reasons. Its notoriously gloomy weather, its far-flung location, and other quality-of-life factors have made it a struggle for the Blazers to attract and retain top talent during the franchise’s 50 years of operation. Lillard’s seen plenty of guys proclaim their love for Portland and then leave. He wishes all his teammates vibed with the city the way he does. Backcourt mate C.J. McCollum, who also signed an extension with the Blazers this summer and is putting down roots around Portland, has shown a similar commitment to Lillard's. Teammates for the past five seasons, the tandem experienced its first deep run through the playoffs last season. It made Lillard double down on his desire to win in the Rose City. Fuck joining a superteam somewhere else—Portland’s where it’s at, where he wants to get it done. 

“If I go play with three other stars, I don’t think that many people would doubt that I could win it. We would win it, but what is the challenge or the fun in that?”

“To leave, what did I invest all this time for just to leave, you know?” he says. “If I go play with three other stars, I don’t think that many people would doubt that I could win it. We would win it, but what is the challenge or the fun in that?”

This love and respect for the city of Portland started over a decade ago, when Lillard was looking forward to games against Portland State during his days balling at Weber State in the Big Sky Conference. Portland was the only major city they would play in, and it was a big deal every time they came through. Then the Blazers selected him sixth overall in the 2012 NBA Draft and his best friend just happened to be attending Lewis and Clark University in the city. “It automatically felt right,” says Lillard. His mother and sister quickly moved to Portland. Soon enough, Lillard stopped returning to East Oakland during the off-season and Portland was officially home.

He’s found the spots and the people that make him the best version of himself in a city that hasn’t always been the most popular for Black athletes to make their year-round residence. He’ll say it often, but Portland “just works” for him. It’s safe, it’s comforting, and there aren’t anywhere near the amount of distractions you’d find in a bigger city. As a bonus, the North American headquarters of Adidas, his sneaker and apparel sponsor since he entered the league, is located in Portland, so he can jet over to collab just about anytime. “They have meetings and questions, and they’ll be like, ‘Dame, what do you think about this? We’re having a meeting,’” he says. “And I’ll be like, ‘I’ll be there in 20 minutes.’” 

Portland is where he is thriving, where his family has come to join him, and where he has become a top 10 NBA player, earning way more money with the Blazers than he ever could elsewhere thanks to the intricacies of the league’s collective bargaining agreement. Why leave? Seven seasons after his arrival, Lillard’s unquestionably one of the best guards in the game and possesses the kind of influence few players ever find within an organization. In his fourth season, the Blazers gave him more of a leadership role and he rewarded them with a run to the Western Conference semifinals. By his fifth season, the front office wanted him weighing in on roster moves. He’d attained a unique level of power in the modern NBA. But with great power comes great responsibility.

“Once they started bringing me in and asking for my input and all of this stuff, I realized how much my opinion counted and my involvement counted,” he says. “I realized not that people’s careers were in my hand, but how much of an impact I could have on other guys’ careers.” 

He’s keenly aware of the domino effect a change in his desire to stick around Portland would have on so many people—family, friends, teammates, the organization, and the city itself. He’s legit friends with just about every teammate and does all he can to earn their trust and loyalty, hoping to sell them on the city he capes for. He wants them to embrace Portland the way he has and grow with him and grow with the organization. But in an NBA where young, talented players are just as concerned with their brand and being in a cool city where they can maximize off-court opportunities, that kind of loyalty is increasingly hard to find.  

Damian Lillard Wide 4 Horizontal Complex Original 2019

So, too, apparently are reverence and respect when you wade into the subculture that is NBA rappers. As many know, Lillard has bars—Complex Sports asked in 2017 if he was the best rapper-athlete—and he has no doubt that he is basketball’s GOAT. “Bro, I’m the best NBA rapper of all time,” he says.

And because the NBA is really a reality show masquerading as a sports league, perhaps more newsworthy—and certainly more entertaining—than his extension this summer was Lillard’s diss track directed at Marvin Bagley Jr. On the night of the NBA Draft, Dame D.O.L.L.A. (as he’s known artistically) released “MARVINNNNNN???” and eviscerated the Kings forward, hijacking NBA Twitter in the middle of the one of the league’s marquee events.  

Bagley, like a number of NBA players, dabbles as a rapper. According to Lillard, Bagley had previously hit him up about his about music—“big bro stuff,” as Lillard puts it—and inquired when he’d release another album. Even though it caught Lillard by surprise when a tweet from ESPN’s First Take said Bagley wanted to challenge him to a battle, Lillard was prepared. He had heard an older track from Bagley that mentioned his name that had, “like, eight plays or something.” Lillard just happened to be in an Arizona Airbnb with a studio when Bagley issued the challenge, and he told his engineer to release the track.

“I always told myself, even if one of these dudes says my name and some stuff like that, I’m not about to get into it with them,” says Lillard. “I literally decided that this is the one time that I’m going to do it.”

The two-minute-and-six-second track ended the battle before it ever really had a chance to heat up. Lillard kicks it off basically laughing at Bagley’s “amateur bars” and then puts the Duke product in his place.  

Was about to pass, because you’re still in a Pamper, bruh
And I never seen Floyd spar with amateurs 
You a clown, so go and enjoy the circus
Knee-deep in the game, and you barely scratching the surface
How a King come to battle, knowing the kingdom worthless

“I'm not in competition with no player that’s rapping in the NBA,” says Lillard. “I'm literally as an artist trying to move myself into what the actual artists are doing, but he was starting coming off like he was competing with me, like, ‘I’m the best rapper in the NBA.’”

Lillard’s fed up with fellow ballers saying they’re going to drop an album and nothing ever comes out. Meanwhile, he just released his third, BIG D.O.L.L.A. With features from Lil Wayne, Jeremih, and others, the album’s theme is partly success. Lillard is pretty humble for an NBA superstar, but he’s unfathomably rich and wildly successful, and will not apologize for rapping about it and reveling in it.

“I’m not going to downplay it, because I don’t want you to think I've changed,” he says. “I know that I’m the same and I’m going to do the same stuff and I think the same with everything, but I live in a mansion. It’s kind of a flex, but not, like, a ‘wow’ flex.”

“I wanna be the one, the star that wants to be here...and then be a part of the rise from ‘we haven’t won since ’77, and now we won, and Dame’s everything to our city.’”

As loyal as Lillard has been, of course there will come a time when the Blazers’ loyalty to him will be tested. There are so few examples of a star spending his entire career with one team that Lillard knows retiring a Blazer is far from a guarantee. Kobe Bryant and Dirk Nowitzki are notable exceptions, and while he won’t compare himself to those legends, Lillard knows that things could change with the Blazers on the other side of his prime. “When you aren’t the same player, and you aren’t as important to their organization, that’s when they are going to hit you the hardest,” he says. That’s why Lillard wants to be very clear about where his loyalties really lie. He loves the Blazers—don’t get him wrong—but he loves Portland.

“They could trade me next week, you know what I’m saying?” he says. “So I couldn’t say my loyalty is to an organization. It’s to the things around the organization.”

Lillard has carried the values of an upbringing that taught him never to turn his back on his family or his community, and where sharing was the rule, not the exception, into his everyday life in Portland. He moves around town freely, and the love he’s received, he’s returned. Like when he recently purchased five pairs of sneakers for a few kids he ran into at a Portland Adidas store. That random act of kindness went viral, but on a quieter scale, how many NBA superstars would walk around the Portland International Beerfest in the middle of summer without it being a big deal? That’s what happened at the end of June, when Lillard dropped by the event in yet another example of him roaming around town, sampling its activities and unique culture whenever he has downtime. 

“He’s always in the city. Certain guys, they barely go where there’s a lot of people,” says a friend of Lillard. “He’s just a regular dude. He just happens to play basketball and be that good.”

The Blazers plan on Lillard being their guy through the 2023-24 season (he has a player option for 2024-25). They rewarded him with that massive extension after his best overall season this past year, when he averaged 25.8 points, 6.9 assists (a career high), and 4.6 boards per game, earning second-team All-NBA honors. He helped carry the Blazers to the franchise’s first Western Conference Finals appearance in 19 years, and they’ll be considered a legit threat in the wide-open West next season.

“Since the day we drafted Damian, he has exemplified every quality an organization could hope for in a franchise player,” Blazers president of basketball operations Neil Olshey said in a release announcing the extension. “His perpetual leadership, willingness to embrace responsibility for outcome on the floor, and ability to set a cultural standard illustrates what it means to be a Portland Trail Blazer and makes us ecstatic he has chosen to extend his contract at the first opportunity.”

The stars that have come and gone in Portland are plentiful. Bill Walton eventually asked for a trade after leading the Blazers to their only title. Clyde Drexler was shipped to Houston after a 10-year run that included two Finals appearances. And most recently, LaMarcus Aldridge took his talents to San Antonio after nine seasons and four All-Star appearances. Lillard knows the Blazers’ history and is adamant that he wants to be different.   

“I wanna be the one, the star that wants to be here,” says Lillard. “I wanna be the one that embodies all of those things and then be a part of the rise from ‘we haven’t won since '77, and now we won, and Dame’s everything to our city.’”

Lillard comes off as a cool customer—leisurely but truthfully answering whatever question is thrown at him. A shrug, a sigh, or a subtle eye roll is about as animated as he’ll get this afternoon. There’s supreme confidence in every answer. It could be confused for cockiness, but it shouldn’t. Nor should any of his declarative statements—like the line about wanting to mean everything to Portland—come off as nauseatingly narcissistic. We all want to mean something to somebody, and certain people have the platform to mean more to a group, to a community, to a city. Lillard fits that bill, for sure, but he also possesses way more humility than most guys with a resume like his. He refuses to call himself a superstar, even though he most definitely is.

“I know what I am as a basketball player and as a person,” says Lillard. “I don’t see myself as above, elevated, or, like, more important than other people. I view myself with people; I don’t view myself as a superstar.”

Portland or bust. Either Damian Lillard gets it done where he wants, and on his terms, or he doesn’t. And he’s cool with that, even if haters will clown him for it. You don’t need to get on his level, but you should appreciate his loyalty to a city, to a community, to an ethos.

“I just am who I am, and that fits here.”

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