Wale and Damian Lillard were already friends. It was June 9, 2013, and the occasion was a "Block Party" set up in Oracle Arena’s parking lot for Bay Area radio station 106 KMEL's Summer Jam. The D.C. rapper and freshly crowned NBA Rookie of the Year, back in his hometown, chopped it up in a VIP area until Wale realized it was almost time to perform. "You tryna go on stage?" he asked Dame. The new pride of Oakland hoops immediately accepted.
A couple of seconds before Wale walked on stage, he posed another question to Damian, misjudging the heart of his 6'3" homie. "You wanna rap?" Wale asked. Without giving more than a second of thought, Lillard shot back: "Yeah! You give me the mic and I'll rap."
Taken aback by Damian's fearlessness, Wale felt he needed to save his buddy from his own excitement. After all, an NBA player dropping struggle bars in front of a Bay Area hip-hop crowd could make for some lasting internet shame. "Nah, I ain't gonna put you on the spot like that," Wale concluded before walking on stage. A disappointed Dame followed.
That was the summer Lillard decided to take his rhyme skills public. After a historic first pro season where he drained more threes (185) than any other NBA rookie prior, the Weber State alumnus found himself once again an underdog.
Three months later, he created #4BarFriday, an Instagram hashtag-turned-website for MCs to showcase snippets of their rhyme skill. Three years later, he released his debut album, The Letter O, featuring hometown heroes like Raphael Saadiq and rap superstars such as Lil Wayne, to critical acclaim. But it wasn't enough.
While last year's The Letter O solidified Dame D.O.L.L.A as the undisputed best lyricist in the NBA, it was essentially a pricey passion project. Aside from a couple of big media interviews with Sway In The Morning and this very publication, the new spitter had minimal push.
"We didn't take all the steps for it to go where I would've liked to see it go," says Dame, seated today in a B/R conference room, nursing a head cold with hot tea. "So that's what we're doing now. I want to do it like any other artist. It's more of an investment, but the outcome is better because you touch more people."
So Damian set a new goal: Create a follow-up album that disrobes the MC of his jersey and showcases him as one of Oakland's finest. First move was to place a battery in his back. That battery was really a chip on his shoulder—a now-integral accessory on the scoring titan's armor.
Dame has been slept on during every pivotal stage of his life; so much so that he now needs the doubt for fuel. "I automatically told myself that people are gonna think I can't top the first one," he says. "People were so ready to give me credit for putting out an album, no matter how strong or weak it may have been. I wanted it to be critiqued and for people to like it for the music, not for the person that put it out."
Dame pauses, lifts and sinks his teabag into the warm paper cup, then says, "Yeah, it might be me."
Summer '17 was a historic NBA offseason. LeBron James called it "the best" ever. Olympic gold medalists played musical chairs to solidify their participation in the upcoming season's Superteam Bowl—the highlight: LBJ’s losing the best point guard in the East and then reuniting with Dwyane Wade.
Once again, Lillard is an afterthought. His Trail Blazers finished 2016-17 41-41—literal NBA mediocrity—before being catapulted out of the playoffs for the second straight year by the Warriors. Damian knew it was time to step out of his comfort zone. He had little choice but to embrace the nouveau role of an NBA franchise player and join the recruitment dance.
"If somebody is interested in Portland, I want to make sure they have my blessing, especially if it's somebody that I want," he says, gripping his tea with both hands. "But I don't think I will ever be the guy who tries to convince someone who has no interest in Portland."
With the Trail Blazers' frontcourt thin on reliable scoring and Draymond Green owning it for consecutive postseasons, Dame knew a perfect addition to he and CJ McCollum's top-five Western backcourt would be one of the world's toughest stretch 4s. So he dialed the cell of Carmelo Anthony, who spent his offseason morphing his unwanted Knicks persona into new alter ego, "Hoodie Melo."
"I said, 'I know you're my type of dude,'" Lillard says. "'Because the Knicks organization was saying all this stuff about you to the public, and…' it was just how he handled it. He didn't shoot back. He just played it how I would've played it. Watching that situation from afar, it just told me a lot about him."
Two weeks later, Melo joined Paul George and Russell Westbrook in OKC, potentially sentencing Portland to another uphill regular season and early playoff exit. Although Lillard has been critical of guys like Kevin Durant switching teams in the pursuit of rings, the callousness of NBA capitalism has softened his stance.
"Look at what just happened to Isaiah Thomas," he begins. "How can teams or owners complain when a dude was All-NBA, [third] in the league in scoring, and you just trade him? And he's a good dude! Then, it's just business we got to accept. But when we decide to pack up and go somewhere else, we're not loyal. Who is really loyal?"
Dame makes eye contact as if the question weren't rhetorical. Then he brings it home. "I'm loyal to Portland. I want to play my whole career here, but at any moment they can decide we want somebody else."
Rip City certainly needs more addition than subtraction—for the organization and its MVP's sake. It doesn't matter that Lillard finished sixth in scoring last year. As long as the league views Portland as middle class, it will treat its leader the same. Damian now knows the previous few All-Star snubs were just a circumstance of seniority and arithmetic.
"They gotta push someone out," he says. "[The NBA] isn't gonna push out Steph [Curry] or Chris Paul because they respect them too much. They're not gonna push out Russell Westbrook. It's more acceptable to do it to me."
The 27-year-old's maturation then aligns perspective with confidence to locate his silver lining.
"When they compare me [to other point guards], they're not comparing me to nobody else in their fifth or sixth year. They're comparing me to guys in their eighth and 11th year. So, I'm ahead of where I'm supposed to be."
Wale and Damian walked off the Summer Jam stage and headed down an Oracle hallway, where the bill's other acts idled. Trinidad James was there. And J. Cole and Kendrick Lamar, "before they became the main dudes in hip-hop," according to Lillard. The ascending young leaders ciphered to discuss hoops. Everyone was recognized as an MC. Everyone except Dame, and he could feel it. He was in his town, yet he was the foreigner.
Dame's new album is titled Confirmed. It was completed in nine August days that saw Lillard wake up at 8 a.m., work out until noon, shower, eat and hit the studio from 1 p.m. until 3 a.m., before repeating. The composition's aim is to solidify Dame D.O.L.L.A's identity as an MC .
To win in the rap game, the Oaktown product knew he, once again, needed to secure a few Hoodie Melos. It's why Weezy has returned for an encore and killer rookie Nick Grant and trap god 2 Chainz have also joined the Confirmed squad.
Although the album is scored by relatively unknown producers, Damian made sure he brought in the hitmaker for Beyonce, 50 Cent and Chris Brown to do the heavy lifting.
"We needed a record that's going to be huge," says Scott Storch, producer of the lead single "Run It Up" and turn-up "Switch Sides." "A record that's going to have legs and be a poster board…that's going to have energy and can be used for endorsements and NBA-related stuff. Not just something that rappers will like, but the world would like."
While the staff for Dame's label, Front Page Music, mined more success last summer than the Trail Blazers, its franchise player still won't go all Golden State with the features. "I do stuff with people I'm a fan of," Lillard says. "Of course I could get in contact with Drake and say, 'Let's do something'—and I'm a fan of Drake—but there are certain people that I respect to be on a song with."
On his first album, his most surprising guest was Juvenile of original Cash Money fame. He's been a fan since grade school. On the new album, though, he tried to top the previous fandom collab. "I was trying to get DMX, but it just didn't work out," he says without a hint of facetiousness. "I talked on the phone with him. It was weird because he was talking exactly the way you know DMX to talk. He wasn't growling, but he was talking real fast and antsy."
The one that got away this offseason is Dame's absolute favorite: J. Cole. That Summer Jam several years ago was the first time he met and dapped up the Dreamville beast pre-dreadlocks. Yet, after five successful NBA seasons and an impressive debut album, Damian hasn't inspired Cole to share a track with D.O.L.L.A.
"I tried," Lillard says, shrugging his shoulders, staring into his now-room-temperature tea. "And I'm a real J. Cole fan, but I'm never gonna be the one to chase anybody down."
Whether it's for a gold Larry O'Brien or plaque, Lillard knows he can't win it all by himself. He's just committed to winning it his way.