Baller. Rapper. Underdog. Don't Sleep on Damian Lillard

By Bonsu Thompson

Photos by Jake Michaels

October 20, 2016


One night, Damian Lillard found himself standing alone on the streets of Oakland, California. He was waiting for an AC Transit bus at the Eastmont Mall station when he spotted three guys approaching from a close distance.

Eastmont is not an ideal neighborhood to be idle or alone in post-nightfall, but it was the high school senior’s daily transfer home after basketball practice. Oakland High sat on Fourth Street, but Dame lived up on 106th. His varsity team always practiced last––after the freshman, junior varsity and girls squads––so every school night, around 9 p.m., he’d transfer from the 57 bus to the 40 at Eastmont. At night, there was always a rainbow of characters around the station. So Dame paid the approaching males no mind.

That is, until he was surrounded.

“Empty your pockets,” one of the men demanded. Dame, an even 6-feet tall at the time, sized up his aggressors. All three looked about his age. Two were shorter than him. Each was slim and appeared to have not seen the inside of a gym in years. When one of them grabbed Dame’s backpack strap, the local hoops star immediately pushed him off, stepped back and pivoted in anticipation of a brawl.

“I figured I would just try to knock one of them out and the other two—we’ll just see what it do,” Dame remembers. “As soon as I stepped back, one of the dudes whipped out on me and sat the gun right on my forehead.”

Today, Lillard is seated inside downtown Portland’s Rex Production & Post studios remembering the stickup of nine years ago. Scoring the flashback is a lively rap song titled “Roll Call,” which is currently blaring from every corner of a luminous recording room. Dressed in a gray long-sleeved T-shirt, home-cut sweat shorts and his own signature Adidas, the two-time All-Star NBA point guard is on the opposite end of the soundboard earnestly bobbing to the rapper’s flow. “This that neighborhood anthem,” he says to no one in particular. That flow belongs to Dame––Dame D.O.L.L.A. (Different On Levels the Lord Allowed) when Lillard is rapping––and today’s private listening session is for his debut rap album The Letter O.


The Letter O Available October 21 on iTunes, Apple Music, and Spotify.

The album title is a tribute to both the number Lillard wears in the NBA and the “O” that has remained a constant throughout his hoop journey (he’s from Oakland, went to college at Weber State in Ogden, Utah, and now balls for the Trail Blazers of Portland, Oregon). The 2016-17 NBA preseason is just five days away, but at the moment, the former Rookie of the Year’s only priority is making sure his beats, rhymes and life are segregated from Shaq and Kobe and instead classed with Cole and Kendrick.

Yes, he’s a $140 million professional athlete with a chunky Adidas endorsement, but his climb to the top was long, steep, less-traveled and life-threatening. No, he hasn’t slung in a trap––just broken many with court vision and crossovers––but he understands feeling trapped by racism and classism. He understands having to fight and pray then fight again every single day.

“Heavily favored by the man

I'm giving thanks, I raise my hand

He ultimately made the plans

For me to thrive and be alive

I ain't sink, he let me swim

Remember when them lights was dim"

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Damian was born into an Oakland family as large as it is close-knit. A bunch of aunts and uncles make for dozens of cousins––so many cousins, in fact, that playtime with the fam resembled American Gladiators. “It was always a competition for everything,” says Lillard. “Telephone pole races, football, baseball…girls and boy cousins. We was always playing against each other. You didn’t have a choice.”

Lillard stands as one of the more merciless guards in today’s NBA because he was raised to be a warrior, regardless of how diminutive he was or how large his competition. To sever then spike your defender’s head is simply in his DNA. “I been punched in my face. I done lost for a whole summer to all my older cousins. It wasn’t like I could stop. If I didn’t believe it, they was gonna go harder on me. [So now] I think, it ain’t gonna get no worse than that, so it is what it is.”

While his family was competitive internally, against the world, it was a team of one. Each relative receives equal amounts of love and support, through good and bad times. The latter Damian knows much too well. Like when he got suspended for fighting in the middle of his eighth grade year.

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When the news hit, every one of his Oakland relatives met at his grandmother’s house. Each family member agreed to commit to a three-day fast for clear prayer. “My mom was like, ‘You’re a good kid. Don’t let them discourage you. You’re going to make it to the NBA. Let’s pray,’” Damian recalls. “We would be in the car, praying out loud. If I didn’t have that kind of encouragement, who knows what I would’ve thought.”

Damian eventually transferred to another middle school his cousins attended. He graduated onto high school a week later but will never forget the eighth grade. It’s why gratitude is a main ingredient of The Letter O. “It’s important for me to tell that part [of my life],” says Dame, whose appreciation beams brightest on the out-loud prayer “Thank You” featuring vocalist Marsha Ambrosius. “Because if a parent is listening they might understand the value of what it could mean to [support] their kid.”

“I’m like a product of poverty and a prodigy

My private school coach said I couldn't, what a hypocrisy

Obviously, I'm built like no other, it ain't no stoppin me”

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After escaping the eighth grade, Damian was sent to Arroyo High School. Although the suburban school’s student body was predominantly white, life for the freshman didn’t require a huge adjustment. He played varsity at 5’5”, one of only two black kids on the roster. His coach was new, black and aware that his best player was also his youngest. So he gave Dame the playing time needed to procure wins. “When [the coach] came on he kind of nigga’d the program up a little,” says Lillard. “He was letting me come down and hit pull-up threes. Screaming after I hit a couple in a row. He let me go.”

Although the Arroyo team became more competitive, the blacktop bite Dame played with wasn’t received well by his teammates’ parents. More tick for him meant a lot less for their sons. Players began quitting in the middle of the season. The coach was eventually fired. The situation was clear to Dame: He knew he couldn’t return to Arroyo.

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For Lillard’s sophomore year, he transferred to the powerhouse program of St. Joseph Notre Dame, most famous for producing Jason Kidd. Once again, his Oaktown roots would work against him. St. Joe’s was a prep school with a men’s basketball coach, Don Lippi, who wouldn’t warm up to Damian’s fire. “I was one of the better players,” Lillard remembers, noticeably still unsettled by the memory. “But the coach had an issue with me like, ‘You’re too aggressive, and you talk trash.’ I didn’t talk trash like that, but if I block somebody’s shot, ‘Get that shit outta here.’ If I do a move and score on you and I’m running back and you in the way I’m gonna bump you. I’m like, I’m not the problem. These niggas need to get tougher.”

More so than his aggression, the then-5’5” PG’s biggest obstacles were the three senior guards playing ahead of him. So he rode the bench all season. The camel’s spine was severed during the final sit-down between Dame and Lippi. “We have a meeting, ’cause he meets with all the players at the end of the year, and he’s telling me how I might not be on the team and I’m gonna have to really earn it. He asks me, ‘What do you want to do?’ I say, ‘I wanna play in the league.’ So he goes, ‘One second,’ pulls out a notepad and says, ‘This many kids play college basketball. This many play Division I. This many play pro. This many make it to the NBA. You really think you’re gonna be a part of this?’ So I’m looking at him like, Wow, that’s cold. Like, even if I’m not gonna make it to the NBA, you’re not supposed to tell me that.”

“I say that to everybody at 14 years old,” Lippi says today. “Because everybody thinks they’re going to be in the NBA. But Dame would’ve been our starter the next year. That wasn’t even a question. There were three seniors ahead of him, and they were all graduating. He was the best guard coming back.”

Today, Lillard and Lippi’s accounts stand incongruent. One fact is clear: During that meeting, 15-year-old Dame had reached his threshold. “I straight went home to my dad and was like, I can’t go back there,” says Lillard. “He didn’t fight me on it at all. So I transferred to Oakland High, and I was on after that.”

The morning after the Letter O listening session, a B/R Mag photo crew awaits Damian’s arrival inside Portland’s historic Crystal Ballroom. At the top of the 102-year-old performance venue is a mezzanine with descending theater seats. The lower level offers enough space for 1,000 people and a stage that’s been graced by greats like Jimi Hendrix, the Grateful Dead and Marvin Gaye. Damian also rocked it last July (on his birthday) during his first rap concert. Today, the stage floor is wide-open, bare and mocking the science that heat rises. Lillard walks in with his arms stuck to his sides as if he’s trying to keep what little body heat he has stored. He’s already styled for his photo shoot. Aside from white-and-black-striped shell toes, he’s rocking all black. The rapper is clearly still with us. Then again, D.O.L.L.A. has always been here.

While a star at Oakland High, Damian played alongside his closest friends, Drake, Drill and Pee. For two years the band of brothers wrote and recorded the songs they ran out of the locker room to. When the four went off to college, they came home every summer and made mixtapes to the hottest beats out. You can hear Dame’s childhood influences throughout The Letter O: a reclined, slick-tongued T.I. on the Jamie Foxx-featured “Plans”; a brash, transparent Tupac heard on “Bill Walton”; and, like Kanye, the heart to go toe-to-toe with Lil Wayne on “Loyal to the Soil.” From his wonder years up until today, Dame has been drawn to MCs who not only stack stanzas like Legos, but simultaneously build up their listeners.

“J. Cole’s my favorite right now,” says Lillard, after his photo shoot, now seated up in the third row of the empty mezzanine. “I been on Cole since ’08. I was telling everybody on my team, my roommates, ‘You gotta listen to this dude’…but they wouldn’t listen. Then Jay Z came out with The Blueprint [3] and [J. Cole] was on “A Star Is Born.” Then they was like, ‘This dude here is nice,’ and I’m like, ‘That’s J. Cole!’”

“Thoroughbred and I’ma force

And built to stay the course

Dolla: You gon’ respect it

You gon’ respect it
You gon’ respect it

If you don't I wish you blessings...”

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Dame’s new rap career will inevitably receive criticism of both the constructive and hatin’ persuasion. Rap lines of NBA players have historically made the author the punchline. Even Dame’s management team couldn’t believe that after a historical NBA debut, all the point guard could think about was informing the world of his rap skills. “I was a hater,” says Nate Jones, an agent at Goodwin Sports Management who now leads all things music-related for Lillard. “There was no way someone that good at basketball could be a good enough rapper for the public to react to it positively. And it’s not like when Shaq released his music and he only had to deal with traditional media critics. Everyone has social media these days. Fans are looking for reasons to throw a Crying Jordan face on you!”

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But then in 2013, D.O.L.L.A. created along with the Instagram account and subsequent hashtag. The goal was to gift aspiring MCs a digital platform (71,000 followers today). On the eve of the 2015 NBA All-Star Weekend, he did what most NBA players wouldn’t dare and many rappers can’t: kill Jay Z’s “Dead Presidents” instrumental on Shade 45 SiriusXM’s Sway in the Morning show. Sway titled the video “Damian Lillard Is The Best Rapper In The NBA” and it garnered 600,000 views in a matter of days (today, over 6 million). “There's no law that says you can't be both an athlete and MC,” says Sway Calloway. “It's just that normally the great athlete is a wack MC. When I first heard [Dame] rhyme I was pleasantly flabbergasted, and it kept getting better. I knew in the end he was a student of the culture.”

Rest assured that Dame D.O.L.L.A. is no A.I. or C-Webb or, even, Diesel with the pen. Just check him belie rookie rapper status with impressive storytelling on the collegiate biography “Wasatch Front.” But is being the best rapper in the NBA enough to win over hip-hop? “I watched [HBO’s] Any Given Wednesday with Nas and Kevin Durant last night,” begins Lillard, staring over the balcony as the photo team packs up. “[Bill Simmons] asked Nas who’s the best athlete to ever rap and he was like ‘Shaq’ cause Shaq had a platinum album. As far as ability, I know I’m the best hooper to ever rap. But KD was like ‘Dame Lillard.’ So when I come out I guess we’ll see.”

“We are never going to change the fact that he is a basketball player first, nor do we want to,” says Derrick “Lotto” Hardy, The Letter O’s A&R and a former music exec at Motown. “But we do, however, want Dame to get respect in the music industry by his peers. I think...better yet, I know we accomplished that.”

“All-Stars, I should have three by the name

They say I cried about not makin’ it, it's free to complain

It's deeper than fame... It's principle

My feelings hurt? Minimal”

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Although Lillard is kicking at the door of NBA superstardom, he still feels like that high school sophomore fighting to get on court. Or that eighth-grader fighting a suspension. Or that senior who almost had his brains blown out at a bus station over $20. Yes, he’s technically a two-time NBA All-Star, but the Gary Payton descendant feels more like a 1.5. Many were shocked he got snubbed from the 2016 big game. Mainly because by February his numbers were top 10 in the league and the Blazers had playoff position. Partly because he was selected the previous two seasons. Truth is: If Blake Griffin hadn’t been injured for the 2015 game, Dame would’ve gotten jerked consecutive years.

“I’ve always felt slept on,” he says, shaking his head before making direct eye contact. “I’m out here averaging 25 points, seven assists and almost five rebounds. That’s an All-Star. And not just All-Star numbers, but who you should want to represent your league as an All-Star. I’m an all-star as a Global Ambassador for Special Olympics. All-star with an anti-bullying campaign. An all-star in the Oakland community. An all-star in the Portland community. I’m an all-star for parents who want their kids to pursue a college education. I’m a college graduate! I don’t brag on that stuff, but we talking All-Star.

“I earned this.”

If there’s anything apparent while listening to Dame, the rapper and baller, it’s that he always remembers. As a senior at Oakland High, he returned to St. Joe’s and torched his old team, making sure to address his former coach on several trips back down court. Similarly in the NBA, it was Portland’s first game after last season’s All-Star break, serendipitously against the Golden State Warriors, where Lillard made it his mission to do what he’s done most of his 26 years on Earth: prove people wrong. The result was 51 points (9-of-12 from three), seven assists and six steals on the head of Steph Curry and a 32-point drudging of the champs. “That game was definitely like, Aight, if this is the MVP and the All-Star starter at my position, I’m gonna come out and take this one personal. If I don’t come out and score 50, I’m gonna be 2-for-29. We gonna settle this right now.

That vengeance carried over into the second round of the playoffs as Lillard kept the Warriors quite nervous with astounding exhibitions in Games 3 (40 points, 10 assists) and 4 (36 points, 10 assists). He shines most in the moments that make diamonds. Discomfort has so often been his norm that it’s almost become a comfort zone. “The pressure was on them because they had just broke the record,” Lillard continues his reflection, more excited than he’s been all morning. Anyone watching from the stage level below could easily mistake his emphatic hand movements for him previewing a new 16. “[I thought to myself], You better not lose to the Trail Blazers! We ain’t got nothing to lose, so I’m gonna go out there and empty the clip.

For once, the baller sounds more gangster than the MC.

Bonsu Thompson is a media and marketing producer who, throughout his 18-year career, has commanded titles such as editor-in-chief of the Source, creative consultant for MTV2, executive producer of’s PRELUDE series, SLAM Magazine senior writer and music editor for XXL magazine.

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