From the West Side with Love Saba is bringing West Side Chicago to the world.

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Photography By Azha Luckman

His lanky frame draped in orange Gore-Tex, dreads swaying in front of the crowd at San Francisco’s Social Hall, it’s hard to tell that Saba’s the quiet, introspective type. On stage, the Chicago spitter exudes charisma and honesty, confidently pausing his set to break down the realities of independent artistry with his audience.

“I brought Pivot Gang, my literal family, on this tour. I’m only able to do that because of you guys. The only money we have is the money you give us, so thank you.” A smirk creeps across his face, as a crumpled dollar bounces off his soles. “Why you gotta make me feel dirty like that?”

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The morning before his show, he’s more subdued. There are no fans in these streets, no one to perform for, and it’s clear this cracked cement feels closer to home. Liquor store, church, pothole—this west mirrors the one that raised him, that he had to leave to write his new album, Bucket List Project. A month holed up in an L.A. apartment with his close friends and collaborators NoName and Phoelix gave him the clarity he needed to view his home more reflectively.

“Being away from the West Side, I was able to speak on exactly what I felt about it. What made it different and how it affected me. I needed to get away from the hot shit, the wild shit to see the little truths. Like shit, [in Chicago], we don’t have no fucking mountains, no fucking hills. That could be a song right there, because it’s simple and the truth. But you only see that when you’re here.”

Sun parts the overcast skies during a brief trek through West Oakland. Saba, his manager Cristela, and his DJ Dam Dam trade stories from their first headlining tour. We stop at a cafe where Saba orders a chai, then slips outside to bask in the fresh air and reflect.

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“Good night, bad night, whatever—being here is a blessing,” he tells me. His mind is clear, focused less on the experiences, and more on the experience. “I’m able to bring Pivot, my literal family, on this tour. A lot of artists don’t get to do that for years. We sold out Seattle; I’d never been to Seattle, that’s a crazy feeling. This whole shit is a blessing. I don’t have any other words for it.”

On the surface, Saba’s quiet demeanor is a contrast to his high-energy onstage persona, but the silent poet is ever observant. That attentiveness is the fuel for Saba’s writing, rhythmically complex flows full of detailed observations. The effortless melodies Saba seems to pull out of thin air are truly the product of studying his father, a singer, during studio sessions in grade school. Over the last few years, Saba has risen to the top of a crop of young black Chicago artists who channel that same soulfulness in their work, landing on Chance the Rapper’s landmark Coloring Book and culminating in the release of Bucket List Project late last year.

Although young, the 22-year-old is not blind to the importance of his experience. Though national attention on Chicago often focuses on the plight of South Side, as many of the city’s idols call it home, his neighborhood of Austin, and the West Side in general, faces the same issues, but has fewer recent success stories.

The neighborhoods west of the Chicago River are bursting with forgotten stories. The West Side has a history of social activism, a response to decades of institutional racism, redlining, and intentionally oppressive urban planning. Fred Hampton helped to build the city’s chapter of the Black Panthers in the late ‘60s before paying for it with his life. Today, the area is affected by the city’s ongoing epidemic of gun violence, but also by a new wave of gentrification.

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Despite changing demographics, the blocks west of the Chicago River are a land of last names and family trees. Saba’s lineage is an exceptional example. His mother and grandmother are both Austin natives and still reside there, yet his father left for New York City to pursue his career as a vocalist. Through his own music, Saba has transformed himself into the closest thing to a current spokesperson for the area, spreading his infectious optimism and the knowledge gained from his travels with his people. He even featured the West’s last role model, Lupe Fiasco, on Bucket List, where he shared his desire to win the Nobel Peace Prize.

“It’s really easy to feel trapped in my neighborhood because a lot of the people have been there for generations. If nobody on your block has been to California, what makes you think you can go? That is a very pessimistic way of thinking, but it’s also a reality for many people Chicago. My dad damn near brainwashed my brother and I to be optimists, to believe in ourselves. [After he moved to NYC], he’d call and before I could hang up, I’d have to tell him ‘I’m a winner, a leader, a strong black man and an original man.’ He had us taking risks, trying to pursue our dreams before we were even 10.”

His father’s mantra still guides Saba through life, and over a decade and a half of relentless creation, he has transported himself from a bedroom studio, posting beat tapes and praying for plays, to Late Night with Colbert alongside fellow Chicagoan Chance the Rapper premiering “Angels.”  The partnership was long in the making; both spent countless hours attending Young Chicago Authors and You Media, the hallowed open mics that serve as talent incubators for the windy city.

Pivot Gang cut their teeth on these stages, and their practice shows. Under the San Francisco spotlights, his crowd control is impeccable, their energy in the palm of his hands. On his command, they jump, they laugh, they shout. Their unbridled excitement grants him the freedom to explore the more melodic corners of his catalogue. “I’m about to do some completely not hip-hop shit, but I don’t give a fuck because it’s my show,” he quips before members of Pivot’s self-proclaimed boy band Joseph Chilliams and Squeak join him as interpretive background dancers for “Symmetry.”

“I don’t know how people do [music] without having a team they consider family. When we started Pivot, it was a lot of literal family. Me, my brother, my cousin. Everybody else who wasn’t related to us had been around for close to 10 years now, so it’s still family.”

Hours before his show, Saba finds himself seated at Lake Merritt, enjoying a brief respite from the cramped tour van. A frequent Bay visitor, he is no stranger to its marshy shores, but he’s visibly surprised by the new number of bodies enjoying the updated amenities. His phone rings twice, a FaceTime call from his Chilliams and Squeak, whose flight just landed at SFO. Their animated conversation displays his anticipation. He can’t wait for his brothers to join them.

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A pensive moment follows the conversation. He pulls his knees to his chest, as he surveys the hills before him. His denim jacket draws taut the words embroidered across his shoulders: “Long Live John Walt.” Beneath lays a needlepoint portrait of his cousin and Pivot Gang co-founder. The stitches are fresh. Just weeks ago, Walt was senselessly stabbed and killed after a verbal altercation leaving a Downtown Chicago train station. During his performance, Saba dedicates “Church / Liquor Store” to his memory. The words, inspired by a bus ride home through his city forgotten, seem to hold more meaning now that they reflect the fate of his own blood.

“Bad habits of wrong places at wrong times

A stray bullet’ll take your first-born like the Tenth Plague

I’m the new Pharaoh

My phone line forever open for prayer

The fallen soldiers ain’t fell, they in my pen

And I do thank God.”

The fallen weigh heavy on his conscience, but in crafting his own soundtrack to his city, Saba’s found both a personal escape, and now his livelihood. Still though, processing life experiences and gift wrapping them for an audience brings its own set of challenges. “I’ve been in a weird creative space, but this tour is helping it die down,” he tells me, eyes slowly scanning the passing faces at the lake. “I’m just excited to sit down with Phoelix in the studio. I finally feel ready to get back to work.”

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Raised on Zachary's slices and Mango Habanero sausages from Top Dog.