Watching Saba tower over his packed New York City crowd, pouring his soul out through the speakers, it’s hard not to smile. He’s clearly doing much more than making a name for himself as an emerging artist, even in the midst of insufferable loss. The 22-year-old Chicagoan from the categorically violent West Side has been dealt a rough hand. But once his fingers tighten around the mic, he triumphantly is rewriting his story, one bar at a time. 

Saba (born Tahj Malik Chandler) stands at the center of the dimly lit stage at Webster Hall on an unassuming Wednesday evening. Bursts of booming bass, laced with chants from the crowd decorate the venue walls, as Saba punctuates the ambience with lyricism trembling through half-full plastic cups of PBR. The whole scene commands all sorts of shaky-yet-determined smartphone documentation. With a vibrant assortment of curious 20-somethings and day-one devotees taking the lead songs like “Monday to Monday,” “The Billy Williams Story,” and “World in My Hands,” it was clear that these are the exact moments Saba has been chasing.

Along with his trusty affiliates and collaborators—a close-knit group of like-minded musicians known as Pivot Gang—Saba embarked on his first-ever headlining tour earlier this year: a 19-date trek scattered with boundless reaffirmations that years of hard work are finally paying off.

“I think we had a moment every night, before the show or after the show, where we’d just be looking at each other, like damn,” Saba later reflects back home at his grandparent’s house in Illinois. “Our jaw was just to the floor from being in awe, every night, in whatever random city we’d be in.”

The promotional run for his debut studio album, 2016’s Bucket List Project, turned into a movement—with bright-eyed fans swarming Saba the second he stepped off stage, hopeful to get the opportunity to talk his ear off about what’s on their own bucket list and how his music deeply resonates with them.

Much to the delight of those in attendance, Saba stuck around, happy to listen and entertain. Even the security team in New York permitted the sold-out affair to stretch well over its allotted time so grinning, sweaty fans could get their handshakes and thank yous into the single-digit hours. With the tour’s magic indisputable, reality hit once the music fades: none of this almost happened.

Two weeks prior to hitting the road in mid-February, Saba’s cousin Walter Long, Jr.—a member of Pivot Gang who released music under the monikers John Walt and dinnerwithjohn—was fatally stabbed during a fight on the street in Chicago’s River North neighborhood.

The heart-shattering news was, at first, enough to have Saba reconsidering going on the tour entirely, something he divulged to a sea of onlookers during the New York pit stop. While running through his catalog, his raw, emotional ad-libs couldn’t completely veil the fact Saba was rhyming through heartbreak. But still he pushed on, turning the piercing pain of losing a squad member into eternal motivation to continue working toward the vision they shared.

“[The tour] was the most special thing I’ve ever witnessed in my entire life, especially because of my cousin,” he somberly admits. “Walt was supposed to be on a lot of those dates with us. We were all in a really weird emotional space. But we were so blessed to be there at all.”

While the shows were full of scenes straight out of a movie that Joseph Chilliams (Saba’s older brother), MFN Melo, and Miami’s Sylvan LaCue all experienced together, the grim reality is that they haven’t been able to properly grieve through the past few months’ calamity and chaos.

“It hasn’t really processed, since we’ve been gone so much, but it’s been the most beautiful last few months of our life, and I know Walt has everything to do with that,” Saba explains. “We’re trying to get a foundation and scholarship set up. Every day is weird but we are pushing through it. We’ll make it happen one way or another.”

Following his untimely passing, Walt’s presence hasn’t dissipated. With conviction, Saba’s actions promise it never will. Leading the audience in a memoriam chant rattling louder than some of the set list’s most passionate and catchy hooks, the Pivot Gang’s visionary leader repeated Walt’s name into the microphone until his voice began to wear. While sporting his signature beanie atop his shoulder-length locs, Saba also donned a light blue denim jacket adorned with an embroidered portrait of his cousin. With the cursive words “Long Live John Walt” beautifully stitched on the back, Saba wore the custom threads with pride, carrying the reminder that those who you love never truly leave you.

“It’s so weird to even have to think like, yeah, I am keeping his legacy alive,” Saba says, his voice tender from fighting the urge to shake in disbelief. “We played basketball yesterday and that’s how he got his name, from playing ball in high school. I do very much feel his presence in everything we’re doing.”

Saba is wise to combat every heartbreaking setback hurled at him by turning to his music. Arguably, such is par for the course for those growing up in a city that has long been tied to its reputation of being plagued by senseless violence, experiencing over seven hundred murders in 2016 alone.

“Everyday somebody you know is gone, or somebody you see every day is gone,” he says. “It’s crazy difficult to be in that and to keep to yourself in hopes that things will change.”

Despite his story being lined with loss, returning to the soft-glowing optimism buried beneath his hardships is very much an integral part of Saba’s character. No stranger to receiving stomach-churning phone calls that can permanently change his world, Saba is fully aware he hasn’t had an easy ride. But he doesn’t let his tragedies constrain him, either.

“Shit is hard,” he says. “Everyday somebody you know is gone or could be gone. The amount of shit you go through living in Chicago as a young person is crazy. It’s just a place where you never know on any day what that day is going to look like, what’s gonna happen, what call you’re gonna get.”

While Pivot Gang found inspiration for its name in a classic episode of Friends (the one where Joey and Chandler help move a brand new couch up Ross’s humorously narrow stairs), the wisdom to keep moving forward was born out of a place of survival, particularly after experiencing death.

Months before Saba released his second mixtape ComfortZone in 2014, his uncle unexpectedly passed away in his sleep, doubling as a wake up call to create with intention and urgency, further proving the mantra behind their moniker is reinforced daily. When one chapter ends, another has to begin. No person or city is exempt from that, although Saba knows Chicago may be more accustomed than others.

“Chicago is the most beautiful city that I’ve ever been to,” he elaborates, not allowing his hometown’s rough edges to detract from its potential. “I think that’s the thing that a lot of outsiders don’t get. I used to have an answer in mind regarding what the city needs. It needs so much help. But I do know there are a lot of artists in the city that are changing Chicago and saving Chicago. That’s one of the things I’m most proud of.”

The fact that the days aren’t promised was further augmented at the top of this year, when Walt called him to reveal that he survived an entire clip being emptied into the side of a car he was in. Such gut-wrenching events are etched into the increasingly common picture of what it’s like to grow up in Chicago. Knowing this all too well, Saba leaves himself no choice but to keep his inner turmoil at bay and look toward the light. This very concept is etched into every song on the Bucket List Project, and is one he keeps close to his chest.

Navigating through a path littered with the uncertainty that life’s next cruel plot twist could be lurking around the corner, Saba’s courageous perspective is lauding him as one of Chicago’s most promising upstarts. From performing at open mics in Wicker Park as a teen to gracing the stage of the Late Show with Stephen Colbert in 2015 alongside Chance the Rapper, the growth that he has experienced is an inspiration.

Such unfiltered tenacity shines through his catalog, and in embracing his story over a refreshingly eccentric neo-soul-meets-rap-inspired soundscape, he’s winning over a widespread audience. In 2013, his first collaboration with Chance the Rapper, “Everybody’s Something,” helped elevate him to a new level—with eyes fixating on Chicago’s prospering rap scene in ways they haven’t since artists such as Kanye West, Common and Lupe Fiasco first put on for the city and garnered national attention. After collaborating with artists such as Mick Jenkins, Taylor Bennett and Eryn Allen Kane, Saba reunited with Chance, creating 2015’s “Angels”—a track that has since seen over 70 million streams on Spotify.

“Every year has been better than the last,” he exclaims. “Making beats for my brother and his friends when I was 13 was one thing, but I had to really step my game up. Now everybody is still trying to out-rap everybody, but those early competitions had a huge effect on what my everyday life is like now.”

From Chi-town legend Twista to industry mainstay Sway Calloway rooting for him, Saba’s new normal includes Chance showing up as a surprise guest during his most recent headlining set, seeing his name selected for The Source’s coveted Unsigned Hype column and landing a nomination for XXL’s 2017 Freshman Class. Despite this growing list of accolades, Saba is trying his best not to get his mentor, FRSH Waters, too excited.

With their friendship dating back to when Saba was 13, FRSH helped put Pivot Gang on the map over five years ago, even guiding Saba to the right rooms to introduce him to Chance and Noname. After getting into some legal trouble, FRSH has since assumed the temporary role of being the group’s unofficial head coach, offering sage advice from behind bars.

“It’s been kind of crazy because he hasn’t been able to see what something he started has turned into,” Saba says. “We try to downplay everything so he doesn’t feel like he’s missing out on too much.”

With more people to make proud than just himself, Saba’s optimistic spirit is taking charge. As he rises as Pivot Gang’s rightful leader, it’s hard not to see how his path mirrors that of Chance’s, whose ascent to stardom stemmed from his early work with his former Save Money crew alongside Vic Mensa.

Although the Pivot Gang has been home basking in their recent triumphs, they haven’t slowed down. A tireless Saba is no exception, performing an assortment of one-off shows at various colleges and already diving headfirst into his next studio effort. His hunger is also presenting him with options for his first real apartment, with the support of his loyal legion of fans affording him the luxury of being able to leave his childhood home.

“I’ve never moved in my entire life so this will be a big deal,” he says modestly. “I’m so excited to have my own thing. I’m trying to make sure I have at least two bedrooms, one for my bed and I want to have a studio in the other room, so we’ll see how that goes.”

His preferences for where he wants to live are strikingly minimalistic, such as requesting natural light and solid neighborhood food options. True to form, Saba’s priorities lie within his music.

“I built the studio in my basement now, and it’s been down there for years and years and years,” he says, detailing his plans for his new studio. “I’m excited to start from scratch and see what it turns into over time.”

While going through what accumulated in the same studio he recorded his first project, 2012’s GETCOMFORTable, Saba struck gold. During the coming-of-age cleaning process, he unearthed a dust-covered box full of cassettes he recorded when he was a young boy.

“I haven’t even listened to them yet because I don’t have a cassette player,” he says. “They’re just sitting there, waiting to be heard. I’m sure some of them are terrible but there could be some gems, too. I kind of remember them being fire…”

With the potential behind those sonic treasures staring him in the face, so is the reminder that his cousin isn’t there to listen along with him.

“I’m still adjusting,” Saba says, glancing at the material possessions peppered throughout the family home. “When I look at the refrigerator here, there are photos of us when we were little and an emptiness kind of takes over my whole body in a way. When I go to the basement where the studio is, he was there with me the day before [he died] so like his hat’s down there and a bunch of his random shit. You know, stuff you wouldn’t take with you if you knew you were coming back the next day.”

As he carefully inspects his belongings and Walt’s, Saba is at an unavoidable turning point, and a heavy one at that. He’s now able to turn his passions into a paycheck, but being tasked with these acts of growing up aren’t burdens made totally easier by his newfound success. However, the promise of a new home base and the months ahead are tipping the scale away from the darker side of Saba’s truths.

“I’m keeping open-minded,” Saba says. “I’m excited to tour again. I don’t even want to be home right now. I’m just going to do everything in my power to keep this momentum going and keep everything we’ve built alive and strong.”

While checking out apartment listings, Saba’s mind can’t help but wander back to FRSH and the brighter days awaiting them both.

“It’s so close to him being able to come home and see for himself,” Saba says, explaining that he recently received a letter from the prison detailing that FRSH’s sentence is slated to conclude this Summer. “I can’t even begin to tell you how excited I am. We’re just going to lock him in the studio and turn him into Future and make him do like 80 mixtapes.”

As Saba keeps watch on the horizon and eagerly reviews the blueprint plan of attack FRSH drew up from prison, his music, his determination and his family—in blood and in brotherhood—are all he has. And for Saba, that will always be enough.