Derrick Coleman—the rapper known worldwide as Fredo Santana—had a lot to look forward to. His girlfriend had recently given birth to his son, and he'd started a business in California. Though he'd struggled with health problems related to drug addiction, after he was hospitalized in October, he'd given up lean (promethazine/codeine cough syrup) for good. (After the New Year, in a comment on the rapper Mozzy's Instagram, he remarked that he was nearly 60 days clean.) When he was found dead in his Los Angeles home Friday night, he was only 27 years old. His passing was undeniably tragic; on twitter, he'd explicitly linked his drug problems to a method of coping with trauma he'd suffered in his past, and much of the public conversation around his death focused on the way the forces of addiction and trauma shaped his life. Yet the outpouring of emotion from across the hip-hop world, from 50 Cent and Drake all the way to rivals from his own city, suggest his story meant more to them, that it was not defined by the darkness that once surrounded him.

At one level, it's difficult to reconcile his health problems, and the very human weakness they reflect, with his powerful public image. Lil Reese's infamous lyric on Chief Keef's "Don't Like" compactly intuited Fredo's role in the group. "Fredo in the cut, that's a scary sight!" resonated because it captured an elemental truth of Fredo's fearsome public persona, his embodiment of strength and loyalty, and a sense that he was the crew's protector. It was also based in a real familial dynamic; when his 16-year-old cousin Chief Keef blew up, Fredo Santana was a relative elder at 21, and he'd embraced the role well before their fame. "He was a very stand-up dude," says DJ Kenn, the producer who lived around Keef's family from 2008 and recorded Keef and Fredo's earliest music. "Getting paid and giving money to his family, trying to survive. He'd been like that, before the rap shit. He's got character. People looked up to him."

Calling Fredo a "rapper" sells him short, not because the title can't be a worthy honorific in the right hands, but because Fredo's notoriety came as much from the character he played as the music itself. He was a cultural icon in the classic sense, immediately recognizable for the trademark cross tattooed on his forehead, and developed his own cult of celebrity independent from his crew. He also, more than the others, made it publicly evident he was self-aware about his persona. While Keef played the enigmatic auteur, a distant center of gravity unto himself, Fredo was more of an affable networker. Though he retained his fearsome reputation—just ask the Migos—his warm personality gave his celebrity dimension, particularly for a street rapper, who outsiders tend to flatten into cardboard archetypes. He also stepped outside the Glo Gang's immediate circle, recording with everyone from Texas rapper Maxo Kream to Kendrick Lamar. He even appeared in Drake's "Hold On, I'm Going Home" video, his cameo as a kidnapper as knowing as the video's action film pastiche.

Still, Fredo was not unskilled as a musician, even if his proximity to the talents of Keef, Reese, and Lil Durk helped elevate his sound. As a role player, he added an essential element, his brute-force bars operating as a blunt instrument, their firmest connection to a rough-hewn street aesthetic. In the right context, he shined: his gruff vocal style worked well on choruses, its rugged, world-weary timbre a distinct graphite brush, as on Lil Durk's thunderous "Wild Niggas" and King Louie's swirling "Numbers." On Lil Reese and Lil Durk's "Beef," Fredo steals the show, his brash non-rhyme "run up on you with that fucking pipe!" short-circuiting poetics to convey a violence that couldn't be contained by formal rules. Fredo was not the best rapper in the crew, and his best work was often in collaboration with more sophisticated songwriters; while Keef artfully negotiated the tension between intuition and craft, as a rapper, Fredo leaned amateur. Yet it was this nonprofessional spirit which made him the concrete-block spiritual heart of GBE.

This stripped-down brutalism was no doubt in part what drew the attention of Prodigy from Mobb Deep, who tweeted out Fredo's "My Lil Niggas" when it was released on WorldStar in 2012. Prodigy's approach to hip-hop had a parallel impact on the genre in the mid-1990s, its severe, unyielding bleakness an aesthetic avenue approached via reduction rather than amplification. But Mobb Deep's music was harder than everything else because it was pared-down and terse, withholding from the listener. Keef and co.'s approach, by contrast, was a rawer, degraded version of the hits emanating from the South, where Lex Luger-style Bangers ruled. The rapping was off-beat, and the desiccated bangers soon melted further into amorphousness post-"Love Sosa," or cranked to the skittering, nervous tone of G Herbo and Lil Bibby. For the drill scene, what godfather King Louie called the city's "gumbo" of national influences cohered in the GBE crew as a popular sound eaten through as if by termites.

In New York, where Southern acts struggled to maintain a foothold, this Southern-via-industrial midwest style made more sense; it likewise picked up throughout the country, in cities which had previously shown allegiance primarily to Atlanta. Suddenly, the rest of rap felt overly smooth and commercial in the contrast. Drill music's off-beat flows, some argued, were mere evidence of its not-ready-for-prime-time status. But within hip-hop, the imprecision of its sound was a selling point; here was a style that better represented what was really going on, independent of the industry politics and professional A&Ring, accessible to any group of kids--and now they were kids, often--with a camera crew. This was music built instead, it contended aesthetically, through an organic connection to its communities, to the streets. Fredo's rough approach wasn't interesting because of a lack of ability, but as a reflection of an artistic turn to an organic underground, to the cultural source.