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.
Listen to DJ Amaris’s mix, ‘The Best of Fredo Santana’
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.”
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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.
Of course it wasn’t just the sound of the music that had changed. This was social media and YouTube disrupting the music industry at both a local and national level, a great leveling as a few tech companies eliminated entire label departments and swept away local jobs and profiteers alike. Adjacent but apart from music, social media fanned the flames of gang conflicts and created new ones, and opened a window into that world which outsiders could exploit. Rappers became scapegoats for this sudden change in terrain. An early fascination with Chief Keef by the mainstream music press quickly reverted to a safer norm when harsher realities intruded. This left a void for this new generation of artists, including Fredo, who were exceedingly popular online, yet, pre-streaming services, lacked metrics to validate them to mainstream gatekeepers. Into this space, vloggers like DJ Akademiks made their careers, serving a large audience for these stars with little regard for media industry norms—and a larger appetite for the more lurid aspects of Chicago street culture.
Their marginalization from mainstream media outlets reflected a wider pathologization of the artists, which had real-world consequences for their bottom line, and Fredo’s ability to develop a legitimate career as a businessman. In a piece published in The Triibe after Fredo’s passing, Merk Murphy, who has worked with GBE’s management, argues that it was this work that should be Fredo’s legacy. Under the auspices of public safety, the City of Chicago barred drill artists from working in their hometown, going so far as to prevent a hologram of Keef from “performing” even in neighboring Indiana. Whether or not Keef’s own safety, and the protection of his own ability to work for a living, was a concern of the Chicago police, may have influenced GBE’s decision to move to California in 2014.
“In L.A., Fredo could be the entrepreneur Chicago wouldn’t allow him and his drill cohorts to be,” Murphy contends. “The best way to honor and celebrate Fredo’s life and contribution to rap is to endorse what he truly represented—entrepreneurship. He would want to see the doors open for not just rappers but particularly Black rappers from the hood who make Drill music. He would want to see not just performance opportunities for Drill rappers, but business opportunities so they can help better the hood and their people.” In contrast with cities like Atlanta, where hip-hop and politics are closely intertwined, Chicago has held its creative pioneers at arms’ length.
Fredo’s death was tragic, and it shouldn’t have happened to someone so young. Yet while his life was shaped by tragedy, it was not defined by it. His impact on the world was also not limited by his significance as a recording artist; while he played an important role and his work is worth exploring, in Fredo’s case, his personality exceeded his artistic limitations. To those who loved him, he telegraphed humanity and comfort. “It was good to be able to hug you,” Keef posted to Instagram the day after his cousin passed.
In conversation, DJ Kenn recalled a memory from 2012, when Fredo was still new to his own celebrity. Kenn had just finished shooting the video for Fredo and Gino Marley’s “My Plug” with the two rappers in a location at 61st and Indiana. As they left the building, they were swarmed by people from the neighborhood. “The people came up like, ‘Fredo is here!’ Everybody was there,” he told me. “He had a few hundred in cash [on him], it may not have been much, but he started giving money to the people. He gave everything away, $5, $10, trying to help people, help the streets a little bit. He was a really stand-up dude. He was not really selfish. I know he really helped a lot of people. More than just music, put money in their pocket.”
David Drake is a writer based in Chicago. Follow him on Twitter.
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