Issue 16 of Highsnobiety Magazine features a cover story with the brand FTP. The chosen image was one from their archives of the late Fredo Santana, the beloved rapper who unexpectedly passed away in January. We thought it appropriate to highlight Santana and his legacy with this standalone piece. In addition, proceeds of this issue of the magazine will be donated to his baby son, Legend Derrick Coleman.

There’s something heartbreaking about seeing talented artists cut down in their prime. Whether it’s the untimely passing of Amy Winehouse, Lil Peep, or Avicii, it leaves a hole in our collective cultural consciousness, one that comes with an extra layer of added tragedy in their perceived unfulfilled potential. In January 2018, Chicago rapper Fredo Santana (real name Derrick Coleman) departed this mortal coil and joined the ranks of the ill-fated 27 club. Santana left a lot behind: his girlfriend and their eight-month-old son, Legend Derrick Coleman, a recently started weed business in California, his own label, Savage Squad Records, as well as a music legacy that is only now beginning to come into focus.

Coming up alongside his younger cousin, Chief Keef, Santana was a key player in the development of drill - an offshoot of trap that blew up in 2012. He helped to elevate it from the local Chicago hip-hop scene to a worldwide phenomenon (its British counterpart, UK drill, has recently been making headlines).

Born on the 4th of July 1990, Santana grew up in the "O Block" of Parkways Gardens (as referenced on Santana tracks like “My Lil N*ggas”), a South Side, low-income housing complex that sits on 62nd and King Drive in the neighborhood of Englewood. “I wasn’t a rapper at first. I was just a street n*gga that was just rapping on the block, not going into the studio,” Santana told Noisey in 2013. “We was already famous in Chicago… Everybody knew me from everywhere. Even opposite gang members, all around. I’ve been sellin’ drugs since 12 years old.”

The first taste most people outside of Chicago had of Santana was a name check from Lil Reese on Chief Keef’s blow up track “I Don’t Like," followed by Santana’s appearance in the track’s video (shot in Keef’s living room while he was on house arrest).

Santana’s presence - and trademark upside-down cross forehead tattoo - stole the limelight and left viewers wondering just who the hell that guy was. Later, Drake would recruit Santana for his own music video “Hold On, We’re Going Home," which saw Santana play a bad dude who kidnaps Drake’s girlfriend.

The way Santana collaborator DJ Kenn tells it, witnessing Keef’s success was what got Santana into the studio: “They'd never write, they'd only do freestyles,” he said, “But once Keef started to go crazy, people find out, and realize this shit's gonna happen if we take it seriously.”

Fredo Santana delivered his debut mixtape, It's a Scary Site, in 2012, featuring production by TM88, Young Chop, 12Hunna, Leek E Leek, j-Hill, C-Sick and Paris Bueller, as well as boasting appearances by his Chicago rap peers King L, Gino Marley, Lil Herb, Lil Durk, Lil Reese and, of course, Chief Keef. Santana’s second tape, Fredo Kruger, arrived in 2013, cementing his affiliation with horror-movie aesthetics and upping Santana’s game with 808 Mafia, Young Chop and Mike WiLL Made It on production duties. That same year saw the release of Santana’s lone studio album, the self-released Trappin Ain't Dead, which featured Pulitzer Prize-winner Kendrick Lamar on the track "Jealous."

The barrage of artists featured on Santana’s own work - whether it’s Kendrick, Migos, Juelz Santana, Soulja Boy, Young Scooter, Fat Trel, or PeeWee Longway - are cosigns that speak volumes about Santana’s own talent. His real deal street credentials, coupled with his autobiographical lyrics reflecting the poverty and violence that surrounded him growing up, made him an authentic voice in rap, shaping his career and earning him respect in the process. As he told Noisey in 2013, “I don’t rap too much about flashy type stuff, you know...I rap about struggle, heart, life in Chicago.”

Santana’s flow wasn’t sugar-coated; it was brutal, because at times his life was brutal - a reality that resulted in seeing friends gunned down and in serving actual jail time. Despite fully committing to and exploiting a persona that included horror movie-referencing artwork, violent lyrics, and a penchant for the devil emoji, Santana was no cartoon villain. Instead, he made use of his limited range to the fullest and, rather than glamorizing his past, he told stories that infused dread and honesty into harsh realities.

For example, Santana directly addressed his past drug use in a tweet responding to a picture of the rapper Russ wearing a T-shirt emblazoned with an anti-lean/anti-xan message. “How Much Xans and Lean Do You Have To Do Before You Realize You’re A Fucking Loser,” the T-shirt read, to which Santana bluntly replied “Until I can stop thinking bout my dead homies an the trauma that I been thru in my life that’s when I’ll stop.”

Fredo Santana’s journey from hustling street kid to successful rapper follows in the tradition of rappers like JAY-Z and 50 Cent and is a story as old as the rap game itself (along with the moral panic it fuels in those that do not understand it). In one way, Santana’s story is symptomatic of America and its systemic and endemic prejudice against African-American men, something that’s evident when you look at the latest Federal Bureau of Prisons statistics which show that approximately 13% of the American population is African-American but they make up a disproportionate 37% of all inmates.

On the flip side, Santana’s story is the embodiment of the American Dream, someone who came from nothing with the odds stacked against them, who worked hard and achieved success, fame, and money; as Santana says himself on "Came Up From Nothing," he “turned nothing into something.”

At the time of his death, following a seizure linked to health issues relating to drug use, Santana had given up lean and been 60 days clean. “I was running from my old life tryna get high didn’t want to face them demons... I’m getting help I might just go to rehab,” he’d tweeted after previously being hospitalized for liver and kidney failure, “Hopefully I can be the face to sho n***as to slow down an we got our whole life ahead of us fuk being rock stars gettin high I got ptsd [sic]." Ultimately, Santana couldn’t outrun his troubled and traumatic past, but - as with the death of Lil Peep - Santana’s untimely passing has sparked much-needed conversations about the very real complexities of drug use, addiction, self-medicating and mental health.

Those conversations began almost immediately after Santana’s passing, with Lil Durk declaring it “fucked the whole city up,” and D-Savage describing Santana as a “mentor” and someone who “just wanted to see the next person do better.” DJ Mustard reacted by posting a video of himself pouring a bottle of lean down the sink. "It's over for me, people," Mustard says in the clip, "It's over. Fuck this shit. I'm cool. Fuck that, it's over."

While Vic Mensa directly addressed Santana’s trauma, “He spoke about his drug use and trying to escape the PTSD he had from growing up in the hood, surrounded by violence,” he went on to say, “I call it post traumatic streets disorder. We need to evaluate the conditions in our communities that raise young black men with more psychological issues than they can ever really unpack. We have to diagnose the system, not the symptoms.” But perhaps Santana put it best himself when he rapped, “They don't know my struggle, they don't feel my pain.”

In retrospect, it is not only easy but necessary to find closure in giving Fredo Santana’s life and death a narrative that, at least in some ways, makes sense of and gives meaning to his passing. Like the renegade Nexus-6 Replicant Roy in Ridley Scott’s Blade Runner, sometimes the light that burns twice as bright burns half as long. Rest in power Fredo Santana.

Pick up Highsnobiety Magazine Issue 16 to learn more about FTP and why they chose to highlight Fredo Santana in our cover soot.

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