Fredo Santana’s Honest Rhymes Fueled Chicago’s Drill Movement and Influenced a Generation

Meaghan Garvey
·6 min read
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When the video for Chief Keef’s mainstream breakthough, “I Don’t Like,” hit the Internet in March 2012, you paid attention. The budget couldn’t have been more than a few hundred dollars, shot spontaneously in a living room while 16-year-old Keef was on house arrest: here were a dozen or so shirtless young Chicagoans, turning up to the hottest song most of the city didn’t know about — yet.

For some viewers the appeal was danger, a vicarious first-person peek into a part of Chicago’s South Side generally only seen through concern-trolling news clips. And for others, the appeal was representation — an opportunity denied, pre-YouTube, to those who saw themselves and their friends in that living room mosh pit. In the middle of it all was a guy with an upside-down cross tattooed right in the center of his intense glare. It made sense when you realized he was the Fredo Santana — as in, “Fredo in the cut, that’s a scary sight!” Of all the catchy one-liners from “I Don’t Like,” that seemed to ring through Chicago the loudest that year; it even got its own T-shirt. Keef was the drill movement’s brightest star, but Santana was drill incarnate.

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Born Derrick Coleman in 1990, Santana was Keef’s cousin. He was the oldest member of GBE (Glory Boyz Entertainment, later known as Glo Gang) and though its members were peers, it was clear that Santana served as a de facto mentor figure, too. Born in Parkway Gardens — specifically “O Block,” an area designated as Chicago’s most dangerous block in terms of shootings between 2011 and 2014 — Santana grew up quickly. He studied the way poverty ravaged his family, his neighbors, the black community around him. And though he’d been serving time for a probation violation during the first few months of Keef’s rise, by the time he was released in February 2012, he immediately began grooming himself into a serious rapper.

Santana took note, too, of how the media treated Keef when he’d grant the rare interview; instead of listening to the teenager, reporters more often sounded like they were trying to exploit him — folding the rapper into their Chicago gun violence narrative rather than seeing it through his eyes. And so the reputation with which Santana was saddled early on — straight-up scary, as advertised — was a defense mechanism against misunderstanding, as well as a response to repressed trauma. Clearly he was not one to be played with, but he had fun with the villain character, too; when Drake personally requested him to make a scene-stealing cameo in the video for “Hold On, We’re Going Home,” Santana freestyled the role of the bad guy with a wink.

The roughness of early drill wasn’t a design flaw, but the whole point, and one of the best full-length examples of it was Santana’s debut mixtape, September 2012’s Scary Site. Back then, many onlookers assumed that drill didn’t have the range to sustain itself for too long. But on Scary Site, Santana’s staccato snarls on the war-ready “My Lil Niggaz” sat alongside the baroque arpeggios of self-reliance anthem “Got Myself” and the triumphant proto-bop number, “Glory Shit.” And though it originally appeared on Lil Reese’s Don’t Like tape earlier that year, tape closer “Beef” (which features Santana and Reese, along with Lil Durk) remains one of the best songs to come from the drill movement, period — a Young Chop-produced masterwork of controlled chaos.

Casual listeners’ focus had drifted post-Finally Rich, as had the major label co-signs; but Santana, forever a student of the game, was only getting better. His gruff delivery had grown impressively dynamic, his storytelling more vivid. On “Jealous,” a cut from his sole studio album, 2013’s Trappin Ain’t Dead, Santana more than held his own alongside Kendrick Lamar, easily drill’s highest-profile guest appearance since Kanye remixed “I Don’t Like.” (Perhaps even more impressive: Lamar name-dropping Chicago landmark Harold’s Chicken on the track.) And though Santana’s numerous projects were never without blood-thirsty battle cries, from 2013’s “Rob My Plug”  to last year’s massive Glo Gang posse cut “Go Live,” it would be a mistake to reduce his artistic legacy to just the savage stuff.

When asked, in a 2013 interview, what his early music sounded like, his response was decisive: “It sounds like struggle. I don’t rap too much about flashy type stuff, you know… I rap about struggle, heart, life in Chicago.” He didn’t need to spell it out, though: the music spoke for itself. On 2014’s heart-wrenching “Half Of It,” a lifetime of pain bleeds through Santana’s Auto-Tuned bars: “I remember sleeping crib to crib, broke with no clothes/ They don’t know the half,” goes the hook.

Much ink has been spilled over rappers’ often-fatal dependence on lean; this epidemic is by no means a recent phenomenon, but that doesn’t soften any one blow. And so when word spread, late Friday night into Saturday morning (Jan. 20), that Santana had been found dead in his Los Angeles home, having suffered a seizure from what appears to be kidney and liver failure, a familiar strain of thought echoed across social media, imploring addicts to quit the lean ASAP. It’s certainly sound advice. But at the same time, these anti-drug platitudes gloss over what may have attracted someone like Santana to such notoriously high-risk narcotics in the first place — in his case, a lifetime of trauma, and a resulting case of untreated PTSD.

What makes Santana’s death especially painful is that, over the last year, he had not only acknowledged this often-stigmatized reality, but used himself as a beacon to others who might also be turning to drugs to self-treat serious mental health issues. After being hospitalized last October after years of lean dependency, Santana opened up about his situation on social media: “Hopefully I can be the face to sho niggas to slow down an we got our whole life ahead of us f— being rock stars gettin high I got PTSD,” he tweeted. Since then, Santana had been sober; last June, he and his girlfriend had welcomed the birth of their first child, a boy.

Santana’s legacy as a rapper might not be as frequently acknowledged as Keef’s, but he’s no less essential to one of the most influential and truly groundbreaking movements in 21st century hip-hop. That influence extends well beyond his hometown of Chicago. There’s a whole generation of young rappers raised on Santana; without him, there is no 21 Savage, no Lil Uzi Vert, no Playboi Carti, his influence evident from the delivery to the lingo to the face tattoos.

Listen to last September’s Fredo Kruger 2 tape, his final release: “Off the Meter” in particular feels like a blueprint for trap’s new wave. Outside of his musical legacy, though, perhaps the most important thing Santana leaves us with is a reminder — as music fans, and as human beings—that our best tool for understanding art is empathy.

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