Fredo Santana in fall 2017 Credit: Courtesy of Fredo Santana's Instagram

Few lyrics are as emblematic of drill as “Fredo in the cut / That’s a scary sight,” from Chief Keef’s 2012 breakout hit “I Don’t Like.” Guest rapper Lil Reese delivers the blunt, menacing lines with a hint of playfulness—and all those characteristics apply to the man they’re about. “Fredo” is Chicago rapper Fredo Santana, born Derrick Coleman. He’s there in the “I Don’t Like” video, bouncing around an apartment shirtless along with most of the rest of Keef’s GBE crew. But Fredo hardly blends in: he shoots the camera a quick glower that can send shivers down your spine, and the cross tattoo between his eyebrows makes an instant impression. “Fredo stood out to me,” 50 Cent wrote in a memorial Instagram post on Sunday. “When he said he looked up to me, l wanted to work with him but we didn’t get the chance to do anything.”

Fredo died Friday in Los Angeles at age 27. Chicago Tribune editor Kevin Williams wrote on Saturday that the LA County medical examiner’s office had confirmed the death. TMZ reported the same day that Fredo died as the result of a seizure. Speculation has run rampant online that Fredo’s death was linked to his addiction to lean; he’d vowed to kick the cough-syrup habit after he was hospitalized for liver and kidney failure in October.

It’s hard to look back on drill’s rapid ascent in 2012 without seeing Fredo’s influence and persona everywhere. Drill became a phenomenon in part because so many local rappers emerged with their own subtle twists on it; Keef lit the match, but Fredo joined the crowd pouring kerosene on the fire. And as a member of GBE—and as Keef’s cousin—he was at the center of a nexus of talented rappers. Fredo was five years older than Keef, and he put out his first mixtape, 2012’s It’s a Scary Site, at the relatively advanced age of 22. He understood the value of cultivating a public persona, and he leaned into his villainous image—even rap fans who couldn’t name a single Fredo song knew he wasn’t someone to mess with.

Fredo went on to release eight more mixtapes and one studio album, 2013’s Trappin’ Ain’t Dead, which features a verse from Kendrick Lamar that’s been remarked upon widely since Fredo’s death. It’s especially impressive that Fredo got Kendrick to appear on a self-released album after he’d made his own major-label debut with Good Kid, M.A.A.D. City. Occasionally rappers guest on each other’s songs because they share a label, but that wasn’t usually the case with Fredo—he put out his mixtapes and his album through his own Savage Squad Records. (He posted a video on Instagram in November announcing he’d signed Keef.)

Looking at Fredo’s catalog, it’s easy to see how many other rappers respected him. Chicago all-stars filled his mixtapes, of course (Keef, G Herbo, King Louie), but Fredo also pulled in verses from Atlanta royals Future and Gucci Mane (on 2013’s Fredo Kruger and 2015’s Ain’t No Money Like Trap Money Vol. 1, respectively), New York Diplomat Juelz Santana (Fredo Kruger), genre-blending Renaissance man Childish Gambino (2014’s Walking Legend), Baton Rouge veteran Kevin Gates (Ain’t No Money Like Trap Money Vol. 1), and Houston underground legend Z-Ro (2016’s Fredo Mafia), to name a few. As the rest of the pop world backed away from drill after 2012, rap continued to embrace Fredo. In 2013 Drake cast him as a villain in the video for “Hold On, We’re Going Home,” the biggest hit from Nothing Was the Same.

Fredo could handle the volatile threat built into the drill sound as though it were a toy—he was the kind of instigator who’d hold on to a lit bottle rocket just long enough to freak everybody out, and love every second of it. On “Kill U on Camera,” from September’s Fredo Kruger 2, he raps so slowly that he seems to be savoring every syllable, but even as he talks about gunning you down he keeps a light touch. Fredo was a dependable rapper, one who didn’t bullshit around—he was so committed to his persona that it was hard not to buy into everything he said. He knew how to use fear to his advantage, and it made him look invincible. That’s part of what makes his death hard for me to take—I never saw it coming.