Drakeo the Ruler spoke in his own language — and the world listened

The Los Angeles rapper suffered a gruesome death, but survived bogus charges and left a powerful legacy.

SAN BERNARDINO, CALIFORNIA - DECEMBER 12: Drakeo the Ruler performs at 2021 Rolling Loud Los Angeles...
Timothy Norris/WireImage/Getty Images
ByJayson Buford

Drakeo the Ruler didn’t just rap; he slithered over a beat. The Los Angeles rapper had a quiet cadence, stalking his prey with assonance and lingo that only he and a select few understood, making it all the more impressionable and menacing when you heard him. He coined his craft as “nervous music” for his herky jerky flow and how uncomfortable he sounded while rapping. He was minimal, but intricate and primal, with a flow that ran counterclockwise to the beat. He delivered his lyrics with a mumble, almost as if he was rapping to himself, but the whole world heard him — he amassed a following that started in Los Angeles and ballooned to millions of streams worldwide, and other rappers began to copy his style as well.

Saturday night in Los Angeles at the Once Upon a Time in LA' festival, Drakeo the Ruler (born Darrell Caldwell) was fatally stabbed in the neck shortly before going on stage for his performance. He was a devoted father, a loving son, and a protective brother — and hailed by critics as the “most original West Coast stylist in decades,” But aside from the rap world’s major loss of such a one-of-a-kind talent, the violent end feels even more tragic when you consider what Drakeo had to overcome to become a free man.

Drakeo the Ruler was a victim of the state’s carceral system and racist investigations throughout his life and career. In March 2018, after releasing the acerbic Cold Devil to critical acclaim, the Los Angeles County Sheriff’s Department arrested Drakeo and several other members of his Stinc Team crew for murder and attempted murder dating back to a shooting in Carson, California in December 2016. If it seemed like the entire subset of rap fandom was railing against the prosecution, it was for good reason. The evidence was always flimsy, and outright exploitative: the prosecution claimed that Drakeo, engaging in a rap beef with RJMrLA, caused a shooting to break out. They used examples from songs he had made dissing RJ, making it seem like music provided the motive for taking a human life. (This practice has also been levied against other rappers in recent years, such as Tay-K and YNW Melly; the former has been convicted of murder and awaits trial for a second murder charge, while the latter awaits a double murder charge that begins in March.) After being acquitted, he was locked up again on criminal gang conspiracy — a charge that was first implemented for high ranking American Mafia members, not for South Central Los Angeles rappers and rap groups. Here is where Drakeo became a political prisoner, held captive and persecuted for music - with the District Attorney’s office claiming that the Stinc Team was not a rap group - but a gang.

While awaiting trial at Los Angeles Men’s Central Jail, Drakeo and producer JoogSZN dropped the excellent, ironically titled Thank You for Using GTL, an album recorded from jail. As a gangster rapper, you’re surveilled and presumed guilty before the judge can even set bail on you, or in Drakeo’s case, remand you back to Men’s Central. A voice on the phone line stated, “This call is being recorded,” followed by Drakeo unleashing some of the most tightly-wound raps of his career. A crowning achievement in technical musicianship and audaciousness from both Drakeo and Joog, he stops and proclaims his innocence and the power of his art on the final track, “Fictional.” “This might sound real but it’s fictional,” he insists. “I love that my imagination gets to you.” After Jackie Lacey — the Los Angeles DA whose office was trying Drakeo — lost the election in November 2020, a plea agreement was reached and Drakeo was allowed to come home. In February 2021, “Pow Right in the Kisser,” off of The Truth Hurts, was one of the best songs of the year, with Drakeo and the Stinc Team upping the ante every bar. It’s as if they were saying, This is our artform. You can’t stop us. The same lyrics that detectives used to paint him as a criminal were now making him a rap superstar. A Drake feature came and everyone knew what the hierarchy was in Los Angeles.

Whether before prison and in the short 13 months of freedom he had before his untimely death, Drakeo The Ruler brought distinctive slang, mannerisms, and flows that were enjoyed and imitated, yet too unique to truly duplicate. Like Ghostface Killah, he had the power of raw charisma and words that only made sense within his own cosmology. “Flu Flamming,” a brilliant ode to home invasions over sparse, ominous production, exemplifies this. The album was uniformly excellent (especially the 03 Greedo-featured “Out the Slums,” one of the best collaborations of the last half-decade), but "Flu Flamming" is the song I’d show to traditionalists who didn’t know what to think of his flow. His idiolect was undecipherable unless you’re in the know, but he delivered terms like "chopsticks" (automatic weapons), “mud walkin’,” (walking around under the influence of lean), and “flu flamming” (home invading) with a knowing, shadowy smirk. And if you missed those references, he still had crystal clear bars that hit you between the eyes: "I’m Luke Skywalker with this Glock playing laser tag."

Drakeo the Ruler deserved better than what happened to him Saturday night. Being a rap artist is a job, and no one should be unsafe at work. This is a crime that is hard to process. Yes, rappers have died of violent crimes before, and rap music is getting increasingly and alarmingly more voyeuristic with its hunger to see crimes in real time. But to hear Drakeo rap was to hear someone changing the rules in real time. At the time Cold Devil came out in 2017, rap was in the midst of an era full of sing-along anthems about downing drugs and scorned lovers, and Los Angeles being ruled by Kendrick Lamar and ScHoolboy Q’s John Singleton-like narratives and Odd Future’s church-burning chords. Drakeo upended that with lyrics that took your head off and colloquialisms that needed an entire league of fans to unfilter. When he first burst onto the scene he didn’t have narratives within his music. He didn’t title his albums based on artsy motifs like To Pimp a Butterfly. The state of California simply gave Drakeo the narratives he needed to be a folk hero, and he was as great a rapper as any in recent years.

To put Drakeo in the same category of Tay-K means that you think he is guilty and a violent criminal. Whether in the courtroom for his two trials or in the audience on the night of his murder, Drakeo deserved better than what the world gave him. Yet, his art was powerful as a result of the juvenile homes, the sadistic Los Angeles police force, and the street clashes he got into. Rap music, like any other artform, bleeds into real-life. But it doesn’t mean that the rappers who make music are all violent criminals. Nor does it mean that we shouldn’t begin to wonder what we can do to help young rappers navigate their way in the world.