Drakeo the Ruler, who helped define the sound of L.A. hip-hop, dead at 28 in stabbing

Drakeo the Ruler, whose surrealist slang made him one of the most original stylists in L.A. hip-hop, died Sunday morning from injuries after a stabbing at the Once Upon a Time in L.A festival. He was 28.

His attorney John Hamasaki said in a statement, “We spent the hardest two years together fighting for his freedom, facing life, before walking out a free man just over a year ago. Through it, we became friends and then like family. I don’t even know how to start processing this.”

The rapper, born Darrell Caldwell, was raised in South L.A. and attended Washington High in the Westmont neighborhood. He quickly developed an idiosyncratic but evocative palette of lyrics.

“I know how to code everything and I switch it up every time I get bored,” he told The Times in 2018. “People think I just make up words, but everything means something.”

After being discovered by local hip-hop production hero DJ Mustard, Drakeo helped define the region’s rap sound in the wake of imaginative, challenging superstar acts of the 2010s like Tyler, the Creator and Kendrick Lamar.

Hip-hop artist Drakeo the Ruler outside a recording studio in Los Angeles in March.

(Wyatt Winfrey)

Drakeo recorded several popular and acclaimed mixtapes, including 2018’s “Cold Devil” and 2020’s “Thank You For Using GTL.”

But his rap success arrived at a difficult time in his young life. Until last year, he was on trial in connection with the killing of a 24-year-old man in 2016.

He recorded his vocals for “Thank You For Using GTL” via telephone while at Men’s Central Jail in L.A.

After he was acquitted of felony murder and attempted murder charges, county prosecutors sought to retry Drakeo on conspiracy charges related to the slaying. Caldwell ultimately accepted a plea deal and was released in November 2020.

“I live a nervous life. I gotta look around and watch my back from police and these other [people] out here,” he told the Times in 2018. “[People] want to kill me. I can’t be driving around in $100,000 cars on the run, listening to soft-ass [music].”

Drakeo the Ruler performs in 2017.

(Dewanne Buckmire)

Drakeo released his most recent studio album, “The Truth Hurts,” in February, with cameos from superstar Drake and Don Toliver. His most recent mixtape, “So Cold I Do Em 2″ came out Dec. 7.

The L.A. Fire Department responded to a call at 8:40 p.m. about an altercation at the Once Upon a Time in L.A. festival, held at t Banc of California Stadium in Exposition Park. A source who was not authorized to speak publicly identified the victim as Drakeo. The festival’s remaining sets, which were to feature the Isley Brothers, YG, Snoop Dogg and 50 Cent, were canceled.

In a statement Sunday morning, Snoop Dogg — a co-promoter of the festival with Live Nation — wrote on social media that he’s “saddened by the events that took place last night at the Once Upon a Time in L.A. festival…Last night I was in my dressing room when I was informed about the incident and chose to immediately leave the festival grounds. My prayers go out to everyone affected by the tragedy. Please take care, love one another and stay safe y’all. I’m praying for peace in hip-hop.”

Caldwell is survived by his son and brother, the L.A. rapper Ralfy the Plug.

This story is developing.