The Ruler’s Back: Drakeo the Ruler Is Finally Free—and Ready to Talk

Editor’s note: This story was updated on Friday, November 13, at 5:45 p.m. ET with comments from Deputy District Attorney Phil Stirling.

On November 2, Jackie Lacey had yet to be voted out as Los Angeles County district attorney, and Drakeo the Ruler still languished in solitary confinement in downtown Men’s Central Jail, staring down the abyss of 25 to life. As the nation fixated on the looming election, the South L.A. rapper’s retrial quietly began in the ghostly Compton Courthouse. Facing charges of criminal gang conspiracy and shooting from a motor vehicle, Drakeo and his defense team prepared for scorched-earth combat that would last into the new year. But in a startling twist just 48 hours later, the most original stylist on the West Coast accepted a plea deal to gain his release following nearly three years of incarceration. By that Wednesday night, Drakeo was free and Lacey was a lame duck.

The case traces back to Davion Gregory’s killing at a Carson adult pajama party in December 2016. The 24-year-old was shot five times as he was about to enter the party; he was pronounced dead on arrival at Harbor-UCLA Medical Center. Drakeo’s childhood friend and codefendant, Mikell Buchanan, would eventually be convicted of first-degree murder for firing from the back seat of Drakeo’s recently purchased Mercedes SUV while Drakeo sat in the parked vehicle’s driver seat. Prosecutors alleged that Drakeo had armed members of his “criminal street gang” as part of a plot to kill a rival rapper named RJ (who neither attended the party nor was scheduled to appear).

According to the prosecutors’ argument, because Drakeo had planned to kill RJ and had armed the group for that purpose, Drakeo was responsible for and therefore guilty of all violent crimes committed that evening. The “gang” in question was the Stinc Team, Drakeo’s rap crew, which Drakeo, his defense team, and expert witnesses have insisted throughout the proceedings are not a gang, despite the DA’s classification. They’ve also denied any intent to kill RJ, who has since defended Drakeo in various media appearances. Throughout that first trial, which began in May 2019, the prosecution weaponized Drakeo’s own lyrics and videos against him, showing jurors endless loops of him rapping while clutching semiautomatic rifles.

Born Darrell Caldwell, Drakeo was first acquitted in July 2019 of a barrage of charges: first-degree murder, attempted murder, and conspiracy to commit murder, while being found guilty on one gun-possession charge stemming from an unrelated police stop. In September 2019, Lacey’s office opted to refile the two remaining counts that the original jury hung on: shooting from a motor vehicle and 182.5 in the California penal code, a criminal gang conspiracy law that claims that a member of a gang can be guilty for another gang member’s crimes if they promote or stand to benefit from them. (In a statement provided to The Ringer on Friday, Deputy District Attorney Phil Stirling said that retrying those charges “was not a political decision or a decision based upon anything close to vengeance.” “The defendant was reasonably believed to be legally and morally responsible, in part, for the Gregory murder,” he wrote.)

For most of the last year, Drakeo was formally silenced with a gag order, prohibiting him from publicly discussing the facts of his case or inasmuch as tweeting “Free Drakeo.” Flouting the sanctions, Drakeo continued to tweet regularly, conduct interviews, and record the best album ever rapped over a jail phone, this summer’s critically revered Thank You for Using GTL—a sly, brilliant missive against these tortures and a testament to rap as a hyper-imaginative branch of Black art.

As November began, the proceedings for what would’ve been his second trial in connection to Gregory’s killing commenced with a Roman brutality. Over the course of seven hours, Drakeo’s attorneys John Hamasaki and Kellen Davis moved to disqualify the district attorney’s office from prosecuting the case because of what the defense described as massive conflicts of interest. They cited the $1.3 million that the sheriff’s department had funneled to Lacey’s reelection campaign; the prosecution’s failure to disclose at the first trial that one of the lead investigators, Deputy Sheriff Francis Hardiman, was married to a high-ranking member of Lacey’s office; and the perceived bias of the judge, Laura Walton, a former prosecutor and colleague of both Lacey and the deputy district attorneys trying Drakeo’s case. In particular, Hamasaki and Davis referenced everything from Walton’s decision to slap Drakeo with a gag order to an impromptu lecture at the first trial in which she appeared to hint that Drakeo should fire Hamasaki in favor of his original attorney, Frank Duncan. In the idealized version of the criminal justice system, judges, law enforcement, and the district attorney’s office are three distinct entities; here, they appeared to work hand in glove. (The L.A. County Sheriff’s Department declined to comment for this article.)

Since Drakeo was first indicted in connection to the Gregory killing in March 2018, Jackie Lacey’s office has presented a dizzying labyrinth of charges against him and the Stinc Team, jailing or incarcerating nearly every member of the crew for everything from murder to credit card fraud, spray-painting graffiti and holding guns in music videos, witness intimidation, and burglary. During Drakeo’s first trial, the prosecution even trotted out representatives from the state’s tax board to levy accusations of tax evasion. While nearly all of Drakeo’s peers were offered deals (which most took), at no point did Lacey’s office broach the topic with Drakeo’s legal team. So it was particularly shocking when prosecutors dangled the prospect of a plea bargain before the defense after the November 2 court session.

A day of tense negotiations followed. On November 4, Drakeo agreed to plead guilty to the crime of shooting from a motor vehicle with a gang enhancement, which meant acknowledging in a court of law that the Stinc Team is a gang. (In his statement, Stirling said that the D.A.’s office extended the plea deal in part to avoid a lengthy trial during a pandemic and that “the victim’s family was satisfied with the disposition.”) Outside of the courtroom, Drakeo continues to vehemently proclaim his innocence and lack of gang affiliation, but faced with the chance to obtain his immediate freedom after being locked up for several years, he took the prosecution’s deal. As part of the bargain, the district attorney’s office and judge promised to release him from jail in exchange for time served. The conditions of his parole will last five years, and any minor violation could lock him up again for nearly a decade.

The plea brings resolution to one of the more high-profile cases of Lacey’s eight-year tenure—which criminal justice advocates have watched closely. Lacey lost the November 3 election to progressive prosecutor George Gascón, who has vowed to move the office away from its “tough on crime” past and toward more humane reforms. In his first meeting as district attorney–elect on November 9, Gascón spoke with victims of police violence at a forum organized by Black Lives Matter–Los Angeles. He has publicly vowed to stop the use of the death penalty and gang enhancements, approaches that Lacey regularly pursued and that proved central to Drakeo’s case.

Upon his release, the self-anointed Mr. Get Dough immediately changed into a Gucci turtleneck at a nearby IHOP, threw on a pair of blinding and bespoke diamond chains, and hit the bank to withdraw the maximum amount of cash allowed ($20,000). In the hours after leaving custody, the independent street-rap phenomenon was besieged by million-dollar label offers and well-wishes from Roddy Ricch and Rich the Kid. Gucci Mane, Lil Baby, and Lil Yachty joined to watch him address his fans on Instagram Live. At one point on November 4, Drakeo was the only national Twitter trending topic unrelated to the presidential election.

Armed with a stack of lyrics for over 200 songs scrawled on loose-leaf paper that he wrote while jailed in a place the ACLU has called a modern-day medieval dungeon, Drakeo headed to the studio to begin recording We Know the Truth, the full-length project that he plans to drop soon. The video for the first song laid down, “Fights Don’t Matter,” immediately trended on YouTube following its release late Sunday night, eclipsing 200,000 views in the first 24 hours. It may have been written while in MCJ, but it’s classic Drakeo, summoning an opiated vortex of cryptic slang, beatdowns with Neiman Marcus merchandise, Paisa dances with the plug, and Jet Li kicks that get blood on his Boosie fade. Unlike the early videos that first brought him fame, neither Drakeo nor his crew tote arms in “Fights Don’t Matter.” That’s a stipulation of his parole, but also an indication of how seriously he’s taking this second chance. While it doesn’t reference the circumstances of his travails, the hook (“Ima give him 33 shots, cuz fights don’t matter”) aims at his rivals, legal or otherwise, who might have hoped for a more pacifist comeback.

I first met the 26-year-old from South L.A.’s Westmont neighborhood in 2017 at the Men’s Central Jail, where he was then incarcerated for illegal possession of firearms by a felon. (Sheriff’s detectives raided Drakeo’s apartment in January 2017, searching for the guns used in the Gregory murder. They didn’t find them, but locked him up for possessing rifles that had been frequently brandished in his videos.) In the past three years, I’ve followed his case closely, spending countless hours on the phone with him from jail, hoping for his release from the traps of a system that seemed to be railroading him, but unsure when or if that day would ever come.

It’s myopic to say that this is a new Drakeo, because he steadfastly refuses to let the events of the past three years dictate his lyrical focus or artistic impulses. He will always remain the person who made “Fuck Being Humble.” Yet there is a deeper understanding of the consequences of his choices, a realization of life’s gravity, and how swiftly everything that he’s worked for can be snatched away. Shortly before he filmed the video for “Fights Don’t Matter,” we sat down at a Burbank studio for his first interview since regaining his freedom. In a nearly hour-long conversation, the pioneer of the sinister “nervous music” subgenre discussed the surreal nature of his sudden release, the tribulations endured, and his plans for world domination.

This interview has been lightly edited for length and clarity.

What’s gone through your mind since you’ve been released?

All I’ve been thinking about is if I’m going to go back to jail. I don’t know if that’s weird, because the DA and sheriffs fucked my head up so much that I have to watch my back about everything that’s going on.

You’ve spent 34 months in Men’s Central Jail. For almost the entirety of the last year, you’ve been in solitary confinement. What was the impact of that on you?

It was definitely torture. It fucks with your head. I still can’t go places right now without looking over my shoulder, or turning my head every time the door opens.

It makes you more [inclined to be] violent. You could be the calmest, coolest person in the world, but being in there, you change. Things that would be little on the streets become the most serious thing. The cell seems to get smaller and smaller. There’s only so much you can put in there. It’s not the same size bed as a regular bed; the mattress hangs off the bed, so you have to sleep toward the wall. You have to work out diagonally, and still somehow, you hit the toilet.

You were in solitary all summer as the coronavirus spiked and caused the corrections officers to enact even stricter lockdowns. Did that compound the misery?

If you did have visits, they took [away] the visits. You can’t talk to your family because most people can only use the phone to contact their attorney; there’s no visiting, they don’t clean, it’s dirty as shit. It’s crazy and it just fucks with your head.

So on November 3, you just watched the results of the election from jail, waiting to see how the rest of your life would shake out the next morning?

Being in jail, we don’t really give a fuck about the presidential election. That shit is not really going to change nothing; all it’s going to do is promise people, “We’re going to do this,” and then they’ll block it. Everybody watched all that shit, but nobody was worried about it. Everybody was really worried about the DA election.

You were the only one charged in connection to the Gregory case who wasn’t offered a deal until now.

The only one. And I’m the only one that had a criminal gang conspiracy charge. I wasn’t a gang member; I’m still not a gang member, but hey …

I’m a prime example of what happens to 90 percent of Black people in the system. I was acquitted of damn near every single charge, and I still had to plead to a gang enhancement to go home. I’ve been here for three years, fighting the death penalty, fighting life without parole, and even I cracked and took a gang enhancement. They wanted to make that clear that I had to do that to come home. [Ed. note: Before his first trial, prosecutors indicated in court that they would seek the death penalty, but they decided against it.]

How did you find out about the possibility of receiving a deal?

I was talking to [my producer] Joog[SZN] on the phone for a minute, clowning around like we always do, and then he’s like, “John [Hamasaki] wants you to give him a call.” I called John and he was like, “Don’t get too happy or overthink this, but the DA came and they want to resolve things.”

At first, it was like, “Nah, I don’t trust these people, it has to be something else.” After all the stuff they’ve put me through, I doubted that they’d give me a deal. I was like, “Nah, they’re doing this to get [John] off our game, and then we’ll go to court and they’d be like, “A deal? Nah. You’re going to trial.” Then I went into court on Wednesday and …

Were you able to sleep the night before?

I tried to for like two hours. Then I woke up and threw up for a long time. I thought I was going to die.

How difficult was it to take a plea for something that you didn’t do?

Oh boy, I did not want to take that plea. I still feel like it’s a setup; they want me to get into trouble. They feel like this is a win for them. I still had to plead out; they still got the gang enhancement. I still have the same judge, so that means if something happens, she’s going to be the one who sentences me to the nine years that’s hanging over my head.

Nearly every single member of the Stinc Team and your immediate family was arrested at one point in connection to the investigation, some for crimes ranging from petty graffiti, to holding guns in videos, to buying clothes with a stolen credit card.

Everyone. My sister, my mom; they even took [Stinc Team member] Bambino’s kids because of the “Shoot a Baby” video. The kids weren’t even there, but they said that since there were guns in the video, it was reckless endangerment to a child or some weird-ass shit. It was one of those “We’re going to take his kids and hopefully he says something about Drakeo.” But there’s nothing to say because I didn’t do shit. Don’t you think if I did all that, someone would’ve said something?

In court, the defense played tapes of Deputy Sheriff Hardiman’s first interrogation of you when he told you your music could be used against you at trial. How much of their desire to pursue the case do you think had to do with the sheriff’s department and prosecution not liking rap music and your popularity?

A lot. The first day that he interviewed me, Detective Hardiman said, “You know I don’t like rap? I told you that, right?” My response? “I can tell.”

Then he says, “I know what you’re going to tell me, ‘This is art. You have to separate art from the artist. It’s not real.’ But that doesn’t matter because when we use these videos with guns and you with your rap lyrics—and those are real guns, you’re going to say they’re prop guns but these are real guns—and when we show the jury music videos with you talking about big 40s and the ‘Choppa make him go ugh,’ the jurors won’t like to see all that.”

What kept you going at your lowest point?

I had letters all over my wall from fans telling me all kinds of crazy stuff like, “You’re going to be so big,” and “Don’t give up,” and “I listened to your music when my mom died and my dad died,” and all this. I was like, “If they’re not giving up on me, then why should I give up?” Once you start giving up, then that’s how they get you. Then they offer you a deal for 30 years to avoid serving life, but it’s like, 30 years? That is life.

What was the darkest moment?

When I went back to court on the 60th day after my verdict and the DA fucking said that they were going to refile charges on me. For the same thing.

Now that we’re at the end of this three-year saga, why do you think you were specifically targeted?

I was a successful Black man that made it out of poverty. They didn’t want me living the life that I was supposed to live. I always said that if I was out here still doing bullshit, fucking around, still carrying guns in music videos, or doing crazy shit, they wouldn’t have given a fuck.

I did that mixtape in seven fucking days, like I’m doing right now. They knew. They didn’t want it to be me. It could’ve been anybody else, but it was me: somebody from the hood who doesn’t gangbang. Everyone fucking gangbangs in L.A. rap; it’s just a part of this shit. I’m the only one who doesn’t and I blew up without any cosign from anybody. They just didn’t like that shit.

In the courtroom November 4, did it feel like you were actually going to get to come home?

I thought they were going to say, “The good news is that you got that plea deal, but the bad news is that you’re not going home.” Then they were like, “Come in here, man. Put this bullshit plastic suit on [to leave].” I was like, “Oh man, it’s real.” Then I thought, “They’re probably going to be waiting outside the door, standing right there when I walk out like, “The good news is that you’re out, but now, we’re going to have to rebook you again.”

What’s been the best part about coming home?

Being in the studio again, making music, clowning around, just being me. It was kind of weird walking in the mall today. I lost my mask, and motherfuckers was looking at me like I was a terrorist or something. I was just like, “Oh man, they’re taking this shit really, really serious.” I left three years ago and now there’s COVID-19, everyone’s wearing a mask, sanitizer everywhere.

What do you hope to achieve career-wise?

To be the greatest, youngest, richest rapper in California. I want people to hear my story. I want people to know that I’m not the first and I won’t be the last person that they try to do this to. It’s not about to stop. They’re just going to try to find another way to do it to somebody else.

How did this make you political?

I wasn’t political when I went in, but I started noticing how all this shit was affecting me. And I was the person with the platform and who actually has a following. How is it going to work for those people who don’t have a following? Who don’t have the ability to pay for a lawyer? If I had a public defender, they would’ve banged me out [sentenced me to life].

How do you think you’ve grown as a person in these last three years?

I don’t take nothing lightly no more. I listen to everything that people tell me. People have shown me who they really are. A lot of people didn’t think I’d get out. Everyone was shocked. It just showed me life isn’t a game. I still feel like they gave me this deal to be like, “Don’t fuck with us. We gave you your life, and we can take it away any time we want to.” All of a sudden, after three years, I’m back.

What do you aspire toward in the long term?

Be rich. Hopefully get my mom and everybody that I can take care of out of poverty. I’ve got to make sure that they’ll never have to want for nothing again. I want to show people that no matter how hard the situation is, my story proves that anything is possible.

A lot of people counted me out. Sometimes even I did. I knew that either I was getting banged out or I was going home; there was no in-between. I never even considered getting offered a deal to come home.

Do you hope to get involved in criminal justice reform?

To a certain extent. I’m not trying to be Malcolm X. I’m still from the streets. I would like people to take the time to go out there and do the research for themselves and see what they tried to do to me. But I’m not trying to be no super advocate.

I’m here now, though, and if you want to know about certain laws, I fought every charge that you can fight—from petty crimes to the most serious, with a gang allegation on every one.

What do you hope that people learn from your story?

First of all, don’t put guns in music videos. Because it doesn’t matter if you put them as a prop, they’re still going to get you for that. Also, you don’t have to possess the firearm. Even if you’re around it in a video, you can still go to jail.

We need to repeal that 182.5 gang conspiracy law too. It doesn’t make any sense at all. It contradicts itself. More people should research that. People might think that it’s the same thing as a gang enhancement, but it’s not.

What’s next in the immediate future?

I’m about to fuck everything over. People tried to tell me, “Bro, I know you’re not about to be humble, but just chill out a little.” I am not chilling out, not even a little bit. I’ve been in jail for a long time and I’ve fought the most serious of charges, and this is just me. This is who I am.

I’m not going to dumb my shit down and I’m not going to be sympathetic to people to make them feel good, because nobody was sympathetic to me when I was in jail. Almost nobody [in rap] posted my case. I’m not being sympathetic to no one, and my tape is going to be really incredible. I have nine songs done already, and it’s only been two days. It’s pretty cool—nine really awesome songs. It’s going to take you through a journey. You’ll know the truth.

Jeff Weiss is the founder and editor of POW. His work has appeared in The Washington Post, the Los Angeles Times, and GQ.


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