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In Conversation With John Hamasaki, Attorney for Drakeo The Ruler

Drakeo’s trial, its many cultural implications and the uphill battle for policy change in Los Angeles.

In Conversation With John Hamasaki, Attorney for Drakeo The Ruler
While Angelenos flooded the streets to oppose racism in policing and the criminal justice system, Drakeo was being held in solitary awaiting trial on a charge he’d been acquitted of. (PHOTO: Drakeo the Ruler)

By now, you almost certainly know how the Drakeo saga went down. Born Darrell Caldwell, Drakeo The Ruler emerged as a shockingly original songwriter with vibrant slang and steely delivery. As Drakeo ascended with his collaborators, a crew called the Stinc Team, he became an obsession of LA County Deputy Sheriff Francis Hardiman.

In 2017, Drakeo and the rest of the Stinc Team were hauled in on bogus charges. Hardiman’s office thirstily tried to pin a 2016 murder on Drakeo based on his rap lyrics, Instagram posts and music videos. Drakeo was fully acquitted, but remained in solitary confinement while awaiting a retrial for the same charge he just beat. In short, he was the human consequence of a brazen and prideful prosecution, and the hottest rising rapper in the storied LA hip-hop universe was struck with a literal gag order.

With the help of a spirited legal team and a lot of media coverage, Drakeo was able to beat the gang enhancement case again and regain his freedom. His plea deal was delivered the very night that incumbent DA Jackie Lacy was voted out of office. It’s all really messed up, and it serves as some bizarre triple-beam referendum on our explosive cultural moment, our decrepit criminal justice system and the anti-Blackness that still infests our city. Right now, Drakeo is out of jail…and he’s already dropped two mixtapes to critical acclaim. But none of this was supposed to happen in the first place.

KNOCK spoke with criminal defense attorney John Hamasaki, whose tireless work helped the #FREEDRAKEO push become a reality. We talked about Drakeo’s trial, its many cultural implications and the uphill battle for policy change in Los Angeles.

This conversation has been edited and condensed for clarity. Free the Stinc Team.

“[Prosecutors] knew they were going to lose, and they were worried about their jobs, and that’s why he got a plea deal. I still hope they lose their jobs,” Hamasaki told KNOCK. (Photo courtesy John Hamasaki)

KNOCK: Why should people care about what happened to Drakeo The Ruler? What was so special, or terrifying, about this case in particular?

JOHN HAMASAKI: In some ways, this case was wholly emblematic of the Los Angeles criminal justice system, at least as I’ve come to understand it over the past two years. The disproportionate focus on prosecuting young men of color. The use of gang charges and gang enhancements in a way that is unnecessarily punitive. You know, when you hear about these “reform” movements all across the country, that wave really didn’t reach LA, at least certainly not in practice.

There’s an entrenched culture, and you see that in the reactions: the prosecutors using the media to complain and anonymously source things, and the judges refusing to dismiss charges. It’s a really dominant culture, and there’s just not a strong enough Public Defender’s office. There are plenty of great public defenders and criminal defense attorneys in LA, but there’s been no united pushback against this carceral approach.

I come from San Francisco, where we had a very strong Public Defender’s office. Constant fighting and pushing back against the prosecution, but in an organized fashion. One attorney can’t take on the DA’s office, although I gave it my best shot, hah. Really, you need a reform-oriented united front to go against an organization like the LA District Attorney’s office.

KNOCK: Had you seen or worked on anything like this case?

JOHN HAMASAKI: This was unique because they were prosecuting a rap group as a gang. They wanted to make this rap group into a gang, even though they were clearly not. LAPD and the Sheriff’s “gang experts,” whatever that means, they took the stand and all said they hadn’t heard of [the Stinc Team] as a real “gang.” Folks don’t understand how these laws can be abused in this way. They can prosecute three or more people, with a common sign or symbol, that are accused of a crime…even if that crime is not “gang related” at all. In this case, we’re talking REAAALLY low-level criminal activity from some people associated with Drakeo. Vandalism, tagging, but nobody shooting or killing or anything like that.

There’s a developing trend, in media and academia, on the use of rap lyrics in criminal proceedings. As I started talking to Drakeo and the people around him, I realized that this case was really as crazy as everyone was describing. The way they were prosecuting this was just insane. Not the types of evidence that you’d typically see, and really, just a lot of focus on Drakeo. Him, his lyrics, his music videos…they wanted to show that he was a bad guy because he rapped about guns, street life, lean…there was an inability to separate art from reality, and that was bizarre.

After the first trial, they started to realize how ridiculous this all looked. The infamous Detective Hardiman was still pushing this, prosecuting Drakeo for being a famous rapper, even as everyone was talking about how insane it was.

There’s a degree of anti-Blackness. I don’t like to just yell “RACISM!,” but the prevalence of it in the LA District Attorney’s office was really shocking to me. The way it’s just part of the culture. They think they’re “getting the bad guys.” They’re abusing laws, to punish the people that weren’t the intended focus of these laws, and then they’re expanding the laws to ridiculousness. This Drakeo case became, like, a trophy prize for that office. Steve Cooley’s daughter was the one doing the prosecution. It was supposed to elevate her, and she ran for judge using this high-profile case as a platform…it became very political. Like, why did they file “special circumstance” charges, which made Drakeo eligible for the death penalty? He had no serious priors, just low-level stuff: the standard interactions with the criminal justice system in South Central.

Jeff Weiss’ article really forced the DA’s office to dig in, and it made the case a lot harder on everybody. After we soundly beat them at trial, with two charges hung 10–2 and 7–5 for acquittal, the office chose not to dismiss it but actually doubled down. They brought in who they thought was their best trial attorney and dug all the way in. No plea deals or offers for time served or anything like that, they went with these really tenuous theories of liability and weak evidentiary charges. And that’s how it was set after the first trial.

KNOCK: What’s wild is everyone knows Drakeo The Ruler, because he makes unique and awesome music. But precious few people know Darrell Caldwell the person, the actual human consequence at the end of all this. That must have tripped you out.

JOHN HAMASAKI: If he wasn’t Drakeo The Ruler, this case would have never been prosecuted. It was appalling, shocking, horrifying that he had to go through all that just because he found a way to succeed as an artist. His type of art was not seen as art by the police or the prosecutors. They think he’s rapping about violence, therefore he must do violence. I think some of them actually believed that. Like, Hardiman really was not able to distinguish art from reality, fact from fiction. It seems so far-fetched…and there’s an aspect to it that’s really offensive, the mere idea that you’re not allowed to use or make art without it being subject to the criminal justice system.

KNOCK: How much of this was about the general ‘Defund the Police’ climate of 2020 and the specific District Attorney race going on in LA?

JOHN HAMASAKI: If this case hadn’t achieved the media notoriety that it did, and quite frankly, if I didn’t come on this case, Drakeo would be doing 25-to-life. He had a really incompetent lawyer focused on the wrong things. I’m not anybody special, but it was the type of case that I knew how to litigate and win. My first appearance in this case was the first day of trial. It was disturbing to think that Drakeo was gonna be the next great young rapper locked up. I’m getting pissed off again just recalling this. It never should have been prosecuted.

I think without George Floyd, Breonna Taylor, BLM-LA and the momentum lent to George Gascón, we would still be in trial right now. I believe he would have been acquitted in trial, but certainly not out on the first day. I think Gascón ran a really good campaign, but it all really shifted when this movement happened in the spring and the summer. His case is now part of a first wave of reform that’s coming. I think prosecutors were scared to still be on the case when Gascón came in, and the gang stuff would be dismissed. They knew they were going to lose, and they were worried about their jobs, and that’s why he got a plea deal. I still hope they lose their jobs.

KNOCK: Any memories from the court victory? Or that first night Drakeo got out?

JOHN HAMASAKI: When they approached us that night about a plea deal, we didn’t really believe them, because they had been so dishonest throughout this process. And Drakeo shouldn’t have had to take a plea on anything. If they had any degree of ethics or competency or respect, he wouldn’t have gone through all this. And he’s still on probation, though we’re trying to get that terminated. He went to the studio that night, and I went along to observe the end of this two-year journey.

It was really powerful to see him back, making music in his element and putting his life back together. He’s focused on music. I’m really looking forward to seeing him grow, as an artist. He’s getting a lot of attention, a lot of people asking for collaborations and so forth, and I expect that to continue. Before this case, I didn’t know Drakeo. My taste in rap is old school, a few decades before. So to see how powerful and influential he is right now, it was really special.

KNOCK: That previous generation of LA rap, Ice-T and Ice Cube and Death Row and the Dogg Pound…the music has gone through stylistic and cosmetic changes, but the subject remains the same. It’s still anger toward the LAPD.

JOHN HAMASAKI: The culture is changing, but the criminal justice system hasn’t. That includes LAPD, LA Sheriff’s Department, LA District Attorney’s office, the courts and judges…they all come from prior eras, when Los Angeles was really racially divided. The police and the prosecutors have traditionally been involved in enforcing those divisions, especially with keeping Black people out of certain spaces.

That leadership is still there, and even though we as a culture have evolved, the system has not. Truthfully, working in certain parts of LA feels like practicing cases in the Deep South. It’s that strong. Compton is still in a different era, in the way that Black and brown people are treated. And if you look historically, that’s what our criminal justice system was designed to do. That’s not shocking. What’s shocking is that it hasn’t changed. There’s a saying in police oversight that culture eats policy for lunch. You can put the best policies in place, but it’s going to take a real long time to change the culture.

There’s a lot of blame to go around in LA. No one in power gave a shit about this. All the institutional Democrats were endorsing Jackie Lacy until George Floyd protests started. It’s a long, long fight coming in LA. Those forces are here, institutionally. They’re not going to give up on the way things have been, right?