Why Drakeo the Ruler's Legal Battle Should Concern Us All

After a three-year fight for his freedom, the rapper was released last month. His lawyer explained what Drakeo's story says about our justice system.
Ashwin Rodrigues
Brooklyn, US
Drakeo the Ruler
Photo by Fernando Matamoros, Illustration by Dessie Jackson
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On November 4, 2020, Darrell Caldwell, best known as Drakeo the Ruler, was freed from Los Angeles County’s Men’s Central Jail. It was a sudden turn of events: his release followed the first day of resumed trial proceedings, prolonged by an aggressive prosecution and COVID-19 delays. Drakeo provided the following statement to VICE via his publicist: "We know the Truth. The truth is undisputed. #DrakeoFree."


Yesterday, on December 1, Drakeo released We Know the Truth, an album recorded shortly after his release. The album features longtime collaborators Ketchy the Great, Rio Da Yung OG, and Ralfy the Plug, and high profile verses from Tee Grizzly and Lil Yachty. Across 18 tracks, Drakeo tells his story, drawing from hundreds of pages of material written while he was incarcerated. 

In 2017, Drakeo was arrested for murder, attempted murder, and conspiracy to commit murder, relating to a 2016 shooting at a party in Carson, California, that left one dead and two wounded. The prosecution did not accuse Drakeo of pulling a trigger, but alleged that he orchestrated and provided the weapons to murder a rival rapper, who did not attend the Carson party and was not injured.

Hip-hop fans recognize Drakeo the Ruler and associated rappers in the Stinc Team as generational talents; the prosecution argued the Stinc Team was a gang and that Drakeo was the leader. The trial resulted in Drakeo’s acquittal on the counts of murder and conspiracy to murder, but the jury was hung on the counts of criminal street gang conspiracy and shooting from a motor vehicle. The District Attorney subsequently refiled charges on these last two counts. Leaning on California's Street Terrorism Enforcement and Prevention Act (STEP), the prosecution focused on portraying Drakeo as a gang leader.

While Drakeo was ultimately released, his case is worth a close look. His lawyer, John Hamasaki, says it highlights excessive overreach, a willingness to overlook conflict of interest, and the disturbing practice of using rap lyrics and social media posts to create a narrative that served the prosecution but didn't necessarily represent the truth. 


"It really makes no sense, logically, from a criminal justice perspective," Hamasaki said regarding the pressure the District Attorney's office exerted on his client and the Stinc team. As for the group's classification as a gang, "their main crime was making music, videos, and raps. And those raps were offensive to the [lead] detective."

In part of a lengthy response to VICE laying out the details of the case, the Deputy District Attorney, Phil Stirling, said, "The reasons for the jury’s verdicts are too complicated to explain herein," with regard to the first trial. "In light of the evidence, a decision was made to re-try the case. It 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."

Using rap lyrics as prosecutorial evidence contradicts the concept of artistic expression under the First Amendment, but there are historical and contemporary examples that show it's a norm, not an exception.

In 1996, prosecutors alluded to Snoop Dogg's "Murder Was the Case" in the closing arguments of his murder trial, for which the rapper was acquitted. In 2001, Mac Phipps, a rapper on No Limit Records, sat in court as the prosecution recited his lyrics, sometimes actually rewording bars to sound more menacing.


Phipps is still in prison serving a 30-year term for a crime someone else admitted to, as detailed on the Louder than a Riot podcast, and in the first chapter of Rap on Trial: Race, Lyrics, and Guilt in America, by Erik Nielson and Andrea L. Dennis. In 2012, the Pennsylvania State Supreme Court found Jamal Knox, known as rapper Mayhem Mal, guilty of terroristic threats and witness intimidation for lyrics in his song. Michael Render, known as Killer Mike, along with Nielson and other legal scholars, filed a 32-page amicus brief to the Supreme Court related to this case. The brief contained a historical introduction to hip-hop, the difficulty of interpreting the art form, and the threat to free speech posed by the ruling. The Supreme Court declined to hear the case.

Nielson has served as an expert in Hamasaki’s previous defenses and other trials where rap lyrics were involved, including Drakeo's first case. "The fact that Nielson is a middle-class white guy in a suit talking about hip-hop," Hamasaki told Pacific Standard in 2016, made it easier to convince white jurors "that people from inner-city, lower-income families are capable of producing art." (In the case covered in Pacific Standard, in which Nielson testified, the plaintiff was acquitted of a murder charge but convicted of two lesser crimes.)

Law enforcement's punitive fixation on hip-hop goes beyond malicious interpretations of art. The NYPD's infamous "hip-hop cops" targeted New York's drill rap scene, viewing concerts and video shoots as possible gang-related events. This targeting has prevented artists from needed and deserved income streams.


"High-profile cases often don't go the normal route that other cases do," Hamasaki said. "If Drakeo was not an up-and-coming rap star celebrity, he never would have been prosecuted. I've never seen somebody prosecuted on facts like these." 

Hamasaki said the prosecution misclassified art as statements of intent, in part because the narrator was a young Black man from South Central Los Angeles. He also felt the prosecution was looking to make their name by attaching themselves to a larger figure in Drakeo. 

"You're not supposed to get your fame by committing a horrible injustice on somebody else," Hamasaki said. "And that's honestly how I felt this case went." 

Hamasaki, who previously lived and practiced in Northern California, moved down to Los Angeles after joining Drakeo's defense team last year. In addition to pointing out the tenuous connections made by the prosecution's interpretation of rap lyrics, his defense identified foul play, Hamasaki said, like the use of a fake subpoena, and an undisclosed conflict of interest on the part of the prosecution. The lead detective, Francis Hardiman, is married to a member of the District Attorney's office, Hamasaki said, which was not disclosed at the first trial. "When you have a witness that is actually, through the spouse, getting close to $300,000 from that office, that's a conflict."


Stirling said "there are many members of local Los Angeles county law-enforcement (LAPD, LASD and other smaller agencies) that are married to people that work within the DAs office. It is only a conflict of interest if they have worked or work on the same case. So long as they’re not assigned to the same case, it is not a conflict of interest." He added that the subpoena was not fake, but rather had been 'legally modified by hand' to change the date, but acknowledged that prosecutors had not understood the situation 'as well as they should have' when they had the witness arrested for not being willing to appear in court on the modified date. Stirling said that Judge Walton, who heard Hamasaki's motion, "easily found no conflict of interest" and ruled there was no legal basis for disqualification.

When VICE reached out to Francis Hardiman for comment regarding the case, the LA Sheriff's Information Bureau responded and said "there is another defendant left to be adjudicated, and Homicide Bureau respectfully declines to comment on pending cases." 

Hardiman referred to Drakeo's "Flex Freestyle," in which Drakeo raps about fellow rapper RJ being "tied up in the back" of his car, as a way to accuse Drakeo of conspiring to murder RJ on that night in 2016. RJ himself said he doesn't believe the theory. When Drakeo published a tweet declaring he didn't want to rap anymore because his lyrics were being used against him, he signed the post off with "#THANKDETECTIVEHARDIMAN." One fan then allegedly sent Hardiman a death threat, which Hardiman then used in a sealed declaration in January 2020, used by the court and the prison to place Drakeo in solitary confinement for eight months, which Hamasaki only discovered in July. Hamasaki said Hardiman used his previous experience as a jail deputy to make a request for limitations on Drakeo that could only be satisfied by placing him in solitary confinement. In Stirling's statement to VICE, he said "It should be noted that the defendant had significant ‘day room’ access and never complied with the order restricting his privileges."


Though Hardiman was a prominent character in the trials and media coverage, he wasn't the only part of the prosecution that Hamasaki viewed as a bad actor.

"Because of media and publicity, this was the case that was followed by the highest levels of the office. Those levels of the office approved of this behavior," he said.

But at the beginning of the latest trial, there was a sudden change of heart from the prosecution, which allowed Drakeo to go home last month after striking a plea deal in which Drakeo had to admit the Stinc Team was a gang and plead guilty to shooting from a motor vehicle with a gang enhancement—which imposes a harsher punishment. He left the jail with credit for time served. 

Hamasaki said he had expected a two-month trial. "The media was interested and following, the gag order was lifted, and we were going to beat them up in every way humanly possible for two months. I think they made a decision that that is not something they wanted to be a part of; it probably wouldn't be very good for the careers of the district attorneys involved."

Through long days in court and long nights preparing for proceedings, Hamasaki became familiar with the Los Angeles justice system, and it shocked him. 

"I would not think LA would be like this. It's the worst that I've seen in California. The degree of fair play and ethical conduct that we would hope to see in our criminal justice system—in this case at least—was entirely absent." 


LA County District Attorney Jackie Lacey recently lost her reelection campaign to George Gascón, who ran as a reformer aiming to bring more accountability to law enforcement. According to Hamasaki, Gascón does not support the types of cases brought against Drakeo, which is another possible reason for the suddenly expeditious resolution. Hamasaki credited the Black Lives Matter movement for changing the tenor of the DA race, as protestors stood outside Lacey's office weekly—for three years—in a call to fairly prosecute officer-involved shootings. 

Much of Drakeo's media attention came from journalist Jeff Weiss, who closely followed the rapper's rise, the court proceedings, and the alleged inhumane conditions the rapper faced in Los Angeles Central Jail. Weiss published on his own site, Passion of the Weiss, as well as in Tablet Magazine, The Los Angeles Times, and other publications. He extensively covered Drakeo's 2019 trial in a lengthy report for The Fader that was equal parts enraging and scathing. Through the process of highlighting Drakeo's struggle, he became part of the story. Weiss also published the first post-jail interview with Drakeo in The Ringer. 

Hamasaki, who became close with Weiss over the past year, mentioned The Fader story in his last court appearance, in which he made an hour of arguments in an attempt to disqualify the prosecution. In response to Hamasaki's motion, Stirling said the judge ruled there was no legal basis for disqualification. But either way, after the arguments, Hamasaki said, the prosecution reached out to make a deal.


"That article, and the way they were portrayed, motivated the District Attorney's Office, but not in a good way," Hamasaki said. Instead of looking at the article as an opportunity to "look inward and think about how to do it better next time," Hamasaki said it became motivation to "deprive [Drakeo] of every aspect of humanity, put him back in solitary confinement, gag him, punish him, try to humiliate him, try to degrade him. That is a reflection of the cruelty that exists within Lacey's office," Hamasaki said.

In response, Stirling said: "The January 2019 order, which pre-dated my involvement with this case, simply sought to limit the defendant’s outgoing jail calls to his attorneys only, and had nothing to do with the defendant’s housing status. The Sheriff’s Department, which controls the jails, then, in an effort to comply with the judge’s order, moved the defendant to a single-man cell." 

Hamasaki, who pointed to Hardiman's experience as a former jail deputy, said Hardiman's declaration asked for restrictions that could only be satisfied by placing Drakeo in solitary. 

In a statement to VICE, Weiss described what happened to Drakeo as "a tragedy on all fronts, but at least, it's one with a happy ending. For now. The system continues to keep their talons in parolees. Any minor slip up, even a photo with a friend who happens to have gang ties, can send Drakeo back to prison at the discretion of his judge." 

"Few things have ever felt more surreal or joyous for me than to see Drakeo suddenly free after these years of infernal torture," Weiss said. "The proximity to the election of George Gascón as LA district attorney was unmistakable. It was a victory for collective organizing, grassroots movements, and the power of a free press. More importantly, it's a testament to Drakeo's will to survive the ostensibly unthinkable, and emerge stronger than before." 

Even after he was acquitted of the most serious charges, including murder, "the DA's office opted to keep him in hell for another 15 months," Weiss said. "It proved once again how in America, justice is a lofty idea but one rarely realized."

During a time when his poetic license was being used as a part of a case designed to steal his freedom, Drakeo rapped an entire album over the phone, titled Thank You For Using GTL. On November 4, Both Weiss and Hamasaki greeted Drakeo at Los Angeles Central jail, and later Drakeo hit the studio to record as a free man, equipped with a manilla folder of over 200 songs he'd written while incarcerated.

"It made me incredibly happy to see the culmination of all of this," Hamasaki said. "After his music had been used against him, to see him back where he belonged, in his environment, doing his thing, was really a beautiful moment.” Drakeo was still recording when Hamasaki left the studio around 12:30 am. 

To be freed, Drakeo had to plead guilty after spending three years behind bars, with months in solitary confinement. On We Know the Truth, he covers both his wins and losses: not getting mail in jail, "not guilty" verdicts, a DA who wanted to fight Drakeo after he beat him in trial. On "Captions," Drakeo makes a clear statement, and a reminder that music is music, not testimony. "They're talking about some shit that didn't happen. I can't believe they almost made me stop rapping."

'We Know the Truth' is streaming right now on all platforms.