“Right now young men who sing and rap and rhyme are suffering for their ability to say what they want to. We all benefit from the artists who push the boundaries of speech, and so as a country we should see a collective interest in protecting them. This is especially true for artists who criticize the state, because once the state — which is supposed to be a representation of the people — is above reproach, we are entering Orwellian waters. That scares the shit out of me.”

Excerpt From Michael Render’s (aka Killer Mike’s) Foreword to Rap on Trial by Erik Nielson and Andrea L. Dennis

In the city of Los Angeles, there’s a man who was tried and found not guilty of murder and attempted murder. But that man currently spends all but seven hours a week locked in solitary confinement.

That man’s given name was Darrell Caldwell. He is better known as the emerging Los Angeles rap artist Drakeo the Ruler. 

At his last trial, the prosecutor, Shannon Cooley, argued that Drakeo’s group, called the Stinc Team, is a violent gang, and then Cooley proceeded to use the artist’s work against him. “As his moniker suggests, he is the leader … They rap about their crimes,” she said.

The lead detective on the case, Francis Hardiman, told the court that he employs “the greatest crime-fighting tools on earth – Google and social media” and explained how he used the artist’s work to build a case against him. 

Although Drakeo was acquitted on the murder and attempted murder charges, he is still in jail because he was convicted on a felony gun charge, because the jury was hung on the counts of gang conspiracy, and because the prosecution intends to try him again. 

Drakeo is in solitary confinement awaiting trial because he posted on social media:


Drakeo’s post provoked some of his fans to post threatening messages towards Detective Hardiman and it was Hardiman who successfully sought to have Drakeo placed in solitary. 

Drakeo’s trial was scheduled to begin last week, but has been postponed until the new year. There has been some excellent coverage of this case. The most intimate and emotionally impactful has been the reporting by Jeff Weiss in The Fader. CRIME STORY will cover Drakeo’s new trial early next year and later this week, we will be posting an article that uses this case to delve into the use of California’s Gang Conspiracy laws to prosecute artists of color. But I would like to take a moment to discuss the political ramifications of this case for the upcoming race for Los Angeles District Attorney.

Jackie Lacey is up for reelection within the next year. It has been well documented that she faces an uphill battle. There is increasing political momentum – particularly in traditionally Democratic communities – behind the candidacies of those who advocate for decarceration, an end to cash bail, prosecution of criminal police officers, and the prevention of police with a track record of mendacity from testifying in court. We cited this phenomenon in The Chrissy Teigen Tweet and Trump’s Turn Away from Criminal Justice Reform

Chesa Boudin, the newly elected District Attorney in San Francisco, is among the most aggressive of this new breed of prosecutors in his ambitions and his planned tactics aimed at meaningful and expedited prosecutorial reform. 

In a recent interview on the Aider and Abettor Podcast, Boudin said, “I want to eliminate racist gang enhancement allegations. I think if someone is in a criminal street gang, and they commit a serious crime, they can be prosecuted for the serious crime. But the way that gang enhancement allegations have been used historically and even currently in San Francisco and in so many other parts of the country is really aimed at criminalizing an entire culture and shoehorning into evidence in front of a jury a tremendous amount of irrelevant but highly prejudicial social media and family relationships… so that’s another thing we’re going to do right away. End the use of racist gang enhancement allegations.”

Meanwhile, Jessica Pishko, a lawyer and writer about incarceration and social justice issues, just last week penned an OpEd in The Appeal in which she suggested that Jackie Lacey “has largely disappointed those who looked to the new, Black, female and Democratic district attorney to enact change. And, over time, once progressive prosecution ideas have become mainstream and Lacey seems woefully behind, in the model of the same tough-on-crime DA that residents had experienced for decades.” Pishko later related the consensus of advocates who feel that Lacey is “in the best position to help regulate some of the worst excesses of the LAPD, a law enforcement agency with a long history of oppressing communities of color, but hasn’t done so.”

While the activist community seems to have made up its mind about Lacey’s legacy, it is not yet clear that the general voting population in Los Angeles is ready to vote her out of office. Yet, just as the OJ Simpson trial revealed a severe disconnect between Gil Garcetti’s DA office and the Los Angeles community, there may be a case that galvanizes the LA voters to take a more progressive turn in the DA election.

If popular LA Hip Hop artists like Dre or Snoop or Kendrick begin to get their fans activated about Drakeo’s case… if Kim or Kanye advocate on his behalf, the blowback on Lacey’s campaign could be politically devastating.

I began this piece with a quote from Killer Mike’s Foreword from Rap on Trial, and I will close with another quote from that same piece:

“Prosecutors know that locking up young men of color carries political capital, and they’ve figured out a way to use rap lyrics to do it. Right now, aspiring rap artists need to know they are being targeted by the authorities, and they need to balance their right to free speech — and their desire to push the envelope of free speech — with the reality that police are watching. ”

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