When he wasn’t imposing new tariffs or breaking up with Elon Musk, Donald Trump spent last week on a bit of a get-out-of-jail-free spree, pardoning and commuting the sentences of fellow shady reality stars and tax evaders as well as former Chicago crime boss Larry Hoover.
Kanye West, who has been a public Hoover advocate for years, posted on X in celebration: “Thank you Drake for helping to bring Hoover home.” Confused? We’ve got you.
Related: Everything to know about Drake’s “Not Like Us” lawsuit
Who is Larry Hoover? Fifty years ago, Hoover founded the Gangster Disciples, a notorious street gang with origins in Chicago’s South Side neighbourhood. In 1973, he ordered the murder of a rival gang member—a crime that landed him a 150-to-200-year sentence in an Illinois state prison. According to federal prosecutors, Hoover continued to run operations from behind bars, resulting in a second federal sentence in 1997.
Why did Trump commute his sentence? Because Kanye West asked him to. Cast your memory back to that infamous 2018 press event when West wore his MAGA hat to meet with the then-and-future-POTUS. The topic of the day was prison reform and criminal justice, and Hoover’s case was one of the focuses.
Does Hoover deserve a pardon? We’re going to go ahead and plead the proverbial fifth—the debate is complex and delves deep into racial bias and the US justice system. It’s worth noting, however, that multiple Black commentators have characterized Trump’s pardoning of Hoover and other Black celebrities as a ploy to curry favour with voters as he pulls funding from programs meant to actually address racial injustice in the prison system.
Okay, but what does Drake have to do with any of this? West’s thank-you post on X included an image of himself and Drake at their “Free Hoover” benefit concert, a 2021 event that was sponsored by Amazon. It was also hailed as the official quashing of a years-long beef between the two rappers (although the unofficial quashing appears to have happened in the lead-up to the show, at a private bash at Drake’s Toronto mansion).
At the moment, their beef appears to be in remission. Yes, West did appear on a remix of Kendrick Lamar’s chart-topping diss track “Not Like Us.” But then, this past April, he showed his support for Drake’s civil lawsuit against Universal.
It’s unclear whether Drake has any connection to Hoover beyond West and that one concert. Instead, he seems to be devoting his own pardoning efforts to Canadian rapper Tory Lanez, who is serving a ten-year sentence for shooting Megan Thee Stallion in the foot in 2020. Unlike Snoop Dogg, Drake has yet to comment publicly on Hoover’s pardon.
So is Hoover going to be released? Not quite. Trump commuted Hoover’s federal sentence, but the president doesn’t have the power to commute a sentence imposed at the state level, so Hoover will remain in prison for the foreseeable future. The charges keeping him there are currently being contested, though, and it’s possible that a federal pardon will move the dial in Hoover’s favour. But, for now, he isn’t going anywhere.
But didn’t West thank Trump for freeing Hoover? His exact post read, “WORDS CAN’T EXPRESS MY GRATITUDE FOR OUR DEVOTED ENDURING PRESIDENT DONALD TRUMP FOR FREEING LARRY HOOVER.” So, yeah, maybe somebody needs to break the bad news.
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Courtney Shea is a freelance journalist in Toronto. She started her career as an intern at Toronto Life and continues to contribute frequently to the publication, including her 2022 National Magazine Award–winning feature, “The Death Cheaters,” her regular Q&As and her recent investigation into whether Taylor Swift hung out at a Toronto dive bar (she did not). Courtney was a producer and writer on the 2022 documentary The Talented Mr. Rosenberg, based on her 2014 Toronto Life magazine feature “The Yorkville Swindler.”