Inside Kim Kardashian's Prison-Reform Machine

Over the past two years, Kardashian West has become a force in the world of criminal justice reform. She has successfully lobbied Trump, spent time on the phone with governors and legislators, written letters in support of clemency petitions and paid legal bills for people trying to get out of prison. She has a documentary coming out Sunday on Oxygen, “Kim Kardashian West: The Justice Project,” in which she supports the early release of four people who were convicted on charges including murder.

Kardashian West, 39, is even studying to become a lawyer, taking part in an apprenticeship program that requires 18 hours of legal work each week. She writes memos or motions, reads transcripts and does legal research for a criminal justice reform group called #Cut50. She plans to take the first-year law students’ examination — the “baby bar” — this year.

It’s all a bit unexpected. Kardashian West is at the height of 21st-century celebrity, of famous for being famous. She took her reality show prominence and spun it into a number of businesses and products, including Skims, KKW Fragrance, KKW Beauty and “Kim Kardashian: Hollywood,” a game for mobile devices. She has 164 million followers on Instagram, where she sprinkles some sponsored posts about hair care products, Facebook’s video calling service and, to much internet outrage, meal replacement shakes by Flat Tummy Co. According to a lawsuit she filed last year in which she accused an online retailer of using her image to sell knockoffs of her outfits, she can charge hundreds of thousands of dollars for a single post.

But in recent years she has used that fame to further her activism, blending the two to get results. While Jane Fonda spent her fall Fridays getting arrested at the Capitol to highlight the urgency of the climate crisis, Kardashian West was able to walk into the Oval Office and appeal directly to the president. It helps to know the right people: She counts Ivanka Trump and Jared Kushner among her friends.

For decades, being tough on crime was seen as the only political option in America, which led to a building boom for prisons, long mandatory-minimum sentences and an extremely high incarceration rate compared with other countries. Today, criminal justice reform is seeing increasing bipartisan support, along with a push from celebrities like John Legend and Jay-Z.

The president has embraced it as a signature issue, airing a multimillion-dollar campaign ad during the Super Bowl highlighting sentencing reform he signed into law last year, which the White House saw as a way to appeal to black voters. The ad starred Alice Marie Johnson, a woman he released early from prison after Kardashian West helped plead her case.

Kardashian West’s success is Trump’s success, too.

In such a divisive time, that could be dangerous. In addition to working closely with a president despised by the left, someone many of her fans (and customers) may detest, she’s taking on an issue that, while becoming more broadly palatable, remains charged. As politicians have feared for years, there is always a chance that some people who are freed will go on to commit other crimes.

If what she is doing is helping Trump’s image, Kardashian West doesn’t seem to mind. Her brand, meanwhile, appears to be doing just fine. In the last presidential election, she publicly endorsed Hillary Clinton. But this time around, focused on her justice reform issues, she has said she won’t endorse anyone.

“I do love that I see so many different potential candidates discussing it,” she said, the Capitol building over her shoulder looking a little dingy against the blazing white of her suit. “I will work with any administration.”

As many of us have noticed recently, it’s hard to get work done when your kids are around. So several times a week, Kardashian West would drive — or be driven by her security team — to #Cut50’s Los Angeles offices in a nondescript, two-story building not far from her home. (That was in normal times, anyway, before she stocked an extra house she owns with food, cleaning supplies and toilet paper.) In the office, she would set up shop with her contracts or “crim law” binders and a tiny white chocolate mocha, hot, with whipped cream. She said her army green “school backpack” from Yeezy, her husband’s brand, ripped because her books were so heavy.

“I was never one to like school; honestly, I hated it,” she said. “So the fact that I love it is so shocking to me. But everything kind of pertains to me now” — like contracts, for example, which would have felt meaningless to her in college, she said. “Now I get contracts all the time. So I read them, and I understand how to read them and how to write them. And then criminal law, that’s just what I’m into. That’s superinteresting to me.”

As an apprentice at #Cut50 (the group’s national director, Michael Mendoza, giggled as he called her “our intern”), she must do at least 18 hours of work for them each week, five of which have to be supervised. So Jessica Jackson, one of the group’s co-founders, flies to LA to study with her, where she is joined by a senior counsel at #Cut50, Erin Haney. Both women split their time between the Bay Area and Washington, D.C. They settle into a room where white walls are lined with legal books while Kardashian West takes notes in what Jackson describes as “absurdly good handwriting.” Kardashian West pays for their travel expenses, though these days, they make do with FaceTime and phone calls.

In return for Jackson’s and Haney’s efforts, #Cut50 gets an apprentice with one of the biggest megaphones on the planet and access to her tremendous list of contacts.

“I know my role, that I can be there at the end to push it through,” Kardashian West said. “I can also be a silent partner. I think it’s knowing when to speak out and when not to, and when to privately call,” she added. “People think you need to shout it out on social media and shame people into making decisions, but that’s not how it is.”

Celebrity activism is an American tradition, from Fonda to Harry Belafonte to Mark Ruffalo, who has pushed hard against fracking, and Rose McGowan, who used her personal struggles to fire the #MeToo movement.

A good cause also rounds out one’s image, polishes the brand. Kardashian West said she started hearing she should find one when she first became well known years ago. Publicists suggested Operation Smile, which performs surgery on children with cleft lips and palates, and something about saving the dolphins, she said. And while she hastened to say that both are worthy causes, they didn’t speak to her.

Until 2 1/2 years ago, criminal justice reform didn’t, either. She didn’t know anyone who had been to prison. Her husband, Kanye West, has a cousin who is incarcerated for murder, but she had never met him. She didn’t have a connection to it, she said.

That changed — where else but on Twitter — when she saw a video about Johnson that argued that after more than 20 years, she should no longer be in prison for a nonviolent drug offense. Kardashian West contacted a family friend, a lawyer named Shawn Holley, who worked with her father, Robert Kardashian, on the O.J. Simpson trial, and asked if there was anything they could do. Holley called lawyers (whom Kardashian West paid for, Holley said) while she called Ivanka Trump.

After her initial audience with the president in 2018, outraged think pieces sprung up on the internet, including one in The New Yorker that, while careful to give Kardashian West credit for trying to use her platform to help, described the meeting as “this Boschian spectacle of horrors, this stand-in for the reflective, responsible work of actual public service.” A tweet Kardashian West posted praising Johnson’s participation in the president’s Super Bowl ad this year was greeted angrily by people who considered it an endorsement of Trump.

“People would always warn me, ‘Well, you can’t go into the White House; you can’t have any association,’” she said. “To me, that wasn’t what it was about. I thought, my reputation over someone’s life? It didn’t matter to me about what anyone assumed.”

When Momolu Stewart was serving a life sentence in the Central Detention Facility in Washington, Kardashian West became a topic of conversation. Word spread that she had helped Johnson get released, so maybe she would help them, too.

“You’ve got a lot of guys where that’s all they do: focus on getting out,” said Stewart, who spoke to Kardashian West in the documentary, before his own release.

So people in prisons around the country, along with their family members and lawyers, started writing letters to Kardashian West. And more letters. And more letters. She estimates she receives hundreds of letters a month, sent to her through every available channel, including #Cut50 and her business manager.

They are opened by her security team, sometimes sorted by her assistant or someone from #Cut50, and arrive on her desk almost every day in a neat little stack, most of them written out by hand. She said she reads them all.

To do that, she carves out regular letter time. She’ll often read them at night curled up on a cream-colored banquette in her kitchen, sorting them into piles on a long wooden table, a place where her children do crafts and homework. She keeps an eye out for policy issues #Cut50 is working on, like mandatory minimums, and cases where she thinks she might be able to help. Hyperorganized and a self-proclaimed micromanager of her own time — she likes to keep her inbox at zero and deletes text conversations at the end of the day — she said she tries to keep the stack small so it doesn’t get away from her.

One of those letters ended up in her documentary: the story of a woman named Dawn Jackson. The headlines when she was arrested said that she murdered her stepgrandfather after he refused to give her money. But the story put forward in the documentary is more complicated: He molested her as a child and tried to rape her that day, so she stabbed him.

Kardashian West said that Dawn Jackson deserved to go to prison for what she did, but 20 years later, she is no longer a danger to society and should be able to go home. Her case is still ongoing.

This is not a casual stance to take. It’s easy to say that nonviolent drug offenders who have never had a parking ticket shouldn’t be dying in prison, but Kardashian West is also vouching for people who have committed violent crimes and don’t deny it.

“Doing the documentary, I wanted to pick very specific people — in a sex trafficking situation, in a murder — and really show people that once you maybe get to know their background and their history, you might soften up, too,” she said. “And there’s a lot of people who are really deserving of these second chances.”

Rod Aissa, executive vice president of original programming at Oxygen and E!, said that as an executive producer, Kardashian West was very hands-on — in the story selection, in hiring the showrunner, in watching every cut and trailer. And while the Kardashians are masterful at finding ways to make money, this documentary did not represent such an opportunity, he said. Documentaries rarely do, and in this case, Aissa said the whole budget went into shooting and postproduction.

Perhaps it is here, in the documentary, that Kardashian West’s two worlds flow completely together. Here, she’s on television. Here, she’s a star. But she’s also visiting a prison, dressed modestly in black, and the home of a lieutenant governor talking about sentencing reform, while wearing sky-high snakeskin boots.

It’s undeniable that people will pay attention to Kardashian West — some with admiration, others with skepticism. And some will always be fans.

“Hey, will you do me a favor?” said David Shephard, whose release from prison was chronicled in the documentary, over the phone. “Tell Kim I said thanks for everything.”