This story was co-published with the Marshall Project.
Early one May morning, Renea Royster arrived at her son's apartment, pulled out her laptop, and scrolled through the dozens of messages from prisoners that had collected in her inbox overnight. She began her daily grind of copy-paste—moving messages sent via CorrLinks, an email service available to federal inmates, to the Facebook pages they had paid her to create in their names.
Renea read out a post that one of her clients had asked her to put on his Facebook page. It was a paean to Hillary Clinton. "Everybody stops and looks her way, and when she talks everybody shuts up and listens," she read aloud to her son Phil, who chuckled. "That's the other type of shit that makes me hard-up! Go Hillary! You are one bad bitch!"
Eventually, she drifted to other tasks: helping prisoners look up old friends, sending them stock quotes and sports scores (for their fantasy leagues), and checking crowdfunding pages where they're raising money for legal bills.
This is what Renea, who is 47 and lives outside Toledo, Ohio, does for up to 100 hours a week, stopping only for new Game of Thrones episodes and smoke breaks and calls from her boyfriend, Jimmy, who is currently incarcerated in Kentucky and who she met through the business.
She recently made roughly $1,500 in two weeks, a solid bump up from her last job at a Walmart deli.
She has coined her operation "Bridging the Gap." It began more simply as a website and Facebook group soliciting pen pals for prisoners who submit a picture, a bio, and a fee. Such sites have existed since the 1990s, and there are now nearly 50, in addition to dozens of Facebook and Yahoo groups that together boast more than 100,000 free-worlders looking for incarcerated people to write.
Renea has become part of a network of small businesses that help prisoners keep in touch with these pen pals, in addition to friends and family on the outside. She exchanges favors with Pigeonly and Infolincs—two start-ups founded by former prisoners that allow people on the outside to upload pictures and text with their phones, and then print and send those images to loved ones inside. Other businesses, like Inmatefone and Phone Donkey, sell forwarding numbers so prisoners can avoid long-distance charges.
She sees herself as a social secretary for people who have been deprived of the forms of communication that are now ubiquitous almost everywhere except for prisons. When her son Phil, 23, is asked what she does for a living, "I say my mom's a secretary for federal inmates... Basically anything they want us to do, we can do it." Phil's specialty is getting the prisoners on dating websites, helping them meet women, and then explaining to those women that their new acquaintance might not be able to grab that drink for a while.
To help get the word out about her businesses, Renea has cultivated a network of prisoners who hand out her flower-laced business cards and post her bright pink flyers ("Ask about our Monthly Specials!") in prison common areas. She recently made roughly $1,500 in two weeks, a solid bump up from her last job at a Walmart deli.
She'll be your personal assistant—one man had her research Medieval England so he could write a novel set there—for $125 a month. She also sells "compound pictures," print-outs of scantily-clad women, for 55 cents each, to men who sell them inside for a mark-up. She maintains your Facebook page for three months for $50.
Prisoners send messages to family members over and over and don't get responses.
Sipping from a big cup of iced tea, Renea handed Phil a stack of pictures to scan and post of men and women looking for pen pals. The posts, which cost $20 for three months, typically feature a few photos—often shirtless—and bios that read like dating classifieds ("I'm a very fun and exciting person to be around! Some of my passions include writing poetry/novels, exercising, cooking and training dogs.").
She then toggled over to one client's Facebook account, where a woman had sent a naked picture, not knowing he couldn't see it. Renea typed a description of the image into CorrLinks to the man.
A little later, she got a message from the prisoner asking her to respond for him: "Dayammmmmmmmmmmmmmmmm baby!"
According to Renea and creators of other, similar sites, free-worlders have several motivations for writing to prisoners. Adam Lovell, founder of WriteAnInmate.com (widely acknowledged to be the largest, with more than 10,000 profiles), said the earliest sites were hosted by churches, promoting correspondence with a prisoner as a form of ministry. "Members of each religion seek out pen pals from the same faith," Lovell said. Other sites, like Black and Pink, which calls for abolishing prisons, frame communication with prisoners as a kind of political work.
Then there's what psychologists call "hybristophilia," a sexual attraction to the men and women behind horrific crimes. Charles Manson, Ted Bundy, and Scott Peterson all received marriage proposals. The site, "Ask a Convict," has a "serial killers" tab, and founder Jon Nolan said that while some people do harbor unsettling romantic proclivities, others are just curious to ask questions like, "What is it like to kill someone?" Nolan was initially curious, too, but eventually, "it got pretty dark and depressing," and he would get letters featuring "a run-on sentence about wanting colored pencils and enjoying strangling women."
He eventually abandoned the site, though it is still online.
Renea's theory about her own site is fairly basic: women like "bad boys," and some women (including her) are particularly empathetic to men society has shut away. Prisoners often ask Renea and Phil to post photos that usually show off tattoos, bulked-up arms, six packs, and scowls. Bios sometimes reveal a lack of subtlety. "They'll write in all caps-lock," Phil said. One wrote in his profile: "I can't wait to hear from a sexy lady with a big booty." Another: "My best feature is 11 inches, uncircumcised."
Renea interprets such talk as evidence that their romantic side has atrophied in prison. "Sometimes you just want to cry because they are so desperate," she said, and she has seen their loneliness manifest in all sorts of ways, from misplaced romance ("In two days they are telling you they love you") to false grandiosity (many tell her they're famous rappers). And she sees the sources of this loneliness, too; prisoners send messages to family members over and over and don't get responses.
Renea also sees a lot of drama; girlfriends who get mad about a new girlfriend appearing on the Facebook page, women who tell multiple men on the outside that they're "the only one" and then do damage control when the truth comes out. Scams are widely known to be common in the world of prison pen pals. In 2004, ten female prisoners in Pennsylvania received roughly $260,000 from hundreds of men who they'd pretended to fall in love with.
"This is the perfect job if you like gossip," Renea told me. "It's like reading the Enquirer every day."
Renea found her first pen pal, Wayne, in February 2015. She had spent her life in small towns on the outskirts of Toledo, working the kitchens at truck stops and nursing homes. Growing up, much of her extended family was buttoned-up and church-going, and she often felt like an outcast, with her nose ring and tattoos and two kids by two men.
After Phil moved out in 2014, she started to feel more lonely. Her younger son, Damian, who is now 16, was in and out of trouble at school. Her latest boyfriend had become "more of a roommate." Communicating with prisoners, on the other hand, was an appealing outlet because there was a comfort in the limitations—she wouldn't "have to worry about them getting out and coming over" or having to explain to her boyfriend why she was talking to other men.
Initially, Wayne tried to flirt aggressively, asking her to send him a picture and talk about sex, and she was cold to him in response. But she wouldn't cut off contact. "I don't want to hurt anyone's feelings, so I just put up with him and we grew together through talking," she said.
He knew about people on the outside who earned money helping inmates post pen-pal ads and run Facebook pages, and he suggested they go into business together. He made up a flyer and told his friends.
In a few months, she had hundreds of men and women sending her profiles and asking about other services. The Department of Justice, which runs the federal Bureau of Prisons, forbids circumnavigating CorrLinks to convey messages between prisoners and third parties. She was initially spooked by a threatening letter from the department, but they haven't taken action. Facebook officially bans people from running accounts on behalf of others, but only shuts down an account if a prison asks them to do so*.
"When I first wrapped my arms around her to hug her, I felt a tingle enfold my whole body." —Jimmy Leach
Last August, a prisoner named James Leach, who goes by Jimmy, asked Renea to place a pen-pal ad for him. Their clipped, professional messages quickly drifted towards the personal. Jimmy, 38, told her he had been in and out of foster care, juvenile facilities, and adult prisons since he was seven years old. He is currently serving a 17-year sentence for possessing a gun "in furtherance of methamphetamine trafficking." He and Renea realized they have the same birthday, nine years apart. Wayne gave her advice on how to stay professional, since many of the men, starved for contact, assumed she was interested in them. "She had a tendency to call people 'sweetie' and endearing terms like that," Wayne said in an email, but "guys in prison misconstrue terms like those." She admits she can't stand to hurt their feelings.
Within days, they were talking to one another like any old couple. When Jimmy complained he was not receiving the right medications for his back pain, Renea fired off an angry letter to the prison. They got tattoos with each other's names. Renea's younger son, Damian, has struggled with mental-health issues and had some run-ins with the law. "He started mentoring Damian, saying how it was just like his life when he grew up," Renea said. Before long, Damian was calling Jimmy, "Dad."
Jimmy is housed at the Federal Correctional Institution in Manchester, Kentucky, about six hours from Renea. On Mother's Day, Phil rented a car and drove her to see him in person for the first time, nine months after they'd first met.
"When I first wrapped my arms around her to hug her, I felt a tingle enfold my whole body," Jimmy recalled via email. "I gave her a quick kiss at first, 'cause it has been eight years since I have had that human contact." They held hands. He noticed her perfume.
Jimmy's official release date is not until 2025, but Renea is already preparing for him to eventually come live with her.
When she returned from visiting Jimmy, Renea had dozens of messages waiting—men asking her to update their Facebook profiles, to post a new picture to their pen-pal ad. But some of the tasks were more simple. One prisoner asks her to check in and say hello after he wakes up and before he goes to sleep. Renea said he told her, "It's just so nice to have someone to say good morning and good night to."
Renea doesn't charge him.
*Renea primarily works with federal prisons. In state prisons, laws and policies surrounding pen-pal solicitations and social media vary widely. South Carolina has punished dozens of inmates with solitary confinement for maintaining social media accounts. Michigan, on the other hand, has no official restrictions. People who run pen-pal websites say some states have tried to ban inmates from soliciting pen pals—usually in the wake of news that a particularly infamous criminal is doing so—but enforcement is spotty.