Sydney Leathers Lived in My Apartment for a Week
Anthony Weiner's notorious sexting partner visited me for my college graduation.
Photos by Amy Lombard
“Goodbye, city I own!”
New York businessmen and 16-year-old rich, white kids who think they're gangsters regularly scream these words—but for once a 24-year-old girl was screaming, and that girl was Sydney Leathers, Anthony Weiner’s notorious former misstress who face-palmed his mayoral campaign when she leaked sexts he had sent her.
In late May, I rode a Metro-North train with Sydney from New York City to Bronxville, New York. Sydney had flown to New York from her home Indiana to attend my graduation from Sarah Lawrence College.
When I enrolled in Sarah Lawrence, I never expected a politician's mistress to attend my graduation from America's most expensive lesbian liberal arts college. I thought my parents would come and applaud as I walked across the stage. But then, in January, everything changed. After years of on-again-off-again fighting, I felt like I had no choice but to briefly become estranged from my mother. It was my choice, and I assumed my mother wouldn't attend my college graduation. I wasn't happy about the predicament, but at the time, it seemed like the right thing to do.
Around the same time, I interviewed Sydney over Skype about her failed attempt to auction her jarred labia following a labiaplasty. When Sydney saw me tweet that none of my biological family members would attend my graduation, she contacted me and told me not to worry. She would come to my graduation and be my “new mommy.”
Sydney said she related to my troubles because she has a difficult relationship with her mother, Laura Leathers. (Yes, that is her real name.) Thanks to intense childhood trauma, Sydney suffers from PTSD. Sydney wouldn't go on the record about what she went through, but she said, “My mom put my oldest brother and me in a pageant, but not my middle brother,” Sydney said. “How fucked up is that? Now look at me! I’m a grown-up JonBenet Ramsey.”
Impulsively, I invited Sydney to live with me for a week.
Many of my friends called me crazy for inviting an IRL stranger—let alone a stranger who is best known for sexting a politician and trying to sell off her labia—to live with me for a week. But having to stop talking to my mother also seemed pretty insane, so living with Sydney seemed like a great idea to me.
When Sydney arrived at my Brooklyn apartment late one night, she strutted into my building, struggling to drag her huge suitcase behind her. She told me how she paid hundreds of dollars on a cab from JFK to Bushwick.
“You've been ripped off,” I said.
She cursed, but didn't seem surprised. Sydney knows she's both a knowledgeable, old soul and very naïve.
A few weeks before Weinergate unfolded, Sydney flew to Texas to attend rallies supporting Wendy Davis, and she was originally known on the internet for running a popular politics blog read by some Washington, DC, power players. (To prove this to me, she agreed to show me old conversations between her and DC figures who read her blog, as long as I promised not to publish their names.) Sydney said she loved politics because she thought politicians wanted to help poor people: “I was that naïve.”
Today, Sydney surrounds herself with few political acquaintances. The second night of her stay, she took me to the Outback Steakhouse to meet some of her New York friends: Greg, a comedian; the novelty song performer Adam Barta; CrackDoubt, a girl Sydney met at a porn convention; and a feminine guy CrackDoubt claims is straight.
When Sydney first met CrackDoubt, she sold sex toys for a living, but CrackDoubt now works as a cam girl. Over a Bloomin' Onion and in between puffs on her vape, she asked Sydney to help her set up her pricing system. Sydney helped her fix her pay system and then Sydney told her about the first time she squirted during sex: “The first time I squirted, I squirted blood. Of course it happened in Baltimore.”
Sydney’s overshare made me feel comfortable so I tell her about a hookup I recently had.
“Did you swallow?” Sydney asked.
“I don’t swallow.”
Sydney started screaming.
“I will swallow when I blow someone I love,” I said.
“You don’t need love to guzzle cum!”
“That was me!” Barta screamed, bragging that he had recorded a song with Tan Mom as if he was Mariah Carey and Tan Mom was his Nicki Minaj.
Barta and Sydney share the same manager, Gina Rodriguez, who specializes in keeping D-listers like them famous for more than 15 minutes. That night, Gina was booking Sydney on a talk show for while she’s in New York. The talk show would pay Sydney to stand on a stage and argue with one of her friends who disliked the plastic surgery she’s received since she outed Weiner. None of Sydney’s friends hate her surgery, so she needed to find someone to pose as her friend. CrackDoubt volunteered to tell Sydney she looked like shit.
Sydney understood what was going on. Throughout her stay in New York, she openly discussed how she has experienced poverty. “We were never so poor that we were like homeless of anything, but my mom certainly had a lot of relationships when I was younger, and we moved around a bit, and my dad worked really hard but made less than $35,000 a year,” she said.
At the Outback, she said she only takes these gigs because they’re the only work someone will give a girl who is dealing with something much bigger than a scarlet letter—a scarlet jarred labia.
The next morning, Sydney woke up and walked out onto my balcony to smoke a cigarette. Looking at her unkempt face shocked me. Even in the age of TMZ, we rarely see celebrities, whether they’re Jennifer Lawrence or Octomom, without makeup on.
“I have a sex tape, but I don’t like people knowing I smoke cigarettes,” she groaned when she saw me taking notes about her cigarettes.
Before Sydney put her face on, she wanted to paint my nails and play dress-up with the pigeon and horse masks she traveled with. She grabbed my hand and started to apply confetti-colored nail polish to my nail.
She threw this see-through mask at me and then told me she had given me “disco nails.”
As Syndey prepared to get dressed for a guest appearance on VH1, she received a call from Gina Rodriguez. The talk show passed on CrackDoubt, but were willing to use Barta’s friend who Sydney had never met. Immediately Sydney started hypothesizing ways to make their friendship appear legitimate. “We can tell him we’ve known each other for two years,” Sydney told Gina. “We met through Brian, although I don’t know who Brian is.”
Sydney had little time to get dressed and make her VH1 show and sighed as she quickly attached her fake eyelashes to her face. “You’re lucky you don’t have to wear fake eye lashes, Mitchell. You're just a pretty little cunt,” she said. “The most important thing I learned this year was how to put on fake eyelashes.” She failed to realize that she didn't need them.
Sydney doesn’t glow like an A-list celebrity like Marilyn Monroe, but she does emits the same charisma as Joyce McKinney, the subject of Errol Morris’s Tabloid who became a British media fixture in 1977 when authorities accused her of kidnapping a Mormon.
“I have qualities about me that are really immature and silly but also I have a depth to me,” she said. In her hometown, everyone always said she would become famous, which makes sense considering her name is Sydney Leathers, but Sydney never thought it would turn out this way: “Now all the people from my hometown who thought they ‘deserved’ to be famous totally hate me, and it’s hilarious.”
She comes across as defiant when she says statements like this, but as I spent more time with her, I realized that her neighbors and commenters’ negative statements about her cause her harm. As we walked to Times Square for her VH1 appearance, she worried about being recognized. I thought she was paranoid, but then I saw a creepy man walk past her and whisper, “Sydney.”
Sydney credits her current predicament to three Buzzfeed reporters: Andrew Kaczynski, Ellie Hall, and Michael Rusch. Although Sydney anonymously leaked Weiner’s messages to The Dirty, she intended to stay anonymous. But, a year ago this week, Sydney received a Facebook message from a stranger with a mysterious that included a link to a listicle the three reporters wrote.
“You're going to be famous,” the message said.
The listicle outed Sydney as Weiner's digital mistress. That week, Sydney broke down and contemplated suicide. Sydney didn't want fame; she simply wanted to stop Weiner from winning the election because she thought if he was lying about sexting, he probably was making other false statements. She wanted to work in politics to help people, and that was now impossible. As reporters swarmed her apartment, she broke down and contemplated suicide.
“I like Ted Kaczynski more than Andrew Kaczynski,” Sydney told me later as she lay on a blow-up mattress on my floor. “I believe he has more of a heart and soul, and he’s the fucking Unibomber.”
At the same time, Sydney admitted that none of this would have happened if she had never leaked Weiner's messages in the first place. She's someone with bad luck who has also made terrible decisions, and she seemed to regret exposing Weiner. She started to scream at one point when she talked about how Weiner has been able to continue living his life, as she has to suffer from the mistress stigma, yet she doesn't hate Weiner.
“I think we both are [troubled],” she said. “I think that’s why we got along—we have similar impulse control issues for one thing.”
Sydney has managed to find humor in her situation. She joked about how her last phone conversation with Weiner was about House of Cards, and after we walked away from the creepy man in Times Square, she posed for dirty, on-brand photos with a street performer dressed as Elmo.
The performer started to get touchy, so Sydney sprinted across the sidewalk to Toys R Us.
“All Elmos are a little rapey,” she said.
Afterwards she approached a man dressed as Toy Story's Woody and asked him to pose in a dirty photo with her, but he refused to touch her. “You need to act like you are fucking my ass!” Sydney screamed at him.
I told Sydney how Woody and Elmo probably can't find other jobs.
Sydney laughed. “Welcome to my world!”
The one plus about Weinergate is that Sydney has been able to receive all the cosmetic work a girl could dream about. After her VH1 appearance, I followed her to Dr. Richard Westreich's office on the Upper East Side, where Sydney received botox injections.
”I don’t want to look like a Real Housewife,'” she told the doctor.
Sydney occasionally expresses shame about who Weinergate forced her to become since she once aspired to work in politics, but in many ways she has skills and opportunities the rest of us may never have. When we weren't running to talk shows, doctor's offices, or events at Sarah Lawrence, Sydney and I sat on beds in my room talking about sex and pop culture.
I told Sydney that I had struggled to meet guys after I was sexually assaulted a few years ago. I knew how to write about sex, but I wasn't very good at meeting dudes. Sydney grabbed my phone and started to rebrand my Grindr. First, she strolled through my Facebook pics to choose a new default photo for me.
Then she had me pose for pics to send to guys.
And finally, Sydney taught me how to sext. “Tell him, ‘Hey sexy,’” she said. I sent the pick-up line to every guy on Grindr I found sexually attractive. Within a few hours, I had received at least ten dick pics. By 11 PM, I was sucking a 26-year-old Columbia graduate student's cock.
When Sydney lived with me, I felt powerful, the same way PCP addicts feel when they do drugs and jump off buildings. I could have sex. I could make offensive jokes. I could do what I want, and nobody would care. For the first time in a long time since I stopped talking to most of my family, I felt at peace.
When other people are around Sydney—from CrackDoubt to Amy, the photographer who shot these photos—they said they felt the same way. Sydney understands their feeling: “I thought I wanted this very structured, almost corporate work life,” she said, “and then all of this happened, fucking throwing everything for a loop. I think there are people that get stuck in that corporate world, who can’t fully express themselves, whether it’s just through humor or sexuality, whatever it may be. I have this platform where I can say whatever the fuck I want and don’t have repercussions really.”
Weinergate has freed Sydney in many ways—but this is still America, where nothing is free, and Sydney has paid a price for this freedom. Where most people’s family members only had to worry about their phones blowing up with work emails, Sydney had to deal with guys tweeting unsolicited dick pics at her during my graduation. After Barbara Walters appeared on stage to donate her archives to Sarah Lawrence, Sydney seemed depressed.
Sydney smiled in photos with me as she wore a pink and gold dress—the same dress Farrah Abraham wore when I interviewed her for VICE—but I could tell she was down. When we arrived back at my place, I asked her what was up. She said she was unsure if she could ever go back to college to finish her degree. She could probably land an interview with a Walters-like TV host, but she doubted she'd ever graduate.
Last summer, before Buzzfeed outed her, she was working on finishing her degree. If she went back to college, could she fit it in? Would people stare at her. Could she survive? I told her I wasn’t sure, but I knew she was smart enough to graduate at the top of her class.
When I arrived home from work the next day, I found a labia-less mattress on my floor. Sydney was gone. I only spent a week with her, but I missed her. Like Eeyore in Winnie-the-Pooh, she’s a downer, but she brightens up every situation. Her absence made me sad, so I wandered to my bed to lie down. On my pillow, I discovered the masks Sydney and I played dress-up with. I picked it up, and I remembered a short story I read many, many years ago.
Sydney Leathers, I thought, You are a beautiful child.