Chelsea Manning Changed the Course of History. Now She’s Focusing on Herself

chelsea manning vogue september 2017
New Wave “It’s not like I’m living in fear or anything,” Manning says. “I’m so glad to be out and about and walking around.” Here, Manning in a Norma Kamali swimsuit.Photographed by Annie Leibovitz, Vogue, September 2017

One hot, humid early-summer evening in New York, a hired car slows on Bleecker Street, and a young woman inside prepares for her first party out in years. She is wearing a midnight-colored semiformal dress by Altuzarra and Everlane ankle boots with heels. Her hair is trimmed into a pixie cut; her makeup softens, but won’t hide, a dust of freckles. “I don’t know if I’ll know anybody,” she fretted earlier, but she seems to have quelled what nerves remain. She is accompanied by a couple of men who surround her like guards. For the first time in a long time, that’s a welcome thing.

Chelsea Manning—graceful, blue-eyed, trans—smiles and prepares herself. Since her release from the Fort Leavenworth prison, on May 17, Manning has been living in New York, with a low profile. Tonight she will make her social debut in her own skin. From February to April 2010, while living as Bradley, an Army intelligence analyst stationed in Iraq, Manning sent three-quarters of a million classified or sensitive documents to WikiLeaks. The breach’s breadth was startling, as were its contents, ranging from the so-called Collateral Murder video, showing a U.S. helicopter killing a group of Baghdad pedestrians that included children and press, to hundreds of thousands of “Cablegate” documents, disclosing 44 years of State Department messaging. When Manning’s role became clear, she turned into a polarizing figure—celebrated as a whistle-blower by some, condemned as a traitor by others. In August 2013, after pleading guilty to ten charges and being found guilty of 20, she was sentenced to 35 years in prison. The day after the sentencing, Manning came out publicly as trans.

Tonight, a summer Monday, is a different kind of coming-out. To honor the occasion, she has picked an event with a celebratory turn: the after-party for the Lambda Literary Awards, which each year honor books by members of the LGBTQ community. The evening is glamorous; the guest list is varied. Here Manning will reintroduce herself to a community in which she seeks acceptance for more than her heavy past.

The car stops in front of Le Poisson Rouge, a Washington Square art space. “I’m not sure how to do this,” Chase Strangio, an ACLU lawyer, murmurs in the front seat. A gregarious young man with a trim Clark Gable mustache, Strangio has emerged as one of the nation’s leading trans-rights lawyers, helping represent Gavin Grimm, the trans student in Virginia who challenged his exclusion from the boys’ bathroom at his high school, and successfully advocating for Manning’s hormone therapy in prison. With Manning now out in the world, however, he faces a new challenge: remaining alert to unwelcome attention.

“I think that looks pretty discreet,” Tim Travers Hawkins, a filmmaker who’s making a documentary on Manning, says, judging the entry. When his project, executive-produced by Laura Poitras, started two years back, he intended to use Manning’s prison diaries to shape a documentary with an invisible hero. Then, in the final days of his term, President Obama commuted Manning’s sentence. “It was kind of unbelievable,” Poitras says. “All the news had been so, so bad.” For Hawkins, Manning’s release introduced new imperatives. “It was a radical shift in the way the film existed,” Hawkins says. Tonight, he’s brought a compact camera along.

Manning, Strangio, and Hawkins clamber rapidly inside. A Lambda host guides Manning down a flight of steps. The party is just starting. At one end of the space, a platform, slightly raised above the dance floor, is marked off with velvet rope. A plate of crudités awaits; Manning orders a gimlet. She’s extroverted, she says: “I love being around people.” While living as a man, she often went to clubs and parties, even in stodgy Washington, D.C. “People are a lot more open and outgoing in New York,” Manning explains. “In D.C., you really had to, like, know someone.”

Music pounds through the room, which is dim and bathed in blue and fuchsia light. As the space fills, a few brave souls approach Manning, then a few more. Soon the platform is packed with people hoping to take a flash-bleached selfie.

“I just wanted to say hello. You’re, like, a perfect hero.”

“I’m going to give you this card. We’d love to throw a party for your return.”

Manning seems startled by the attention. “Thank you!” she keeps saying. She is 29 now, with a confidence that, even in a novel city, hits like sunlight at high altitude. Though she’s petite—just a few inches over five feet—she speaks with a clarion directness, as if constantly projecting toward an unseen back row. In prison, she read the fashion press (“I missed seven years of fashion, but I went through every season in a magazine!”), and while she’s embraced her femininity, she eschews what she calls “fertility style”—“bunnies and hearts and stuff”—for more current, gender-neutral garments. While serving out her sentence, she got her hands on photos from Barneys’ 2014 trans campaign, shot by Bruce Weber. “That was a really important thing for me to see,” she says.

From the stage, the DJ mixes sharpen: “Uptown Funk,” “I Feel It Coming.” But there isn’t time to dance. She’s standing, greeting new faces from all sides, thanking, thanking some more. Her left arm is crossed over her belly, cradling her opposite elbow, which is straight. When Beyoncé’s “Love on Top” begins its climbing modulations, she uncrosses her arms and begins fidgeting—mindlessly, flirtatiously—with the charm on her gold necklace, drawing it back and forth between her thumb and forefinger. She sways. She lets herself lean forward, laughing at a joke. When her newest friend wanders away, she turns around and smiles.

“I’m starting to loosen up!” she says.

When Manning was growing up in Crescent, a town of some 1,400 north of Oklahoma City, she struggled to pinpoint a reason she felt so awkward. “I knew that I was different,” she says. “I gravitated more toward playing house, but the teachers were always pushing me toward playing the more competitive games with the boys.” She recalls, “I spent so much time wondering, What’s wrong with me? Why can’t I fit in?” Sometimes she felt left behind; at other times, she leaped out in front. Once, she and a group of other kids were allowed to take a field trip to Frontier City, an amusement park known for its loopy, soaring Silver Bullet roller coaster. Other students were petrified. Manning couldn’t wait to get on and boarded the ride all alone: “I’m a bit of an adrenaline junkie, I think it’s safe to say.”

It’s a June afternoon, and we are sitting in a park along the Hudson River, a short walk from the sleek Tribeca building where Manning has been living since arriving in New York. Today she is dressed with a mixture of straightforward elegance and function: a casual black sleeveless Marc Jacobs dress with playful paisley lining, a small purse from The Row, Borderline boots by Vetements x Dr. Martens, and—the cinching touch—a black utility belt from 5.11 Tactical, a gear company that supplies law enforcement and the military. “I’ve been a huge fan of Marc Jacobs for many, many years, even going back to when I was wearing men’s clothing,” she explains. “He captures a kind of simplicity and a kind of beauty that I like—projecting strength through femininity.”

In Manning’s telling, strength was a necessity before it was a choice. When she was eleven, her father, a computer engineer who’d gotten his start in the Navy, announced that he was moving out, effectively ending his marriage. That night, her mother swallowed a bottle of pills, then told Chelsea’s older sister, Casey, what she’d done. On the hurried drive to emergency room, the journalist Denver Nicks reports in Private, his book on Manning’s early life, it was Chelsea’s job to sit with her mother in the backseat and make sure that she did not stop breathing.

Over the months that followed, Casey and Chelsea, then still known as Bradley, struggled to manage their mother’s alcoholism while also learning to navigate basic domestic chores. Nicks reports that their mother, who’d grown up in Wales and married early, didn’t know how to write a check, let alone pay bills or seek alimony. “I had to learn how to do all of this stuff with my mother and also deal with the friction between my parents,” says Manning. “I loved them both, but they were angry at each other. I always felt like I was doing something wrong and I had caused it.” (Manning’s family members have declined interviews since her release.)

From twelve to thirteen, Manning grew up quickly. She realized that she was attracted to boys, and considered herself gay. Her father had introduced Manning to computers and programming at a young age, and Manning began to see the Internet—vast, anonymous, and full of answers—as an escape. “I learned that I wasn’t alone. I learned about all these different life possibilities and options,” she explains. She began to find her first natural identity. “Because I would actually be anonymous online, I could be more myself.”

The Web also held constant through a series of displacements. In November 2001, when Manning was just shy of fourteen, her mother decided to return to Wales and took Manning with her. (Casey had moved away; their father had remarried.) Her responsibilities increased as her mother’s health declined. In 2005, after a fluky brush with the July 7 London bombings—Manning says she was near King’s Cross station at the moment of the Tube explosions—she moved in with her father, his wife, and his stepson. That arrangement didn’t end well: Mounting tension ended with Manning allegedly brandishing a knife and her stepmother calling 911. Manning lived for a spell with a friend in Tulsa, then drifted to Chicago. In increasingly dire straits, she was taken in by her aunt Debbie, in suburban Maryland. She worked at Starbucks and Abercrombie & Fitch; she explored the LGBTQ scene of greater D.C.; she enrolled, briefly, in community college. At nineteen, she started seeing a psychologist for the first time.

“That’s the part of my life I replay the most: whether or not, living in Maryland and seeing a therapist, I could have finally been able to say, ‘This is who I am; this is what I want to do.’ It was the first time in my life when I really considered transitioning. But I got scared,” she tells me. “I really regret the fact that I didn’t know or realize I already had the love I needed, especially from my aunt and sister—just to seek support.”

Rather, she made a defiantly different choice. It was the moment of the so-called surge in Iraq. The news on TV was grim. “I don’t know who I am,” she recalls in the park. “Maybe the military will allow me to figure that out.” She looks out toward the river. “It was a naive thought, but it was very real to me in 2007.”

On the grass behind us, teenage girls are putting together a dance routine: “Five, six, seven, eight!” Not far away, upriver, are the piers where, for years, LGBTQ teens have congregated at the witching hour to vogue under the stars. If Manning had remained in Maryland and been a little braver, she now believes, her 20s could have been quite different.

Instead, she traveled as a new Army enlistee to Fort Leonard Wood, in Missouri; trained as an intelligence analyst at Fort Huachuca, in Arizona; and worked for about a year at Fort Drum, in New York, as an analyst with a top-secret clearance. In October 2009, she was shipped to a base outside Baghdad, where she became Specialist Manning: an anguished 22-year-old in a harsh environment, with access to some of the military’s darkest secrets.

The clock has barely struck midnight at Le Poisson Rouge when Manning’s first night at the ball seems to end. The music stops; fluorescent lights flicker on overhead. There will be a small after-after-party—a loose, laid-back affair—at Julius, a tavern in the Village that is sometimes called the oldest extant gay bar in New York. Strangio has peeled off—he has a family to return to—but Manning decides to continue: The world is new again, and she’s not ready to go home.

About a dozen people walk the half-mile to the tavern. It is 12:45 a.m. and quiet on the streets; sprinklers stutter softly over the Minetta Green. Manning has no I.D. yet, for arcane reasons—she lost her old one with her old life—but the doorman at Julius is expecting her. For weeks after coming to New York, she wandered all around the city, unrecognized. “It’s not like I’m living in fear or anything,” she tells me. “I’m so glad to be out and about and walking around.”

Julius’s interior creaks with landmark artifacts: black-and-white photos checkering the walls, posters commemorating the gay-rights Mattachine Society’s 1966 “sip-in” at the bar. Manning alights on a bench underneath an American flag whose stripes are replaced with the bars of the pride banner. Conversation foams around her while the jukebox plays. They are deep into drinks; people are sitting on laps. Manning falls into conversation with January Hunt, a writer, musician, and artist who is also a young trans woman. Manning is describing her trip into Brooklyn for a tech “meet-up” in a derelict building; it struck her, she explains, as “very New York.”

Manning publicly came out in a written statement, sent to and read aloud on the Today show, in which she asked to be called by female pronouns and expressed interest in hormone therapy. She had thought of making an announcement earlier, she says—she had taken her first outing in women’s dress in February 2010 and had told guards at the detention center where she was first imprisoned that she was a woman—but had been advised that it would complicate the trial. “The opportunity to do it on the Today show popped up, so it happened a little bit sooner and a little faster than I hoped it would,” she told me. Still, she says, she was taken aback by the response. “I was honestly a bit surprised by the outpouring of love and support that I got,” she says. If there was backlash, too (and there was), she doesn’t seem to have registered it—a tellingly upbeat response from a woman who now sprinkles her tweets with hearts and rainbows.

Prison bureaucracy was another story. Almost immediately after coming to the ACLU in 2013, Strangio—a trans man himself—began work on Manning’s civil case, fighting for her to begin receiving hormone therapy. “Our goal was to get her the health care that she needed,” he explained. “Even when there are legal principles that are pretty unambiguously on our side, there’s so much cultural bias we’re confronting in the courts and in other systems.” Meanwhile, behind bars, Manning sought equilibrium in other ways. “The first thing I learned to do was avoid television,” she says. She took out subscriptions to “50 or 60” periodicals, she says—news and global-affairs publications, science magazines, technical journals, and, of course, fashion glossies. She describes it to me as “like having a printed version of the Internet.” And she read books: literary classics, fantasy series, contemporary histories. She liked biographies: Queen Isabella, Joan of Arc. She read Cheryl Strayed’s memoir, Wild, three times. Many of Manning’s favorites seemed to emphasize personal strength or bureaucratic disaffection. She read Catch-22, she says, more than once. “I was institutionalized to such a point where my expectations were limited to, I’m going to eat the next meal. I’m going to go to sleep. I’m going to be here the next day,” Manning says. Before commutation, this outlook had psychological costs; as recently as last October, she tried to kill herself for the second time. Then, in January 2017, the White House phoned the office of one of her lawyers.

In his statement announcing the commutation, President Obama emphasized that it was not a pardon for her crime. “Let’s be clear: Chelsea Manning has served a tough prison sentence,” he said in a press conference. “I feel very comfortable that justice has been served.”

On the day of Manning’s release, things happened quickly. She picked her first outfit for life as a woman: a black-and-white striped blouse, with matching sneakers. She stopped at a roadside pizza joint, got a pepperoni slice, and posted a photo of it to Instagram. (“Freest pizza ever!” she tells me.) She had the lawyers who picked her up drive her to the countryside. “I think I spent, like, five or six hours sitting outside.”

A day after leaving Fort Leavenworth, she posted a new photo (“OK, so here I am everyone!!”) with the coder-inspired hashtag #HelloWorld. She had on a trim black dress by one of her favorite designers, Gabriela Hearst. Her hair was crisply coiffed; she wore a vibrant lip. In a Guardian column, written while in prison, Manning had discussed her nervousness about moving through the world as a woman. Now that she’s no longer worried about being “found out” by the military, she says, the fear is gone. “It feels natural. It feels like it’s how it’s supposed to be, instead of this anxiety, this uncertainty, this ball of self-consciousness that comes with pretending to be male,” she says. “It didn’t feel right. I didn’t know what it was. I couldn’t describe it. Now that’s gone.”

Poitras, who met Manning for the first time after her release, says she was startled by the young woman’s focus. “There are people who have really put their lives on the line for something, and they come out on the other side of it. You can feel that with her,” Poitras tells me. “Now that she’s free, what is she going to do with her freedom?” She adds, “When I first met Ed Snowden in Hong Kong, he had the same sort of eerie power.”

Twice during our conversations, and in slightly different ways, I ask Manning what she regrets from the period when she was living as Specialist Bradley Manning. Her leaking of state secrets doesn’t appear on the list, although that decision remains the most publicly controversial of her life, earning her accusations of treason and reckless endangerment. “I’ve accepted responsibility for my own decisions and my own actions,” she says. When we speak, Reality Winner, the 25-year-old intelligence contractor, has recently been arrested on suspicion of leaking information about Russian hacking in the 2016 U.S. election, adding to a list of leakers who, like Snowden, have become household names. Manning tells me that she has nothing to say about Winner (“All I know is what I see in the media reports”) but speaks about what she refers to as “the larger issue.” “I think it’s important to remember that when somebody sees government wrongdoing—whether it’s illegal or immoral or unethical—there isn’t the means available to do something about it,” she says. “Everyone keeps saying, You should have gone through the proper channels! But the proper channels don’t work.”

Manning describes trying to release information to the press before WikiLeaks. “In 2010, I was literally scrambling around D.C. trying to get The Washington Post to publish this stuff, and then I went to The New York Times.” Manning has said that a reporter at the Post with whom she spoke briefly over the phone wouldn’t commit to a story, which she took as a sign of uninterest. At the Times, she says, she left a message on the voice mail of the ombudsman, confusingly called the Public Editor. The editor and his assistant later said that they had no memory of such a message, but explained that they received hundreds a week. “I did this all on leave,” Manning says. “I had only twelve days.” The approaching “Snowmageddon” made it harder still. Manning traveled from public phone to public phone, to avoid a traceable line. “I ran out of time,” she says. Before returning to Iraq, she sent files to WikiLeaks.

Even so, Manning continues to take her struggle to find an outlet as proof of a systemic problem. “We need to have more ways to talk about what’s going on in government,” she says. I ask what those ways might look like. “I don’t know what’s right,” she says. “I have certain values. I live by those.”

When it comes to information freedom, those values remain controversial. Many lawmakers bridled at her abbreviated sentence; at the time of the commutation, Paul Ryan said, “Chelsea Manning’s treachery put American lives at risk and exposed some of our nation’s most sensitive secrets.” Others argue that her motives, like a public-interest journalist’s, were honorable—or that the actual damage of the leaks was small. Beyond some vocal LGBTQ advocacy (she was a star of the summer’s Pride March in New York, waving from a drop-top Nissan alongside Gavin Grimm), Manning herself has mostly stayed circumspect on issues of politics. Still, in a Guardian column from January 25, a few days following her commutation, she offered a soft criticism of President Obama’s tactical approach: “The one simple lesson to draw from President Obama’s legacy: Do not start off with a compromise. They won’t meet you in the middle.” President Trump, newly elected, lambasted Manning over Twitter: “Ungrateful TRAITOR Chelsea Manning, who should never have been released from prison, is now calling President Obama a weak leader. Terrible!”

Manning has avoided a rejoinder to the president’s tweet. And to the extent that WikiLeaks of 2017 (which seems to have pursued specific electoral outcomes in France and America and is dogged by the troubled reputation of its leader, Julian Assange) has a different public reputation than the 2010 organization (which claimed more categorical anti-secrecy principles), she has avoided opinions there, too. “I’ve been in prison for seven years! I’ve been completely disconnected from all of that,” she tells me. Her plan is to live in New York until late summer, then move to suburban Maryland, not far from where she was before.

By then, she hopes to be acclimated to a new life. For the moment, certain habits of this decade strike her as weird. Our phone fixation, for example. “We’re sitting in the same room as each other but looking at our phones constantly,” she says. “Before I was in prison, I was one of the only people on social media. I was a novelty. Now everybody’s on social media all the time!” It’s too much. “I think that’s where a lot of this miscommunication, polarization, friction, and chaos is coming from.”

Thus, though she tweets and Instagrams, Manning has tried to focus on more in-the-moment pursuits. She still loves video games, though she has forsworn the violent ones. Soon after leaving prison, she began teaching herself the programming language Rust. (“It has a lot of features that weren’t available seven years ago,” she says.) She hopes to begin dating—“I’m not planning to be single!”—but intends to wait until her life settles, in Maryland.

She is also at work on a memoir. “I’m trying to tell the story as if it was happening now and you’re with me,” she explains. Hawkins, the documentarian, says he plans to stop shooting soon, as Manning’s personal narrative finds its own way in the world: “She’s too young for this film to attempt to be the definitive story of her life.”

Manning does not know what her career will be. While living as Bradley Manning, she expressed an interest in running for political office. I ask whether that’s still on her mind. “I’m certainly not going to say no, and I’m certainly not going to say yes,” she says. “My goal is to use these next six months to figure out where I want to go.

“I have these values that I can connect with: responsibility, compassion,” she goes on. “Those are really foundational for me. Do and say and be who you are because, no matter what happens, you are loved unconditionally.” It’s the lesson, she says, that she wishes she learned earlier. “Unconditional love,” she says. “It is OK to be who I am.”

In front of an apartment building in the East Seventies, near Central Park, Manning meets up with Strangio to pay a visit to a hero of New York’s LGBTQ past. It’s 90 degrees, clear, and sticky. Manning arrives late, looking addled and a little faint. She had a subway snafu, she explains, and then a long walk. Strangio takes her shoulders and gives them a shake. “Oh, my God—hi!” he says with get-ahold-of-yourself astringency. Inside, they board a tiny elevator that seems as old as the building.

“Everybody in!” Strangio says merrily as it begins groaning upward. “We’ll just get stuck in here a few days.”

“I’ve got a flashlight,” Manning deadpans.

At a time when drag queens were widely shunned, Jack Doroshow, better known as Flawless Sabrina, blazed a trail across Philadelphia and New York with her high-profile drag pageants, forcing the cities to acknowledge and accept their androgyne and transgender communities. Bobby Kennedy helped her book a venue. Andy Warhol helped secure funding for a film on the pageants, The Queen (1968), which went to Cannes. Flawless posed for Diane Arbus, acted for John Waters, and dated William S. Burroughs. Along the way, she was arrested several times and came to be known as a “mother” figure in the queer community. Now in her late 70s, she suffers from various age-related ailments. There are good days and bad days, but today is good.

The long wall of Flawless’s sitting room is mirrored, floor to ceiling. A desk near the window supports pineapple-esque lamps and on the far wall is a framed canvas that looks like—is assumed to be—a late-period Picasso. Scattered through the room are heads: mannequin heads, papier-mâché heads, other heads, one sporting a costume-ball mask and feather headpiece, another wearing a wig and sunglasses, a third stabbed at the scalp with hypodermic syringes.

Just then, Flawless enters the room. “Gorgeous!” she says, looking at Manning. “Girl, that’s what I’m talking about.”

She is sitting in a wheelchair pushed by Curtis Carman, an artist who is Flawless’s partner. She looks old, alert, and not unlike Picasso herself: bald, with a striped shirt and a big, knitted navy cardigan. Carman helps her climb into a thronelike chair behind the desk. “Now, how’s your family?” she asks Manning.

“They’re all right,” she says. “They’re laying low a little bit.” She hasn’t seen her mother yet, Manning explains. She lives in the care of her family and cannot travel.

“But you’ll do that,” Flawless says. It’s not a question. “You’re young, aren’t you?”

“Twenty-nine. I hope that’s young.”

“You bet.” Flawless allows herself a smile. “I mean, as I look at it, everybody’s pretty new.”

Flawless brings her palms together. “All I see is a very natural, very beautiful little girl,” she says. “The only jarring thing is that there’s so much power. This is somebody who has changed history.”

Manning thanks her and keeps talking—about her move to Maryland, and then about her writing. Flawless starts shaking her head. “I can’t get over how beautiful you are,” she says.

Through the next half-hour, they discuss the military, the Tonys, the past. Before Manning leaves, Flawless is keen to pass on some wisdom. “Think about your story,” she says.

“I’m not done yet!” Manning protests.

“No,” Flawless says slowly.

Strangio says they should let Flawless rest.

“It’s not easy to change the world,” Flawless chirps. She draws Strangio close. “I am so proud of you,” she says, and gives him a tight hug.

Manning comes next. Flawless wraps her aged arms around her small frame. “Thank you so much,” she whispers, so softly that Manning may not hear. “Thank you so much.” When Manning stands, she moves briskly toward the door. Flawless’s eyes are wet with tears.

In this story: Fashion Editor: Phyllis Posnick. Hair: Jimmy Paul for Bumble and Bumble; Makeup: Alice Lane. Tailor: Maria Del Greco for Christy Rilling Studio. Set Design: Mary Howard