'The World's Biggest Terrorist Has a Pikachu Bedspread'

Not every leaker is an ideological combatant like Edward
Snowden and Chelsea Manning. Reality Winner may be the
unlikeliest of all.
By Kerry Howley
Illustration by Mike McQuade
December 22, 2017 7:24 am

Reality Winner grew up in a carefully kept manufactured home
on the edge of a cattle farm 100 miles north of the Mexican
border in a majority-Latino town where her mother, Billie,
still lives. From the back porch, a carpet of green meets
the horizon, and when a neighbor shoots a gun for target
practice, a half-dozen local dogs run under the trailer to
hide. Billie worked for Child Protective Services, and in
Ricardo, Texas, the steady income made her daughters feel
well-off; the fact that they had a dishwasher seemed
evidence of elevated social standing. Billie, a chatty
redhead with the high-pitched voice of a doll, supported the
family while her husband, Ronald, she says, "collected
degrees." It was Ronald who named Reality. The deal had been
that Billie got to name their first -- Brittany -- but their
second was his to choose. He noticed, on a T-shirt at their
Lamaze class, the words I COACHED A REAL WINNER. He wanted a
success story and felt that an aspirational name would
increase his chances of producing one. Billie did not
object; a deal is a deal.

Ronald was intellectually engaged, though never, during his
marriage, employed, and Reality's parents separated in 1999,
when she was 8. Two years later, when the Towers fell,
Ronald held long, intense conversations about geopolitics
with his daughters. He was careful to distinguish for them
the religion of Islam from the ideologies that fueled
terrorism. "I learned," says Reality, "that the fastest
route to conflict resolution is understanding." She credits
her father with her interest in Arabic, which she began
studying seriously, outside school and of her own accord, at
17. It was this interest in languages that eventually drew
her into a security state, unimaginable before 9/11, that
she chose to betray. Fifteen years after those first
conversations with her father, Reality's interest in Arabic
would be turned against her in a Georgia courtroom, taken as
evidence that she sympathized with the nation's most feared
enemies.

Reality was an almost comically mature adolescent,
intellectually adept, impatient with her peers, with a
compulsive drive to improve herself she would eventually
channel into an obsession with nutrition and exercise. Her
body was strong and substantial and unadorned: thin blonde
hair tied up, no makeup, clothes that suggested a lack of
interest in the act of dressing. She was shy and shyly
mischievous. In the eighth grade, she organized a food fight
so intense that she was banned from walking during
graduation, though her mother points out that she was
careful not to schedule it during spaghetti day, when it
would have been especially messy.

Reality agreed to date her high-school boyfriend, Carlos, on
certain conditions intended to improve and to edify. Carlos,
who was failing out of school and broke, had to read a
particular number of books a week. He had to maintain at
least a C average. He had to get a job. He did not have
clothes suitable for employment, but Reality would work on
that; she had her mother take Carlos shopping for khakis and
a polo. "Reality takes in a lot of strays," says her mother
with a sigh, "and I don't mean just animals."

She was a talented, stylish painter, and her most frequent
subjects were herself, Nelson Mandela, and Jesus. She was an
inveterate smasher of phones. She threw one across the room
while talking to her father, who struggled with an addiction
to painkillers and who she sensed was stoned, and cracked
another one falling from a tree she'd climbed in a fit of
whimsy. A third phone met its fate when it simply wasn't
working. "How hard is it to be a phone?" she yelled, threw
it, smashed it.

Reality was raised six miles from a naval base, in a
household where humanitarian and military motives were not
taken to be in tension, at a moment, just after 9/11, when
the country had mostly unambivalent feelings about the moral
might of its armed forces. "What could be more
humanitarian," Billie asks, "than protecting your country
and innocent victims of war and terrorism?" As an
adolescent, Billie had dreamed of joining the Air Force
herself but ended up advocating for abused and neglected
children as a social worker. During Reality's senior year,
an Army recruiter came to her high school and zeroed in on
her as a smart, athletic potential recruit. He took her out
to lunch at a Kingsville Whataburger multiple times a week,
for several weeks, until she agreed to take an assessment
test.

No one was surprised when Reality's sister, Brittany, went
on to college, absurd amounts of college, such that she
walked out of Michigan State with a Ph.D. in pharmacology
and toxicology last year. But Reality had then, and has now,
a skepticism of academic degrees, which she recently
described to me as "hundred-thousand-dollar pieces of paper
that say you've never had a job." ("It's interesting," her
mother notes, "because of her father?") She wanted her life
to start. She wanted to make the biggest difference she
could, as soon as she could. It wasn't until she was getting
on the bus for basic training that she told her mother she'd
applied to engineering school at Texas A&MKingsville,
received a full scholarship, and turned it down.

Based on her test scores, Reality was selected to be a
cryptolinguist, which is to say she was tapped to help the
military eavesdrop on people speaking languages other than
English. She wanted Arabic, but the ones assigned to her
were Dari and Farsi -- languages of use to a military
vacuuming up conversations from Afghanistan and Iran. She
would spend two years becoming fluent and another year in
intelligence training before she was sent to Maryland's Fort
Meade. Along the way, she'd be one of a few students
admitted to a selective program in Pashto, yet another
language in which she would become fluent.

In Maryland, her life, according to those closest to her,
involved an exceptionally punishing exercise regimen,
volunteer work, and 12-hour shifts listening to the private
conversations of men and women thousands of miles away.
There was also anxiety. Reality worried about global
warming. She worried about Syrian children. She worried
about famine and poverty all over the globe. Highly critical
of her carbon-spewing, famine-ignoring fellow citizens, she
nevertheless thought her humanitarian impulses were
compatible with the military's mission, and wished her
fellow Airmen were not just more competent in their jobs but
more motivated to do them well, to save the vulnerable from
acts of terror.

To those around her, Reality was a never-ending, frequently
exhausting source of information on the world, its problems,
and our collective obligation to pay attention. She gave her
sister a marked-up copy of the Koran, rife with Post-it
notes, and told her to read it. With an organization called
Athletes Serving Athletes, she pushed wheelchair-bound kids
through half-marathons. ("Athletes Serving Athletes," said
her ex-boyfriend Matt Boyle. "She'd never shut up about
that.") She donated money to the White Helmets, a group of
volunteers performing search-and-rescue missions deep in
rebel-held Syria. She told those around her to watch 13th, a
documentary about racial injustice in the prison system.

On Facebook, where she called herself Reezle Winner because
the site had rejected her legal name, she friended her yoga
instructor, Keith Golden. "I was like, Who the fuck is
Reezle?" said Golden. Thereafter he called her "Diesel
Reezle." He had, as everyone around Reality did, the sense
that she was an extremely competent linguist. "I'd say, 'I
bet you dominate that military shit, they fucking love you,
don't they?' And she'd say, 'Well, yeah, I'm good at my
job.' "

What remained abstract and distant to the news-consuming
public was neither abstract nor distant to Reality. "She was
really, really passionate about Afghanistan and stopping
ISIS," says Golden. "We would go to lunch, and that's pretty
much all she would talk about. She was despondent that ISIS
was the way that it was, that we can't do anything to help
the whole situation, that it's so fucked up."

The people closest to her did not know precisely what Airman
Reality L. Winner did during her 12-hour shifts at Fort
Meade. They only knew that there were certain days when she
knew something big was coming and went to bed early. Reality
told her mother that she might have PTSD. If she were to
explain the nature of her work stress to a therapist, she
would risk being charged with espionage. She exercised, and
she journaled. She kept thick diaries full of small text,
Post-it notes scrawled to the margins. She wrote down
instructions, inspirational quotes, arguments she was having
with herself. A couple of times a week, for hours at a time,
she would talk to her father, whose health was failing but
who was constantly watching the news. They discussed current
events of concern to her, like the war in Syria.