"This Navy record says female, but this paper says male," the grim-faced sergeant major noted, displaying two sets of personnel records. "So, what are you?"
After an awkward pause, Wilson, who joined the Navy as a woman but who has long felt like a man, provided the answer that set in motion the end of his military career: "I am male."
More than two years after the repeal of the law that barred gay men and lesbians from serving in the military openly, transgender service members can still be dismissed from the force without question, the result of a decades-old policy that dates back to an era when gender nonconformity was widely seen as a mental illness.
The policy, however, is now coming under scrutiny as service members like Wilson become more visible. Transgender service members are increasingly undergoing procedures to align their bodies more closely with the genders with which they identify. Medical experts, meanwhile, are urging the Defense Department to rescind a policy they view as discriminatory and outdated, noting that some of America's closest allies, including Canada, Britain and Australia, have done so seamlessly.
Although the American Psychiatric Association revised its manual last year to indicate gender nonconformity is "not in itself a mental disorder," the Defense Department relies on guidelines that describe transgender individuals as sexual deviants, and their condition as a "paraphilia." Thousands of transgender men and women are now serving in the military while remaining in the closet, according to studies.
"It is a terrible tragedy our people are facing in our great country for no other reason than the fact that they want to express their gender," said Joycelyn Elders, a former U.S. surgeon general who last year co-chaired a study that recommended the military lift its ban on transgender personnel. "We could find no credible medical reason for why transgender persons should be discharged or not allowed in the service."
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Wilson, 24, was born in Warner Robins, a small city in central Georgia that revolved around the namesake Air Force base. An only child raised by a single mother, he recalls feeling he had been assigned the wrong sex as early as infancy.
"Hey, I'm a boy," he recalls blurting out to his mother as a 4-year-old. "The reaction I got was one that even at that young age made me aware that that was not what you were supposed to feel like. So I suppressed it for as long as I could."
As a teenager, Wilson carried himself as a "masculine female," wearing men's clothes and keeping his hair cropped short. A military career appealed to him for the honor that comes with service. But there was another draw, one that researchers say explains why the percentage of transgender people in the U.S. military is twice as high as it is in the civilian population.
"It comes down to the masculinity of it all," Wilson explained. Men struggling with their temptation to transition to women have told researchers that they see military culture as a barrier to keep them from taking the daunting step. In the reverse scenario, Wilson said, it's an easy environment to fit into. "But I think a lot of people look to the military for a new beginning," he added.
As he enlisted, he was urged to become a cryptologic technician. By Wilson's estimate, the Navy spent at least a half-million dollars getting him the highest-level security clearance in government and training him for an intelligence job that involves intercepting and analyzing communications from foreign governments and extremists.
He developed a reputation as a talented, meticulous, hard-working sailor, said Shayne Allen, a former colleague who was stationed with Wilson at the Navy Information Operations Command in Hawaii.
"Landon was someone who you don't see a lot of in the military these days," Allen said. "He not only checked all the boxes, but went above and beyond."
During his time in Hawaii, Wilson earned several awards and accolades for his work. In a unit of roughly 10,000 sailors, he was recognized as the performer of the quarter in 2012 and the enlisted sailor of the quarter in 2013.