The 30-day deadline, announced last month by Defense Secretary Pete Hegseth, is a life-altering decision that those interviewed by The Hill said is nearly impossible to make.
"It's crushing," said Cmdr. Emily "Hawking" Shilling, who has served in the Navy for almost two decades. "It's heartbreaking."
A naval aviator with 60 combat missions under her belt, Shilling oversaw a staff of about 200 people before she requested voluntary separation last month and was placed on administrative leave. In her latest fitness report, Shilling's commander described her as an "inspiring leader" with "boundless energy" and "unmatched enthusiasm."
"People excel under Hawking's leadership," they wrote, referring to Shilling by her callsign.
The report and Shilling's own experiences contradict how President Trump and administration officials have sought to frame her and other transgender troops' service.
Trump's Jan. 27 executive order to boot transgender people from the military states they cannot satisfy the "rigorous standards" needed to serve, and that allowing their participation threatens military readiness and unit cohesion, an argument long used to keep marginalized groups from serving.
A 2016 RAND Corp. study commissioned by the Pentagon found that allowing trans people to serve had no negative impact on unit cohesion, operational effectiveness or readiness.
Shilling, who currently serves as president of SPARTA Pride, an advocacy group for transgender service members, said she is complying with the Trump administration's policy despite believing it to be unlawful and challenging it in court. She stressed that her views do not reflect those of the Department of Defense or the Navy.
Shilling's lawsuit, filed in February with six other trans service members, argues that "banning ready, willing, and able service members does not further the objectives of the United States Armed Forces."
A federal judge in Washington state, where the suit was filed, sided with the service members in a March ruling that temporarily blocked the administration from enforcing Trump's order.
But after an emergency application from the Justice Department, the Supreme Court ruled in May that the Trump administration could begin enforcing its ban on trans military service.
"My oath is to the Constitution and to obey all lawful orders," Shilling said in an interview. "The only way that I can challenge whether or not something is lawful is through the courts, and so I actually see this as an extension of my duty, of my oath."
Read the full report at TheHill.com.
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