Transgender troops face ‘crushing' decision as Trump ban deadline looms

The Hill

05-06-2025

Transgender active-duty service members must decide whether to leave the military on their own or be forced out by Friday under the 30-day deadline announced last month by Defense Secretary Pete Hegseth, a life-altering decision that those interviewed by The Hill said is nearly impossible to make.
'It's crushing,' said Commander 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 that 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 — including Black, gay or female Americans — 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.'
'I believe this is unlawful, and in the meantime, while I challenge it, I'm going to obey the orders,' she added. 'I'm out-processing; I'm doing all my paperwork; I'm doing everything I'm being told to do, and I'm also challenging it, saying, 'I don't think that this is lawful, courts, please make a verdict on it.' And I will honor whatever they decide.'
Commander Blake Dremann, another plaintiff in Shilling's lawsuit, has also begun the voluntary separation process, though he said it hasn't felt like much of a choice. He requested that his separation start at the end of December, when he will hit 20 years of service and be eligible for regular retirement.
'As far as navigating anything else, it has been really just trying to figure out, 'OK, where do I want to live? What do I want to do? How am I going to handle this?'' said Dremann, a naval supply officer. 'I thought I had another 10 years to figure out what I was going to do afterwards.'
Dremann recently returned to the U.S. from Guam, where he had supervised a team of sailors and junior officers repairing submarines for forward deployment on the USS Frank Cable. The assignment, he said, was part of a milestone tour that would have set him on a path to becoming a Navy captain.
Under the Trump administration's new policy, 'That's been taken away from me,' he said.
A member of the Navy since the early aughts, Dremann served under the Pentagon's longstanding ban on trans service members that was lifted in 2016 under former President Obama, as well as under 'Don't Ask, Don't Tell,' which prevented gays, lesbians and bisexuals from openly serving, Trump's 2017 trans military restrictions and now, the more stringent 2025 ban.
'This is the fourth time the military has had a policy that requires me to leave the service,' he said. 'This will probably be the one that gets me.'
Dremann said he would be open to returning to the Navy once he separates if the Trump administration's policy were reversed in the near future. 'I even took my physical readiness test for the year,' he said.
Others hesitated to say whether they would return.
'Unless there were specific policies put in place to prevent, like, what's going on now from happening in the future, having that being a case where let's say, everyone's offered a way back through the next administration, four to eight years later, you can run into this entire situation again,' said Abi, a member of the Air Force based in Alaska who asked that her last name be withheld over privacy and safety concerns.
Her wife, Elizabeth, said she would be similarly uneasy with Abi someday returning to the military. The Trump administration's policy, she said, had betrayed their trust.
Trump's 2017 policy barring transgender troops from serving made an exception for some who had already started to transition. The latest policy makes no such exception, deeming any service member with a current diagnosis, history or symptoms of gender dysphoria unfit for military service.
'To turn around and say, 'I know we said that you could do that, but now that you have, we are choosing to punish you for it.' It's like, what else could they do that with?' Elizabeth asked.
With just under five years of service, Abi said there is no real incentive to opt for voluntary separation. A Pentagon memo issued in February said some trans service members could receive separation pay at double the rate of those who were involuntarily removed, but eligibility requires at least five years of continuous active-duty service.
For now, Abi and Elizabeth are biding their time. They are looking to relocate, possibly to California, where Elizabeth has family, but cannot make concrete plans — including finding work — until they know when Abi will be discharged.
'It's very scary to be in such an unknown position,' Abi said.
Army Reserve 2nd Lt. Nicolas Talbott said he similarly has no plans to voluntarily separate, a decision that, as a reservist, he must make by July 6.
'Most of the incentives for voluntary separation are geared toward folks who have more time and service than I do,' he said. 'So, for me personally, I'm watching to see if any new guidance or any new policies come out. But really, we're just kind of preparing to see what the involuntary separation process is going to look like.'
'I hate the verbiage being used as voluntary versus involuntary,' he added, 'because this isn't really voluntary for any of us. This is not what we wanted.'
Talbott said he's hopeful the policy will again be blocked in court. Like Shilling, he is the lead plaintiff in a challenge to Trump's executive order.
A district judge sided with Talbott and more than a dozen other plaintiffs in March, blocking the administration from implementing Trump's order, which they said was 'soaked in animus.' An appeals court temporarily halted the order as it weighs whether to grant a longer pause.
'I'm kind of trying to do my best to hold down the fort for everyone,' Talbott said. 'That's what I try to stay focused on. I have a job in the military, I have my civilian job as well, and things need to get done. You know, the world does not revolve around this case; the world does not revolve around me by any shape of the imagination, and I have jobs to do, and I have responsibilities, and that's what I try to stay focused on.'