Spc. Madison “Maddie” Holderegger is a bridge crewmember in the Wyoming Army National Guard.

At 22 years old, she is a business owner, home owner and student at the University of Wyoming.

In 2016, she kayaked 2,106 miles in 53 days from Torrington to New Orleans.

She has twice completed the Bataan Memorial Death March, a 26-mile hike through the New Mexico desert carrying a 35-pound rucksack in less than 14 hours.

Maddie is transgender.

Assigned male gender at birth, Maddie left her birth name, Dan, behind when she started the process of transitioning to female about five months ago.

“I believe I am the first transgender person to come out in the Wyoming Army National Guard,” Maddie said. “But I’m pretty sure I’m not the only trans person currently serving in the state.”

According to the National Center for Transgender Equality, an estimated 15,000 transgender people are currently serving in the United States military.

In June, then-U.S. Secretary of Defense Ashton Carter lifted the ban on transgender people serving openly in the military.

Before the regulation change, Maddie had only come out to a few close friends and her lawyer. She was informed of the military’s new stance on transgender service members through an email while kayaking in Nebraska during her trip to New Orleans.

“I was jumping for joy,” she recalled, wide eyed and smiling. “I’d finally come to terms with myself — that I was going to do it. And the world was like, ‘We’ll let you keep serving and be yourself.’”


Born and raised in Evanston, Maddie never quite felt at ease playing with other boys.

“When boys get into arguments, they fight about it,” she said. “I never felt comfortable with that.”

Although Maddie admitted she occasionally tussled with the boys, she gravitated toward the girls’ circles.

“I hung out with the girls because they thought the same way I did,” she said. “I remember thinking a lot of times as a kid, ‘I don’t understand why I can’t wear women’s clothes. I don’t understand why I can’t have longer hair.’”

Maddie said her mother was strongly opposed to non-straight, non-heterosexual ideologies. She thought members of the LGBT community were the same as child molesters or people who engaged in sexual acts with animals, Maddie said.

The young soldier lowered her head and doubt trickled through her voice. She looked away, but it didn’t hide the pain in her eyes.

“She had no problem voicing those opinions,” Maddie remembered. “So, I learned early on that I had to hide the way I felt. I knew I wouldn’t be accepted if I told her.”

Young, scared and confused, Maddie tried masking her feelings with masculine interests such as camping and muscle cars. She delved into religion and tried to will away the disgust she felt when she looked into the mirror and saw a boy’s body.

“I went through a lot of really religious phases where I tried convincing myself not to feel the way I did,” Maddie said. “That didn’t work — obviously— but it decreased my quality of life.”


As early as 12 years old, Maddie started wearing girl’s clothes in secret. With puberty, body hair sprang up everywhere, and her self-esteem stooped to a new low.

“I had a really bad complex about body hair,” she said. “I have really bad body hair. I am cursed by looking like a … Wookiee.”

Having never felt comfortable removing her shirt, she was now confronted by a new terror — the boy’s locker room. Maddie said her peers quickly picked up on her insecurity.

“I used to get bullied a lot for my body hair, because I had more than others,” she said. “I tried everything I could to get the body hair off. It just felt foreign. It felt wrong. It didn’t belong, which in turn made me feel like I didn’t belong.”

However, she soon made a discovery that brought everything into a new light.

“When I learned about transgender being a thing, it’s like the clouds parted,” Maddie said. “Suddenly, everything made sense.”

After high school, she moved to Laramie to attend UW.

“Once I moved out, it was a big step in the right direction,” she said. “Being able to buy clothes that suited me more, even if I couldn’t wear them out, still made me feel good.”


Despite her newfound freedom, Maddie lived in constant fear of being discovered.

She said she had several “poorly written” excuses to offer anybody who came close to uncovering her secret.

“I actually got caught with women’s clothing by one of my good friends,” Maddie said. “Before I came out to anybody, he just walked into my closet, and I was like, ‘Oh … did I leave anything out?’ And of course, I did.”

Her friend inquired about the women’s clothing in the closet, and Maddie froze.

“I was like ‘Oh, yeah, this girl I met left that, I’ll make sure I get that back to her,’” Maddie said. “It was just the worst excuse I could have possibly come up with. I’m not entirely sure whether he bought it.”

Shortly after moving out to Laramie, Maddie joined the Wyoming Army National Guard. She continued to wrestle with her body image and confusing feelings.

Even when she decided she was ready to make the transition, Maddie felt trapped by the military’s policy against permitting transgender people to serve openly.

“It was on my (kayak) trip when I decided I was tired of playing this game,” Maddie said. “Then came the other worries like getting kicked out of the military and my family possibly disowning me.”

But with a military regulation change in 2016, she decided it was time to finally be herself.


Until the regulation change, Maddie had only revealed she was a transgender to a select few people.

“I told my friend, who is a Marine in California, about a year ago,” she said. “Then I told his boyfriend. I’d never told anyone before. I was sick with worry. I felt like I was going to vomit.”

Next, she told her lawyer, a retired U.S. Army captain.

“He was bound by confidentiality,” Maddie explained. “And he’s my mentor.”

She came out to close friends as she worked up the courage to tell her family.

“I came out to my brother first,” she said. “He’s the most important person in my life.”

A devout Mormon, Maddie’s brother, Michael, told her those feelings were a sin, she said.

The reaction hurt her.

But Michael followed his initial thought with the explanation it would be a greater sin for him to not accept Maddie for who she was.

“I’m not sure what I would have done if he rejected me,” she said.

She came out to her sister before telling her mother.

“My mom really didn’t take it well,” Maddie said. “She really just resorted to making fun of me.”

During the conversation, Maddie said her mother told her she thought Maddie was dating an older man, who was manipulating her to go through the transition.

“I’ve never even flirted with a man,” she said.

Although Maddie said she thinks men are attractive, she’s only had relationships with women.


After her mother’s response, she was terrified her father’s reaction would be extreme as well.

“It was almost comical — I tried to come out to him several times,” Maddie recalled.

During one attempt, the two were sitting in a restaurant parking lot in Laramie, and the words were on the tip of Maddie’s tongue. Before she could speak, an older man wearing women’s clothing walked by.

“My dad cut me off when I was about to start talking and said, ‘Look, it’s one of those transgendered,’” she said laughing at the memory. “I was just like, ‘I’m not coming out on that note.’”

“But eventually, I just did it,” she added.

His reaction surprised her.

“It took a lot of courage for her to do this,” said John Holderegger, Maddie’s father. “I told her, ‘I don’t need to approve of what you’re doing — you will always be my child.’”

Before Maddie was born, John said he lived in San Francisco. Because homosexuality was common in the area, he said several of his friends were gay. Despite his conservative Wyoming upbringing, he learned to look past what the world deemed queer and see people as people.

“I think living around the totally different culture helped me be able to handle Maddie coming out,” John said. “Whether she’s my son or my daughter, she will always be my kid. If I’m in for a dime, I’m in for a dollar.”


While military regulations state a service member should visit a doctor to receive a diagnosis of gender dysphoria and inform their command before starting the transition process, Maddie didn’t quite abide by the book.

“I started my transition before I informed my command,” she said. “The regs said inform your command at your earliest convenience. So — I waited until the next drill weekend.”

When rumors of her transition rippled through the ranks before she informed her chain of command, she knew she couldn’t wait any longer.

“I called my team leader and said, ‘We need to talk,’” she recounted slowly to hang the weight of the situation on her words. “We went to Applebee’s, and I came out to him, and he was super cool about it.”

In fact, as the word traveled up the chain of command, Maddie said she never once received any kind of kick back.

“I try to remain neutral on as many things as I can,” said Capt. Ben Nemec, Maddie’s company commander. “My approach is, ‘OK, let’s see what the policy says.’”

For any other soldier, for any other situation, this reaction might have been a sigh of relief, but for Maddie, it was a boulder lifted from her shoulders.

As if a dam had cracked and given way, Maddie smiled and a wave of relief rolled over her expression as she remembered hearing about her commander’s reaction when her superiors informed him of her transition.

“The commander was awesome about it,” Maddie exclaimed. “He didn’t even flinch, and I think that’s awesome.”

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