
It was Friday, August 25, 2017, and Kallie Winners was getting ready for work just like any other day.
Getting ready to head out the door, a fellow Tesla colleague send her a text message. “I support you and I’m honoured to know you,” it read.
In a response, Winners turned on the news.
“I just knew something had happened,” Winners recalled.
On TV, every news station was headlining the same story: President Trump had signed a directive banning all transgender individuals from serving in the military, rescinding President Obama’s policy.
For current trans service members, it means that they may soon be asked to leave. For trans people wishing to serve, it means they won’t be accepted.
“I remember feeling so dejected. I served for nearly a third of my life, a decade on active duty, and for the first time I felt like my country didn’t have my back,” said Winners.
Winners spent 10 years on active duty as a machinist in the US Navy, six years and 10 months of that time was spent on sea duty, deployed in the western Pacific four times. Since leaving the military in 2009, Winners earned an engineering degree, gained some years of professional experience and completed her gender transition in 2015.
All the while, she missed the military terribly. So when the Obama administration lifted the transgender ban in June 2016, allowing transgender Americans to serve openly, Winners started taking steps to return to the military in the US Navy Reserves program.
“The camaraderie, the mission, being part of something bigger than myself was something that I desperately need in my life,” explained Winners.
“I had a few years left before I was capped by age, and only needed to start my masters program. I had been working towards that goal when the current president took office.”
Winners, now 37, has only two years left before the enlistment age cap applies. But since Donald Trump’s current term as US President will continue for another three years, a return to military is highly unlikely for Winners, and it’s a reality she struggles to come to terms with.
“Have I come to peace with it? No, no I don’t think I have,” Winners said scoffing. “I am still very angry about the President’s decision on transgender service members. I get really stirred up about the level of injustice coming from a country that I spent a decade of my life serving. I hurt and I am frustrated for myself, but more than anything, I hurt for transgender service members that are on active duty because they are wearing the uniform right now and they are counting down the days essentially until they are asked to leave. My heart breaks for them.”

Photo by Rhys Harper
Becoming herself
Winners credits the military for saving her life. She was a troubled teenager, a homeless high school dropout and drug addict who was heading down a road that only has one outcome.
“One morning I woke up and realised that I needed to do something different or else I wasn’t going to make it. A good friend had joined the Navy and suggested I should join also. Six months later I was on my way to boot camp,” Winners shared.
“The military changed my life. It gave me a level of pride, motivation and deep love for my country that I carry with me every day.”
But even in the military, things weren’t quite right.
“I had always known that there was something different about me, that my body just didn’t feel right. It wasn’t until well in to my military career that I learned about the term transgender and what it meant. I knew that it described how I had felt for so many years,” she said.
“I also knew that I had to separate from the military to try to figure this out.”
Winners left the military in 2009, sought help and started hormone therapy the following year.
She was undergoing this process while attending University, and it wasn’t until halfway through her senior year that she started her outward transition, presenting as female for the first time.
“I remember the first time I went out, presenting the right gender during the day. It was nerve wracking and terrifying but it was also the first time that I had felt 100 percent in my body in public. It was an amazing experience,” she said.
Finding camaraderie in cycling
Fast forward a few years and Winners is living as the truest version of herself, but a part is still missing.
“I miss the camaraderie of my shipmates. Civilian life just didn’t have that,” she said.
Until she found cycling, that is.
Riding bikes isn’t new for Winners. She had briefly raced BMX as a kid and when things got rough at home, a rickety old road bike offered an escape.
Bikes re-emerged into her life after the military, and with it, she found the closest thing to that military camaraderie that she longs for.
“I had watched racing for a long time, and always admired that beautiful symbiotic relationship everyone has in the pack during road racing. I always wanted to be part of that but being one of the guys never fit right,” Winners said.
That moment that she finally lined up for her first race — a crit in Colorado — surrounded by her fellow women, is a day she’ll never forget.
“When they said ‘go’, we all hit the gas and around the first turn I was bar-to-bar with the women next to me and I was like ‘holy shit, I am racing. On a bike. With other women!’,” Winners recalled. “Looking around, I was so elated. Just to be part of that with other women, was a big goal of mine and just a really cool experience.”
Where the military gave Winners a sense of pride and purpose, the bike gives her a sense of achievement.
“Whether I come in first or last, I feel like I have accomplished something. Cycling is a physical and mental challenge, and it gives me this sense of achievement that I don’t get anywhere else.”
“The bike is many things,” she continued. “It can be my reward. It can be my punishment. It can be my escape from reality. It can be a way to bring me back to reality. It really depends on what is going on in my life. Right now, cycling for me is a way to stay in touch with my body. To focus on something outside of work. And to connect with the environment around me.”
The bike also keeps her connected to the military.
Winners is an active member of the US Military Endurance Sports program (USMES), a non-profit 501(c)3 organization chartered to support endurance sports education and activities for current, retired, and veteran members of the United States Armed Forces.
“USMES and Team Rubicon, both awesome organizations run by veterans for veterans, have helped me and continue to help me be the best civilian I can possibly be,” said Winners. “They have provided me with a support structure that I haven’t had since I was in the military. Unwavering level of support that only military veterans will understand.”
Being trans in the cycling world
But being trans and an athlete opens up a whole new can of worms. When fair play and the sanctity of sport is at stake, emotions run very high, very quickly.
“My favourite argument against trans athletes is always that some guy, somewhere, is going to pretend to be trans to get ahead, to win a race against women,” said Winners.
“It is just a ridiculous argument. No guy is going to pump their body full of oestrogen to win a race against women.
“Transitioning was one of the hardest things that I have ever done. Going through a second puberty at 31 years old is a nightmare,” she continued. “And on top of that there is all the social anxiety and hatred in the world you get to deal with. It is awful! Nobody would choose to do that just to win a bike race.”
Fortunately, Winners said that it’s never been an issue at USMES, nor her local racing scene.
“USMES is and always will be a welcoming community for all those who have served their country,” commented USMES Executive Director, Bill Jacobus. “We want to be clear that we support everyone in the military and veteran community working to lead active lives.”
As far as the racing scene goes, Winners said she’s received nothing but support.
“One of the things I have always loved about the cycling community, specifically other women, is that we are all very accepting and supportive of one another,” she said. “In Cat 4-5 races, nobody cares. We just want to get our feet wet, have fun and be part of a community. When you start to get into the Cat 3,2,1 and pro I can see that people take it more seriously and it gets more complicated.”
By complicated, Winners is, of course, referring to new policies that require trans athletes to provide medical records demonstrating testosterone levels in order to compete in elite level cycling events.
Adopted in July 2017, USA Cycling has a two-pronged transgender policy: self-declaration for category 5, 4, and 3 athletes; the revised International Olympic Committee guidelines for athletes competing in category 2 and up.
Briefly stated, the IOC policy allows transmen – riders who were born female – to compete in the men’s categories without restriction, while transwomen – riders born male – are ineligible to compete in the women’s categories without first undergoing a sex-confirmation surgery upon meeting some strict rules set around testosterone levels.
Part of the criteria is that the athlete must provide medical documentation for 12 months prior to her first competition, and can be subjected to random and for-cause testing.
“I have mixed feelings about the new rules from USAC,” stated Winners. “It provides trans people a way to compete, but doesn’t treat trans people equally from non-trans people. In my opinion, if trans people have to provide some level of testing to compete, than every athlete at that level should have to provide the same testing, only then will trans people be truly treated fairly in sports. So while we’ve made steps in the right direction, there is still much work to do.”
For now, however, Winners is a category 4 racer and free from said scrutiny, and the bike can just be a tool to find her footing and peace with civilian life.
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