In a lot of ways Jay Robinson was your average competitive collegiate rider. He excelled in his dramatic writing program and in the saddle, competing in intermediate flat and open fences and regularly winning ribbons. But the barn had a special meaning for him: It was a safe environment where he could fully express himself as a transgender man.

Robinson’s friends describe him as loyal, a keen observer, a people pleaser and a hard worker who never complains. He entered college as an extremely shy person, but as he went through his gender transition and came to accept himself, he found his footing and came out of his shell.

“It’s wild how much he’s changed over five years,” said Maddy Skrak, who served as his “big sister” on the Mount Holyoke (Massachusetts) riding team. “He’s a new person now, and it’s incredible. You could tell he was a bit uncomfortable in his own skin when he first came to Mount Holyoke. He slowly gained confidence in all these little moments leading up to him finding out who he was.”

A Major Realization

Robinson grew up as a typical pony-crazy kid. He caught the horse bug early, and his sister Sophie Robinson, three years his junior, followed in his footsteps. They spent every spare moment at the barn, first in an academy program, then eventually with their own mounts.

When it came time for college, a blog post caught their mother’s eye. In it, the writer extolled the virtues of an all-women’s college as it had helped her find herself and build confidence. Soft-spoken as a teenager, Jay, who was assigned female at birth, agreed that sounded like a good idea and started looking at Mount Holyoke, drawn by the school’s stellar academics and strong riding program.

Jay Robinson found supportive environments in the stables at Mount Holyoke College (Mass.) and the Savannah College of Art and Design (Ga.) as he embarked on his gender transition. Photo Courtesy Of Jay Robinson

His senior year in high school he took an overnight trip to Mount Holyoke—staying in the dorms and visiting the stable the next morning—that sealed the deal.

“Everyone on the team was so knowledgeable and welcoming,” said Jay, 23. “The thing that sticks in my mind the most is that [head coach] C.J. [Law] was having her students do an exercise where they had to balance a pebble on the top of their hand while they were riding, and they couldn’t let the pebble fall. I was blown away that all these riders could do this. I was like, ‘I want to be able to balance a pebble on my hand! I’m going to have such still hands; it’s going to be great!’ I knew that I would learn so much.”

Jay headed off to South Hadley, Massachusetts, excited for the college experience. He studied psychology, thinking he might follow in the footsteps of his parents, who were doctors, and he focused on improving his riding with Law and the team. He headed to his first tournament in September, just weeks after arriving at school, immediately bonding with his teammates during their long drive to Virginia. He competed regionally with his school and loved the camaraderie he felt with the other riders.

When Jay went home for winter break, he naturally headed to the barn to get a horse fix and see his old friends. One of them, a trans man named Eric Beam, had just undergone top surgery.

“Everyone was so excited for him,” Jay recalled. “I remember him lifting his shirt so that everyone could see, and I felt so jealous of the fact that he had a flat chest. I’d never been comfortable in my body. Once puberty hit I really started feeling uncomfortable in my body just because it did not look the way I wish it did. I was so jealous of how good he looked. I just wanted to have his body, essentially.”

Jay went home feeling confused and flustered, unsure why he was jealous of his friend. Eventually Jay reached out to Beam to see if he would understand why he felt so uncomfortable in his own skin.

“He was like, ‘Obviously I can’t tell you that you’re trans. But if you’re having these feelings it’s worth acting on them and see how it makes you feel,’ ” said Jay.

So when he returned to school Jay sent an email to his teammates asking to be called Jay and to be referred to with gender neutral or male pronouns. He didn’t know what to expect, but what he got was an outpouring of support. A handful of teammates emailed him back to affirm his decision, and the next day Jay went to the barn for a lesson and saw that his name had already been changed on the board.

“After the first day of doing that I was like, ‘This feels right,’ ” Jay recalled. “ ‘I like when anyone calls me Jay and uses male pronouns. It doesn’t make me cringe when people say my name and reference me using [female] pronouns anymore.’ I reached back out to [Beam] and said, ‘Hey, took your advice. I have to say I like being referred to as a man.’ He was like, ‘OK, I think you have your answer.’ And I was like, ‘Yeah, I think I do too.’ ”

Coming Out

Jay came out to Sophie while they were playing basketball on a family vacation. He’d already chopped his long hair short and was wearing more masculine clothes, and he told her that he’d been going by “Jay” at school.

“I remember telling him, ‘Jay, whatever makes you happy,’ ” she recalled. “He had been struggling for years on self-love and really loving himself for who he is. It didn’t matter how many times someone would tell him how great he was. I just wanted him to feel good about himself. When he officially came out, it was definitely a transition from having an older sister to older brother in that I had to knock on the bathroom door—we share a Jack-and-Jill bathroom between our rooms. But it’s not like he changed who he was; he’s the exact same person he was before he transitioned. In fact he is happier and does feel more comfortable than he ever was before.”

While at college, Jay Robinson and his service dog Sage spent every spare moment at the barn. Photo Courtesy Of Jay Robinson

Jay had come out to his parents once before while a sophomore in high school.

“They took me coming out as a lesbian great,” said Jay. “ ‘Well, whoever you want to love, as long as you’re happy, we really don’t care what you do.’ ”

But his parents had a harder time when he called them from Mount Holyoke to tell them about his gender identity.

“I think it’s because it was harder to understand,” he said. “I guess it’s one thing to be like ‘Yeah, I’m attracted to women not men’ instead of, ‘Yeah, I am a man not a woman.’ My mom ended up leaving the conversation when we were on the call. My dad and I just kind of wrapped things up saying we were going to revisit it at a later time. When I spoke to him again, he was like, ‘Yeah, your mom needs some time. We want to make sure this isn’t just a phase.’ ”

Jay and his mother went some time without speaking while she processed the change and mourned the loss of her daughter. Jay considered not going home for the summer, but in the end he headed back to his parents’ house in Larchmont, New York. There he threw himself into working at the barn, showing up at 7 a.m. and sometimes not getting home until 10 at night. He also started gender therapy, and after a few group sessions with the therapist his parents began to truly accept their son. Meanwhile Jay was contemplating the next steps in his transition, namely hormone therapy and top surgery. While his parents didn’t balk at these steps, they left it to their son to make all the arrangements.

“People don’t realize that it is a mourning process for people,” said Jay. “I would even say that I went through a little bit of a mourning period. There is this conception that when people go through this transition, they become an entirely different person. I don’t want to lose who I am. I don’t dislike who I am. I just don’t like my body and want my body to match how I feel inside. I was scared that I was going to change somehow because I was going through all of these changes. I think having the horses there to keep me consistent when I was going through so many changes helped keep me grounded.”

Back at school Jay found a supportive environment, both within the greater Mount Holyoke community and, especially, on the riding team.

“I remember having Jay in my office and worried about what was going on at home,” said Law. “I had met his parents. I knew that they were loving parents. I think it was hard for them to accept. I kept telling Jay, ‘They’ll come around, don’t worry. Somehow you’ve got to believe in your parents. You’ve got to give them time.’ ”

The rest of the team, including Skrak, was there to support him too.

“Jay and I had become so close. We’d gone through interesting moments, the hard parts of transitioning,” she said. “It’s not all pretty; it’s not all fun. It’s really hard and scary. You have what feels like an unaccepting world going against you in a lot of ways even though you’re on a very accepting campus. It was really hard. There were a lot of tears and tough moments.”

Making Changes

After coming out Jay had a tough decision to make. Should he stay at the women’s college where he’d developed so many wonderful friendships and a strong bond with his teammates and coaches or move on to a coed school? While Mount Holyoke is an all-women’s institution, the school is gender diverse and accepts trans and non-binary students. But Jay realized that as a man, having Mount Holyoke on his résumé would raise questions in future job interviews.

“Just getting dressed for a show, when I tightened the tie around my neck, I felt safe and confident,” said Jay Robinson. “I felt like I was finally showing everyone else who I had been on the inside all along.” Alison Hartwell Photography Photo

“I’m not hush-hush about my trans identity, but you can’t tell I’m trans just by looking at me,” said Jay. “It’s not something I tend to bring up willy-nilly. It’s not a conversation I really want to have with a potential employer, describing my whole life story, so I was like, ‘I think in terms of the future it might be best if I transfer out to a school that’s coed.’ That was the breaking point for me there.”

That summer Jay began leaning into his trans identity. He started buying men’s show clothes, which made a big difference in how he felt, and his dad taught him how to tie a tie.

“You wouldn’t think it would make that big of a difference in men’s versus women’s show clothes because I know the differences are not tremendously drastic, but it was,” he said. “I compare it to the first time I sat on my horse. I knew the second I sat on him I felt safe; I felt comfortable; I felt at home, and I felt at peace. Just getting dressed for a show, when I tightened the tie around my neck, I felt safe and confident. I felt like I was finally showing everyone else who I had been on the inside all along.”

Jay decided to take a year off from college while he worked with the gender therapist in Manhattan. Trans people who would like to receive hormone replacement therapy or undergo top surgery must receive a letter from a medical professional like a gender therapist stating that they are medically necessary procedures.

In the meantime Jay rode once a week and took classes at New York University, half an hour from his home in Larchmont, as a visiting student. He enrolled in a creative writing class on a whim, which inspired him to set aside his psychology ambitions and focus on writing. When it came time to apply for schools, he added the Savannah College of Art and Design (Georgia) to the list thanks to their dramatic writing program—and their nationally recognized riding program.

“It was summer, and I was seriously starting to talk about hormone therapy with my parents and getting my letter so I could start that,” he said. “I didn’t think I’d be able to cope with all of those changes and everything by myself. I knew that the horses had kind of been my happy place. I figured no matter how bad things got, as long as I had the barn to go to at the end of the day everything would be OK. So that’s why I ended up choosing SCAD because I didn’t think I could do it without the horses. And looking back I really don’t think I could have.”

A Cathartic Moment

Jay feared he’d never find an equestrian program as educational and supportive as Mount Holyoke’s, but he was thrilled to be proven wrong at SCAD.

“I feel like C.J. really gave me the knowledge that I wanted to get where I wanted to be, and [SCAD head coach] Ashley [Henry] gave me the techniques that I needed to get there,” said Jay.

Jay was supposed to compete at the first show of the season, but he fell off and dislocated his collarbone. Once he healed from that injury he went in for top surgery, which would take him out the rest of the quarter.

His first show back was a two-day affair, and Jay, generally an over fences rider, would be competing on the flat both days. He’d always been self-conscious about his riding on the flat and had a habit of hunching his back and rolling his shoulders forward, which he attributed partly to riding with a binder to compress his breasts before his top surgery. While he feared he’d disappoint his team, he had faith in Henry and her decision to have him compete on the flat. The first day didn’t go well.

“I remember the look on his face when he came out of the ring like an, ‘Ah, I knew I wasn’t going to do well’ sort of face,” recalled Henry.

Later she sat him down alone to give him a pep talk.

“I was like, ‘You are going to go in there next time and going to say, “I’m going to do good. I’m going to be strong, and I can take a deep breath and face this judge and competition just like you can face the world.” Look at all the amazing things that you’ve done already!’ I could definitely see the fight in him a little bit,” she said. “You have to have that fire. Sometimes students are a little bit shy to carry that torch. You just have to put it in their hands and help them stand up a little bit taller.”

Jay took her words to heart.

“So I felt like, ‘Look, I’ve gotten this far, there’s nothing to be ashamed of. I can roll my shoulders back, show everyone my chest and be confident in who I am, and I think that it’s worth a try. Let’s see if that makes a difference,’ ” he said. “And it did because I ended up winning the class the next day. That was my first flat class I’d ever won for the IHSA. It was definitely the first class that I had won since transitioning.”

A pep talk from SCAD coach Ashley Henry brought out Jay Robinson’s confidence, resulting in his first win on the flat in the IHSA. Photo Courtesy Of Jay Robinson

Disciplined, Organized And Humble

Jay brought a no-excuses attitude to his teams, and he led by example, keeping up good grades and volunteering at the barn outside of lessons. He also has Type 1 diabetes, and while he was at SCAD he acquired a medical alert service dog named Sage who can smell when his blood sugar is fluctuating. But before he got Sage, few people knew about his condition.

“Jay was never like, ‘Oh, I don’t think I can do the two-mile run this morning because my insulin levels are low,’ ” said Henry. “One time in the history of the team he looked at me and said, ‘I think I need to get some Skittles. My blood sugar is a little low.’ A lot of students advertise about their life, but he kept things professional. He was always disciplined, organized and very humble.”

He also became a friend many knew they could lean on.

“Jay is the sweetest, most caring person I’ve ever met in my life,” said SCAD teammate Halle Wilson. “He’s the type of person who’d be there for you in the middle of the night if you needed something. He’s all of our No. 1 cheerleaders. He’s also really talented with the nervous horses. He could get on the craziest horse and make it look like it was the easiest thing to do.”

According to Skrak he had a huge effect on the people around him, including opening her own eyes to the trans experience.

“There’s a saying at Mount Holyoke: ‘We’re a community of pioneering women,’ ” said Skrak. “It’s kind of like Jay was our own pioneer for our riding team. Although we had a trans policy and a strong LGBTQIA+ community, he was the first person to plow through different pronouns on our riding team. The riding team wasn’t the most diverse club on campus. Although we represented many LGBTQIA+ elements, the trans part of that wasn’t included until Jay. I think people will feel so much more confident and comfortable being themselves because Jay paved this path for them.”

Jay didn’t ride on the team during the fall of his last year at SCAD as he was furiously at work on his portfolio for school, and he didn’t want to do a subpar job at classes or in the show ring, but he still squeezed in some saddle time. He’d planned on coming back to the team his final semester last spring, until COVID-19 canceled the season. After graduating in May, he moved to the Los Angeles area to be closer to Sophie and focus on screenwriting—but he plans to keep riding.

“Riding is a lifestyle,” said Jay. “It’s not a hobby, and it’s not just a sport. I at least know now that I have to have horses in my life in some capacity because I don’t feel whole without them.”

This article appeared in the October 19 & 26 issue of the Chronicle of the Horse. 

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