Breaking Barriers

The first transgender Mr. Connecticut Bear wants to bring people together

By Jane Latus

Masculine and rugged. Big and tall. Muscular or stocky. Above all, hirsute!

The clichéd descriptions of a bear are physical and allow for only a little variability, mostly of weight.

But Kylar Maldonado, Mr. Connecticut Bear 2020, is no cliché.

The Portland resident, now 22, became at 21 the first transgender man to be named Mr. Connecticut Bear. He entered the competition at the urging of his boyfriend Eddie Brewer, a full-time nursing student. After winning, he got a congratulatory hug from his mother, Kimberly Burr, also of Portland. The competition is organized by the Northeast Ursamen, a non-political, gay fraternal organization that promotes bringing people together in a variety of safe and fun social events.

Maldonado is a shift leader at a D’Angelo sandwich shop. When he and Brewer aren’t working, they do partner acrobatics and travel for fun.

I asked him to tell us more about what it means, especially as a trans man, to be Mr. Connecticut Bear.

Q: You are a barrier breaker. Where do you stand as a record-holder for trans bears?
A: I’m the first trans man to win Mr. Connecticut Bear. Worldwide, I’m the second openly trans man and the youngest, at age 21, to win the title internationally! There are actually other people who have won similar titles, but I’m not sure if they’re out. Some of them prefer to be stealth. But, do know, others do exist!

Q: When did you transition and was your family supportive?
A: I was 17. I wrote a letter to my family coming out as a trans guy. It wasn’t easy. My mom didn’t want me to start hormones until I was 18. She knew I had friends who were trans, but when it’s your kid and you don’t know what to do, you panic. What made her come around was when I told her that I didn’t want her to be like the people she was afraid of me for. That scared her, when I put it to her like that. My mom’s amazing!

I worked with GLSEN [a nonprofit that works to end discrimination and harassment based on sexual orientation and gender identity] since I was 15, so my mom knew I’ve got this. She knew this was something I’m very knowledgeable about.

Q: How did you discover the bear community, and how did you get involved?
A: It was a mix of online, like hook-up apps, and through friends at Pride events. The community is still very small in Connecticut, but I started hanging out with others, getting to know them. Thankfully, I was soon connected to people who were part of the Northeast Ursamen, which is not only the organization that runs the CT Bear contest, but is a nonprofit that hosts community events such as Spookybear, Out of Hibernation, and Bears Dine Out.

Q: What made you decide to compete?
A: Uh, (laughing) my boyfriend.

Q: I’ll rephrase that. Who made you decide to compete?
A: My boyfriend! I’d been wanting to do it for a few years, since I saw another title holder wearing his vest at Pride in the Park. I was like, “Why do I want to do that? Why does it look like something I want to do?” At that time, I wasn’t exactly a bear, so I wasn’t sure why I was thinking this. I was in that weird area of my life where I started questioning my sexuality and gender after being out as a lesbian for two to three years. But as time went on, I knew I really wanted to compete and make a difference on a bigger platform. Last year was the first year I finally was old enough. I wasn’t sure I was ready, but my boyfriend was like, “No – you’ve been wanting to do this, and you need to do it this year. It’s something that means a lot to you.”

Q: What defines a bear?
A: When I was a lot younger, it was definitely more based on physical characteristics. But everything with gender is continually progressing and changing. So being a bear, or a cub, or an otter, or whoever in the community, has become more of a state of mind than what you look like. Some who look like they would belong in the bear category don’t even identify as part of it. I know others who weigh 15 to 20 more pounds than I do, but they still have the title of cub. So it just depends on what you feel you identify with.

Q: So a bear doesn’t have to look like a lumberjack?
A: Stereotypically, it’s more common than not to look like that, yeah. But there are all kinds – there are femme ones, and more masculine ones. I have tons of friends who identify as bears and happen to wear makeup better than I would have ever in my life, and even do drag! (Laughs.)

Q: What does the competition entail?
A: It entails a meet-and-greet, a dance party, and an interview conducted by five judges – all previous or current title holders – and people of the community. There was an onstage portion where I modeled lots of looks, like a pageant – and then a pop question. I had a formal look, a hot look and a bear look. The question was, if I had a sitcom, what would it be? I said it would be based on my family – my mom always tells me, “You could write a book about it and nobody would believe it, because of how crazy we are.”

Q: What is the responsibility of Mr. Connecticut Bear?
A: The role of Mr. Bear is to connect with the community by outreach. They want somebody who will be a good representative. You’re obligated to attend certain events held by the Northeast Ursamen, but you also fundraise for charities. I try to be visible in all LGBTQ communities like drag, leather/kink, and more, especially by volunteering at their events.

Also, my mom and I travel a couple times of year and speak about my transition, and how transitioning affects the family, too. We’ve spoken at trans conferences like True Colors, colleges, and wherever we get booked.

Q: How do you explain to others what the bear community is about?
A: It’s a state of brotherhood and family, alongside with having a good time. The bear community in Connecticut has become rather – I don’t want to offend anybody – but generally an older crowd. That is something that I was worried about when coming out to this community. I didn’t want to feel left out or underappreciated due to my age. Also, the trans bear community is even smaller so I was worried I wouldn’t be able to connect more personally along those lines. I want to create a bridge between the older crowd and the newer bears – cisgender or trans, vanilla or sexually explorative, white or people of color, and more. It’s about enjoying each other’s company, and being there for other people’s communities, not just for our own.

Q: Tell us about your platform.
A: My platform is acceptance and inclusivity, for all identities. As someone who is Latino, trans, queer and very young – all that – I want to make sure that no one is left out. I never attended bear events when I was younger, because they were all 21-plus, or they were always at a bar, so it was always a barrier I’d run into. I was interested in the bear community ever since I was 17.

I just want to have more of an intersectionality between other communities, like the drag queen and leather communities.

The bear scene in Connecticut is mostly a white, older crowd. That’s why I hold my events in more racially diverse places, like New Haven or Hartford. If we want to have more people to attend our events – of different races and ages, different everything – we need to go to them.

I’m organizing an S&M Dinner – spaghetti and meatballs – with Mr. Connecticut Leather 2020 Mark Richards – who also happens to be my sash grandpa (laughs) and Imperial Sovereign Court of All Connecticut 2013 Empress Morgana De Luxe. I’m hoping to draw more people than what has been commonly seen in our community previously.

Q: Tell me about your chosen charity, Boston-based The Network/La Red.
A: About two years ago, I was finally able to get out of an abusive relationship with my ex-boyfriend. When I was looking for a charity to donate to, this one got my interest because they are a survivor-led, nonprofit organization for LGBTQ people trying to get out of abusive relationships, including BDSM, polyamorous, and more. It is an organization that I wish I could have known about when I truly needed it.

Q: How does being trans intersect with being a bear?
A: As a trans person, you constantly face people within the bear community who don’t understand it. A lot of people think you can’t be a bear because you were “born a girl,” and you can’t be a bear because “bears have penises.” Some people are very … harsh. But there are also people who’ve done nothing but build me up and protect me. They have always given me appreciated affirmation.

Q: Was being trans an issue in your competition?
A: I don’t think so. And if there were, it wasn’t on my mind. I was focusing a lot on myself and to be honest, my other competitor. As they were a friend of mine, we did check-in meals to make sure our mental health was okay and that we were ready to face anything that could have been brought to our attention. But the people around me really kept me busy and on track for the title. The people who helped me compete – who did mock interviews and stuff – they’d either won the title before, or they’ve been nothing but supportive of me. The judges were all super nice and they all knew of me due to my activism presence.

Q: What is the rest of the LGBTQ community’s perception of bears?
A: People commonly see the bear community as an older crowd of people who just like to hang out among themselves. Which brings me back to why I want to intersect with all communities. Especially in Connecticut, we all get along. Connecticut is awesome because the lesbians hang out with the gays, the drag queens hang out with the bears and leather people. Everybody hangs out together. I guess I am always shocked when people say that it is quite the opposite for them in other states.

Q: Is there a move toward body positivity in the bear community?
A: There are always people who will think I’m too skinny or too fat, but that’s like the world in general. But the current Mr. North American Bear is two or three times my size, and everybody adores him just the same. The community has been quite accepting of all body types, for the most part. It’s something I’m really surprised about, because when I was younger, I thought being heavier was an issue. But nobody cares about physical appearance as much as I thought they did. We care more about well-being, making sure everyone is happy and healthy, and what they want to be in their life.

Q: Just like some people incorrectly think that four-legged bears really sleep all winter, are there any myths about bears you’d like to dispel?
A: It’s commonly thought that we’re dirty, rough, aggressive and mean people. But I’ve been called a teddy bear a lot. People always tell me, “You look so intimidating, but you’re really so nice!” People think we’re very masculine, keep-to-themselves people. But we’re not. The people I keep around me are very genuine and honest people, but very kind and sweethearts.