We catch up with Pepa Mahogany, Key West Bear 2019… and now also 2020!

Pepa Mahogany has been up to a lot since we last caught up with him, which is right after the 2019 Key West Bear contest where he won the title of Mr. Key West Bear 2019. 

In his interview, we spoke about some of his goals for his title year, which included participating in the SMART Ride from Miami to Key West, donating children’s books and promoting diversity and inclusion in the Bear community. 

But, in the middle of his title year, Pepa was faced with an unforeseen obstacle that many titleholders were faced with — the COVID-19 pandemic. Because of the pandemic, many titleholders have had to postpone many of the goals they’ve set, and most of them will be holding their titles for an additional year. 

We had a chance to catch up with Pepa to see what he’s been up to since becoming Mr. Key West Bear 2019 and what his goals are for the upcoming year. 

Kyle Jackson: Hey Pepa! How are you, and what have you been up to since we last spoke? 

Pepa Mahogany: Hi Kyle! It’s a pleasure to be speaking with you again. There’s been so much since we last talked. I’ve learned a lot and have met/connected with so many people in the Bear community and beyond. Under my reign, I’ve been able to raise money for AIDS help and prevention with SMART Ride by participating in their bike ride from Miami to Key West and helping to contribute a total of $1.4 million! 

I also started a program to help bring the joy of reading to children called “Pepa’s Books for Tots”, where we donate children’s literature to kids. I’ve assisted with community events, such as the Key West Food & Wine Festival and volunteered at the Florida Keys SPCA Animal Shelter. 

I’ve participated in many protests for justice/equality, most recently in a joint effort with BetterHelp, which provides a free month of accessible therapy for those seeking support with mental health. It’s truly been an honor to represent Key West!

KJ: That’s great! I recently heard that Key West Bear Weekend is cancelled. Will you be holding your title longer now?

PM: Yes, I will now be holding the title as Mr. Key West Bear until November 2021, when we will have our next Key West Bear Weekend from November 4 – 7. So now, I’m a 2-year titleholder, which is pretty exciting! 

KJ: What are your goals for your extended title year?

PM: Well, just like everywhere else, the Keys took a big hit from this pandemic. We rely heavily on our tourism industry, so I want to help those that were greatly affected by it. 

My goals going into this new year are to continue focusing on helping my community by bringing awareness to causes that aid those in need of financial assistance, as well as creating my own platforms to showcase them. 

KJ: With the current crisis happening, has it changed your platform and goals a bit from when you first decided what they will be?

PM: Absolutely! A lot has happened this year so it’s put me in a different state of mind and direction with some of my goals. Although I’ve always been outspoken and passionate about social and racial injustices, when I first won the title, I kind of took a backseat on them in the first half of my reign. 

I felt this pressure to be a certain type of title holder — The one that only radiates positivity, takes selfies with motivational quotes and only shows all the good work they’re doing in the community. Although it’s very much a part of me, I kind of felt like I wasn’t living in my truth. There were so many things happening in the world, within our community and politically, that I wasn’t directly speaking about as authentically as I’m known to do.

.It was very conflicting because part of the main reason I signed up was to give visibility and a voice for those who were unseen or unheard in our community, and I feel I somehow lost sight of that in the beginning. I got caught up in the glamour of it all. I had to remember I didn’t sign up to be Mr. Congeniality, but to help make a difference beyond what I was already doing, and to be the type of leader that I want to see. 

I felt that I needed to trust my voice again, and when the pandemic hit, it reignited the flame in me. And when the murders of Ahmaud Arbery, George Floyd and Breonna Taylor happened, along with all the unnecessary murders of Black Trans women who just simply want to exist, I just couldn’t take it anymore. I had to speak up. 

My activism is very much a part of me and always will be, and  therefore I feel it’s part of my role as Mr. Key West Bear. 

KJ: That’s amazing to hear! So, with all the new restrictions, how do you plan to work social distancing into your platform if things don’t go back to “normal” soon? 

PM: I’m exploring the world of making virtual content from home, and I’m very excited about it! I’ve seen some incredible examples, including some shows that use the format, and it has inspired me to extend my own creativity to reinvent the way I reach out to folks during this pandemic. 

I want to create an entertaining variety show that will showcase artists as well as causes folks can donate to or get involved with. My goal would be to have it once a month or more, depending on how it all comes together and it would support the community. 

I already have my green screen and light stand, so I just have to play around with the technology and get comfortable with it. I’m really excited to see where it goes! I want to feature local talent and speakers, and even include others from outside the Keys. Of course, I’ll be hosting and providing some entertainment of my own as well! 

KJ: Can you talk a little bit about Honey Bear Tees and what you’ve been doing with them? 

PM: So, Honey Bear Tees makes these incredibly soft, comfortable t-shirts  and tanks that are geared towards the Bear community and admirers. They usually include fun pop culture references and internet memes. I was lucky enough to collaborate & give feedback with the artist/owner, Luis Paez, on a couple of his designs. 

The first was his “Black Bears Matter” tee he created, inspired by the Black Lives Matter movement. The BLM movement had a strong resurgence this past spring with all the police brutality and racial injustices happening to BIPOC. 

For me, the shirt goes deeper, because I do think it’s important our Bear brothers, sisters and folks to take an active stand in helping to create a community that truly is welcoming to all. When you purchase this tee, 100% of the proceeds go to LGBTQIA+ organizations that support Black Lives Matter. 

Now, the second tee was such a surprise, and I’ve been eagerly awaiting to share it with everyone. Luis drew a design of me to commemorate my reign as Mr. Key West Bear 2019… and now 2020… and it’s awesome looking! I’m so proud and ecstatic about it!

There’s a rainbow with a tropical Key West background, the Conch Republic flag, me with my sash and everything that makes up the essence of me. We even had a unicorn at one point, but he didn’t make the cut! (laughs)

This tee is available to buy on the website, and it comes in 8 different colors. Just search “Mr. Key West Bear: 2019/2020” and make sure to check out all the other designs. He’s got some great stuff!

Follow Pepa Mahogany, Mr. Key West Bear 2019, on Facebook and Instagram.
Follow Honey Bear Tees on Facebook and Instagram, and visit to order!

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Kyle Jackson

Kyle Jackson (He/Him) is Senior Staff Writer at Gray Jones Media, and additionally works as a writer, editor and theatre artist/actor. A native of New Orleans, Louisiana, he studied at Dillard University, received a BA in Theatre from Morgan State University, an MS in Arts Administration from Drexel University, and completed the British American Drama Academy’s Midsummer in Oxford Programme in 2017. Having lived in Baltimore, the Washington, DC area, Philadelphia and New York City, he now resides and works in London, United Kingdom.