“The Cowbear"

After the last portrait blog post, I wrote about a ride you would go on… Well, now it’s time to take you on the journey I had to endure for this portrait. Before we continue, I want to mention that I am not looking for any drama after posting this. It’s not worth my time or the model’s time. We have already resolved everything and have talked both through messaging apps and in person about what happened on November 23, 2024. So again, please don’t send any hate to anyone in this story.

How We Met

After I finished my self-portrait, Acceptance, I received a message from Cowboy Duke on Instagram. I followed him back, and we started chatting about my artwork and some of the model shots he had taken. We also talked about his job. At the time, I had no idea who he was, so I responded, and then the conversation ended. I didn’t think much of it and went on my way to the Inaugural Keystone Leather Contest. Not knowing anyone there—and since this was my first leather contest—I was nervous. I had never been to a contest before, so I didn’t know what to expect. I only paid for Saturday and, once I arrived, I hopped on Scruff, the gay dating/chatting app. That’s when I got a message from him: "There’s no way you’re here right now..."

At the time, I had a vague familiarity with him. I told him I had just arrived and was relaxing at the pool with my friend Gus, who has been by my side throughout this entire journey. I looked up at the top of the stairs and saw a six-foot-five-inch cowboy walking down toward me. I was overwhelmed—and very attracted to him. He was one of the judges for the leather contest that was happening. I hadn’t really paid attention to who the judges were, but it felt oddly coincidental that our paths had crossed just two weeks after he first messaged me on Instagram. When I met him in person, he seemed strangely familiar in both a good and bad way. At the contest, I was surrounded by people—some I knew, some I didn’t. To them, I was fresh meat. I was in my first year of being a leather man, and while I wasn’t intimidated by the people, I was curious about what these contests meant to them. Now, before anyone messages me—I didn’t take contests as seriously back then. I just knew that many people around me, and around the world, held titles, but I didn’t fully understand their significance.

I had an amazing time at Keystone on Saturday and messaged my friend Gus that night, saying, “Hey… want to go back tomorrow?” He said absolutely, so we went back on Sunday. I returned for the contest—but also to get a better read on this Duke guy I had just met. When I “investigate” someone, it’s not like a detective; it’s more psychological. I wanted to pick up on his past because I had a strange feeling we had talked before. Sunday came, and I wore my black wool kilt with a leather vest—which turned out to be a terrible idea in ninety-degree weather. I ended up taking the vest off for about an hour while sitting outside by the pool. Throughout the day, he was constantly on my mind and within my sights. I wasn’t stalking him by any means, but I couldn’t shake this funny feeling about him. The contest went on, and all the contestants won by reaching eighty percent of the required score. Duke—who, at the time, I didn’t realize was the 2022 International Mr. Leather first runner-up—gave a speech about bootblacks and their importance to the community. Back then, I just assumed bootblacks were the cornerstone of the leather community and were treated well. Little did I know, huh?

About 30 of us, dressed in full leather, went to an Italian family restaurant. As we pushed tables together, the other diners—mostly straight families—watched us with curiosity. Of course, I sat next to Duke. I wanted to get to know him better. We talked about his family, my family, and everything in between. To me, it felt like we were both interested in each other. That evening, while everyone was chatting and smoking cigars, I took a break from the conversation and looked out at the field. The cicadas hummed in the distance as voices murmured behind me. It was around ten at night, though I had planned to leave by nine. But I didn’t want to go. Strangely, I felt at home. Then Duke came up behind me, and we shared an intimate moment. That’s when I felt the connection—like it had always been there. He walked me to my car, and I told him how I felt about him. He kissed me and said, “Call me every day…” I got into my car and drove home, and guys—this was one of the hardest drives of my life. It felt like my heart was breaking, like I would never see or hear from him again. A few days after the contest, I couldn’t get Duke out of my head. It felt like I had this intense crush on him. But when I tried calling… it went straight to voicemail.

The Longest Day Of My Life

After that, I worked on The Spiritual Sir and The Recruit. As I searched for the next models for my series, my first thought was Cowboy Duke—not because I liked him, but because he had the cowboy look I was going for. Plus, from my perspective, he seemed to be involved in the leather community. When I reached out, he responded immediately with a “Yes.” I was stunned. I had thought this man had fallen off the face of the earth, and suddenly, he wanted a free portrait of himself… Anyway, I scheduled our photoshoot for 3 PM on November 23, 2024, right after Ken’s portrait. But we all know what happened—Ken was doing community service, so I ended up heading to Duke’s apartment early. When I arrived, I had no idea where I was. I had driven past the Pentagon and thought, “Oh, that’s where I am?” Now, to be clear—Pat (me) had never been this far south alone in my life.

I arrived at Duke’s place around late afternoon—around twelve-thirty—and waited for him. Then, I got a message from him saying, “I thought you were going to be here by three.” I quickly explained what had happened, but he just told me to go home. After driving six hours down to Washington, D.C., just to see this man—who, at the time, I had a crush on—he simply told me to turn around and leave. After burning through more than half a tank of gas, that was it. Frustrated, I got back in my car and tried to convince him that I could just come back later. I promised I wouldn’t take up too much of his time and that I’d head home soon after. But no matter how convincing I tried to be, the answer was still the same—I was told to go home. I do want to take a moment here to apologize to Duke for the long messages I sent him. I basically poured my heart out, telling him that this series was all I had in the world. At the time, that was true. And honestly? It still is.

In the middle of my drive back to Pennsylvania, I stopped for gas and thought… I should just go to The Bike Stop and be with people I know. That day, I felt more shell-shocked and betrayed by the community than ever. I did end up going to The Bike Stop for BLUF Philly. I sat at the bar, exhausted and emotionless. But while I was there, I made a new connection—Michael Jeavons. He runs the NYC BLUF social and has strong ties in the art world, including connections with Durk Dehner, a model for Tom of Finland, the artist who inspires me. Dehner also co-founded the Tom of Finland Foundation, which helps smaller artists gain exposure—something I really need. I love what I do, but exposure is crucial for any artist. Michael and I talked more about art, and he seemed like a genuinely nice person. He left early, and I stayed with my friends. Later, I was invited to an after-party, but I was completely drained. I barely had the energy for anything at that point. I just hoped I’d get a chance to relax and catch my breath before heading home. I finally made it home at two in the morning. After being awake from 7 AM to 2 AM—nineteen hours straight—most of which I spent driving to D.C. and back, I was completely spent.

The Climax

On Sunday afternoon, I felt overwhelmed with emotion over everything I had just endured. I had traveled all that way for nothing and felt even more heartbroken over a man I once thought was the kindest person in the world—only to be hurt by the very same man I had met at Keystone. At the time, I was working on a drawing of Master Steeltoe. I sat on my bed, crying for about half an hour, completely drained. Then, I looked up at his portrait and felt an undeniable pull to finish it—like that was my purpose. Not to sit there and cry over what had happened, but to create. That day was one of the hardest of my life. I could have ended the series right then and there—but I didn’t. I could have ripped up the portraits and given up—but I didn’t. There were so many things I could have done that wouldn’t have made sense. Instead, I did what was right. I finished the portrait and then took a break for a month. For the entire month of December, I stepped away from the series and focused on something different—creating four portraits of the Keystone winners from the inaugural leather contest. The same contest where Duke had been a judge. The same place where we had met.

I want people to understand that I’m not going to quit—I will rise to the occasion. I will persevere through any obstacle that stands in my way. Come hell or high water, I will finish this series with fifteen male models.

I finished the portrait and messaged Duke about doing the interview and photoshoot at MAL since we were both going to be there anyway. He said “yes…” So, I had to wait until MAL to see him again—specifically until Sunday, after the contest, for the interview and photoshoot. In the meantime, I actually had a good time just people-watching. No one knew who I was at first, but once I put on my royal blue leather contest outfit, people started approaching me and striking up conversations about it.

The Interview/Photoshoot

The Reference Photo

Right after the contest ended and Jason was announced the winner, I caught a glimpse of Duke out of the corner of my eye, walking toward the back of the ballroom. I immediately darted over to the back hall, and we quickly took the photo you see here. Then, we headed up to the lobby, to the back of the circular lounging area, where we conducted the interview.

At the time, I wasn’t mad or sad about what had happened—I was more curious about why. Plus, in my opinion, I had developed some really good questions for him to answer. I already knew a lot about his life—his job, his family, and some personal details. I didn’t know everything, but I knew what I needed to at the time. We finished the interview, and then I realized I had forgotten about the hankies—something I had overlooked in most of my interviews. Once I took care of that, I started working on the source material.

The Process

I was excited to work on this portrait, but at the same time, I felt incredibly emotional. Some of the feelings from before started resurfacing. Many artists use emotional energy to fuel their creative process, and for me, it only deepened my passion. I wanted to prove—to the world and to myself—that no matter what I endured, no matter how painful or difficult, I would be alright. I would come out on the other side of this emotional rollercoaster a changed man—and a stronger artist.

The Source

Duke’s portrait took longer than usual—not because of any emotional struggles, but because another portrait project came up. I had decided to start drawing the winners of a new contest moving forward. This would be a way to get my name, Pat The Artist, out there in the community and, hopefully, gain more exposure. Once I finished the two other portraits, I immediately started working on Duke’s crocodile vest. In my opinion, it looks cool, but drawing all the individual scales and shading them correctly was a pain in the rear end—a challenge in and of itself. My original idea was to depict him in a more Western-style outfit, preparing to lasso someone, but I was ultimately satisfied with what I got. It took me two months just to get one usable photo. I was willing to do whatever it took to capture the perfect shot of him. After finishing the leather crocodile vest, the rest of the portrait went smoothly. He only had three hankies—Navy Blue, Hunter Green, and Rust, all on the left side. I had to figure out a good rust color, so I settled on a darker orange—something more luminous, not quite brown. I didn’t have an actual “Rust” color pencil, but I made do with what I had. And honestly? I think it looks good.

The Finished Portrait

“The Cowbear”

11x14 Bristol Paper, Faber Castell Matte Black Graphite Pencils, Faber Castell Graphite Pencils, Ohuho 320 Marker Set, Prisma Color 150 Color Pencil Set, White Posca Pen, Zebra Brush Fine Pen

This portrait is one I will remember for the entire series. There are many others that are great, but I will always remember the journey it took to complete this one. Once again, I want to make it clear to those reading this—I don’t want or need any drama from this. Putting emotions aside, I simply wanted to share the story behind this portrait. Nothing more. Just the story. My hope is to inspire you. When you’re faced with a boundary or obstacle in life, always find a way to push through and get it done. Duke doesn’t need any more drama in his life, so please be kind to each other. If you have any questions about anything I’ve shared, feel free to message me directly—I’ll be happy to answer. I hope you’ve enjoyed both the process and the story behind this portrait. I’ll be starting the next painting in the series soon—so stay tuned!