In the 14 years of the APSE Diversity Fellowship, we’ve grown accustomed to watching the Fellows go on to do great things. But we’ve never seen one go on to do great things on “Wheel of Fortune.” Now we have.
Damon Sayles, a member of the 11th Fellowship class, not only made it onto our TV screens, he also dominated. Damon was the big winner on the Nov. 20 episode, solving the final puzzle and winning the $10,000 Triple Toss-up and a trip to Barbados on the way. How good was he? After collecting the million-dollar wedge, he had a chance to win the $1 million Jackpot at the end. Unfortunately, his final spin didn’t land on the million-dollar envelope in the bonus round. He walked away with $69,290 (take out taxes). Only four people have ever won the $1 million grand prize.
Damon is back doing impressive things as The Athletic’s Culture editor, but he may forever have a hard time topping his clutch “Wheel” performance. Now that the excitement has died down and he has returned to being a ho-hum sports journalist, we caught up with Damon to ask about his brush with fame and his life in general.
How did you get on “Wheel of Fortune” and what was your inspiration? Had you been on a waiting list? All credit goes to my wife, Jennifer, for getting me on. This was a tribute to my aunt, Beverly, who passed away in January 2024. She and I would watch two shows when I was a kid: “Mr. Rogers’ Neighborhood” and “Wheel of Fortune.” We had her funeral on a Saturday, Feb. 10. Two days later, my wife and I watched “Wheel,” and I was red hot. I solved puzzle after puzzle. After the show ended, I looked to my wife and said, “God, I miss Bev.” I briefly went downstairs, then came back upstairs. My wife was waiting on me with her phone. She told me to say what I was saying while the show was on. Basically, she wanted me to talk about my aunt and how important she was to me in relation to “Wheel.” I went along with the idea not thinking anything of it. Little did I know, my wife used that video as an audition tape. She submitted it, and the “Wheel” reps got back in touch with me. After a few months of going through an interview, then playing a virtual game with them, they told me that they wanted me in California for a live taping. The rest is history.
How was the experience on the show? Unbelievable. It still feels like a dream that it even happened. I found out that roughly a million people apply to be on the show. To me, this was something of a lottery win. What made it even more memorable was winning for my aunt. I told myself if I solve one puzzle, then I’ve done something good to honor her. I ended up solving 8 out of 10 puzzles, won a trip to Barbados and earned an additional $40,000 in the bonus round. And because I landed on the Million-Dollar Wedge, I nearly became a millionaire. Almost.
What has been your experience afterward? I also work at The Athletic, so I KNOW you are a celebrity there. Any keys to the city? Have a lot of childhood friends, college pals and distant uncles reached out to congratulate you? A lot of congratulatory words, a lot of “Let me borrow some money,” a lot of new random social media friends. It’s all funny to me, but I just remain humble, thank God and keep moving forward. Those who know me know that because I’m introverted, all of this makes me slightly uncomfortable, but they also know that I know how to turn up my extroversion when necessary. Honestly, this has all been a wonderful experience. I’m so grateful.
You were in quite a zone (too bad you didn’t win the million). And you showed yourself to not only be a great puzzle-solver but also a great vowel-buyer. How did you get so good? I got good by watching the show for so many years. This show has been a part of me for more than three decades. I keep telling people that I hope my aunt was proud. I know she was looking over me. As for being “in the zone,” I remember once scoring 35 points and making eight 3-pointers in a basketball game. I felt like I couldn’t miss. After this “Wheel” experience, I realized I wasn’t “in the zone” then. I was definitely “in the zone” in front of Ryan Seacrest and Vanna White. I told my wife after watching the broadcast for the first time that I didn’t remember about 75 percent of the show … and that’s the truth. For 22 minutes, it felt like I couldn’t miss. I’m just glad it happened when it happened.
Stardom aside, how is life? What’s the latest with you personally andprofessionally? Life is great. I wouldn’t call it “stardom,” but I really do just appreciate everything that this experience comes with. People have asked all kinds of questions: “Are you going to quit your job now?” I didn’t make enough to quit my job, and even still, I wouldn’t quit where I love working. “Were you on ‘Jeopardy!’?” That one’s funny to me. A funnier one: “If I make it to ‘Family Feud,’ will you be on my team?” People are funny, but again, I just take this all in stride and remain thankful. God didn’t have to put this in my life, but he did. I’m going to take care of my daughters and their education, buy a couple of necessary things for the family and then maybe take my family on a trip. Of course, the trip to Barbados will be me and my wife only, and she’ll get whatever she wants.
What are your memories from the Fellowship experience? My Fellowship experience was tremendous. It helped me so much as I’ve transitioned from writer to editor. I am a much better editor because of the tutelage received. I’ll always remember the times spent with my “fellow Fellows,” as I like to call them. It’s good to see them excelling, as well. (Shout out to Meredith Perri, Zach Powell, Patrick Bernadeau, Kelly Ward and Alex Vejar.) I like historical facts and markers, so knowing that I was a part of the first class to graduate three Black men (along with Zach and Pat) always will hold weight. Class XI forever will hold a special place in my heart.
What advice do you have for APSE Fellows regarding their careers, whether in media or any other vocation? There is no such thing as skating by if you’re truly trying to be successful — especially in our business. You must be truly ready to work. You need to be hungry. That said, you also have to accept criticism and learn from what’s been told to you. If you’re hearing positive stuff all the time about what you do, are you ever really learning or improving? At The Athletic, I’m so fortunate to have a support staff that will congratulate me when I do right but immediately let me know when I mess up. For me, it’s all about being better than I was the day before. You’ve got to have that mindset in order to succeed. Also, and I tell this to everyone I speak with: Treat each week like it’s a seven-game series in the NBA, NHL or MLB. If you can win four days out of a seven-day week … that’s a good week. If four is good enough to win a championship series, then it’s good enough to advance to the next week with a smile on your face.
Was there any great help or mentorship you received from someone in sports media? I’ve received so many good tidbits from people I truly respect in the business. Lisa Wilson has been the most honest with me. She doesn’t realize how much I value her. She sees my potential, and she pushes me — whether I want to be pushed at the moment or not. Leon Carter has been a great person to where we trade stories all of the time. I hope he understands that while I’m listening to him, I’m also hearing him (big, big difference if you digest that properly). Michael Anastasi was a guy I chatted with early in my time as a Fellow, and I picked his brain and got some valuable tidbits. Barry Bedlan has been one of the funniest guys of APSE, but his mind is sharp, and I enjoy everything that he brings to the table. Sergio Gonzalez has shown me how to be a tough-but-fair manager. More managers should be exactly like him. Rick Mann, Doug Pils and Cameron Maun were among my first editors out of college, and they are valuable assets and true reasons why I continue working in journalism. The list can go on and on for me.
Photo credit: Top image courtesy of Sony Pictures Television; Photographer: Eric McCandless