The year is 2024, and sports betting and social media content are two industries that are notably thriving together. However, when it comes to prognosticating sports, everyone claims to be an expert these days. In an ever-dynamic and competitive world, influencer Kendra Middleton has confidence staying true to herself.
Middleton is a Florida native with a sports media background. Currently, her online following is sturdy at 62K followers across Instagram and X. Despite being a die-hard Jacksonville Jaguars fan, Kendra has made waves throughout the Boston radio scene.
If you’ve been in New England and not heard her on 98.5 The Sports Hub, you racing fans have likely seen Kendra hosting on F1 Arcade, which is Formula One’s social arm. Still, it is her sports betting content from her own channels that has garnered significant steam as of late.
And with gridiron season here, there was no better time to talk with Middleton. Prior to the NFL regular-season opener (Chiefs vs. Ravens on Sep. 5), Playboy’s Gabriel Santiago chatted with Kendra on all things football, sports media, staying true and hanging with David Oritz.
Playboy: Let’s start at the beginning. Tell me a little bit about your upbringing. What’s your origin story with sports?
Kendra: I’m from Jacksonville, FL—born and raised. I moved all over the country since then, but I was in Jacksonville for the majority of my childhood. The Jaguars started in 1995 and I was born in winter of ‘96, so it was kind of just destined to be Jaguars fandom for me. When I was born at Baptist Hospital, they actually put me in a Jags onesie. I don’t think you can really bail after that. The 2017 AFC Championship game against the Patriots was kind of the craziest night of my life. Also, my brother played football for Navy. So, I grew up in a football household but with all sports. Being from the south, football is kind of bread and butter. There were no TV shows, no movies, it was sports all the time. It didn’t matter if it was curling or the Little League World Series.
Playboy: Care to share a specific family story?
Kendra: My dad had been in a fantasy football league with his same friends for 20 years and he and my brother had done it. My brother left for college and I asked my dad, “Can I please come to your fantasy football draft?” He had literally never won it. Well, he let me help him with his draft and that was the first year he won his fantasy football league. Another time, I won my mom flowers for Mother’s Day by calling in to a sports radio show and answering soccer trivia correctly. I was maybe in sixth or seventh grade, so that was kind of my “I can work in sports” moment.
Playboy: You grew up in Duval County, FL, which is obviously a football hotbed. As someone who was raised in the Sunshine State, what drew you to go to school at University of New Hampshire?
Kendra: So, I started at Auburn because I thought that SEC was always the dream. I actually deferred college for two years to intern out in the Bay Area with a sports radio station. Then, I wound up following Grateful Dead for a little bit because I had some time between when I started college and my internship ended, but the SEC was always the dream. I didn’t want to go to the University of Florida because I didn’t want to be close enough for my dad to just show up unannounced. But I wanted the SEC experience and Auburn was really the only school that spoke to me. Eventually, I had enough of living in Alabama. And I knew the Boston sports market. Boston sports radio is just the best in the country and has been for quite some time and UNH offered a really, really great FCS football program, they had a great hockey program. Also, you’re close to Boston and all the New England sports stuff. It was one of those situations where I wanted to get my foot in the door before I graduated because there’s really not a whole lot to offer as far as media relationships and that kind of stuff in a smaller town like Auburn, AL.
Playboy: What’s the best quirk about Fenway Park?
Kendra: Pesky’s Pole. It’s the section of seats where — unless you know Fenway Park, do your research or click the seat-view option on the ticket website — you can’t see the field at all. You’re literally sitting behind a pole. Sometimes, people come to visit Fenway and they buy those seats by accident because they’re always available; that’s really funny. Also, the Red Sox mascot Wally. If you see him, ask him to play rock-paper-scissors. He sucks at it.
Playboy: Understood. It’s on, then. Switching gears here. Throughout your sports media career, do you have a favorite person you’ve interviewed so far?
Kendra: David Ortiz — no question about it. Ortiz is obviously a legend, not just in Boston, but in sports in general. I’ve been lucky enough to have the opportunity to work with David Ortiz. There’s the saying, “don’t meet your heroes,” which I wholeheartedly agree with 99.9% of the time. There’s been a lot of athletes that have been great and a lot of athletes that have been disappointing. But any nice thing that anyone says about Ortiz, I swear it’s true.
Playboy: That’s very believable. Let’s move over to the sports betting conversation, which is a burgeoning industry in the United States. Can you describe your methodology in researching your football picks?
Kendra: First, looking into trends. Second, not overthinking anything. I feel like there are so many people who get too caught up in numbers that they forget to feel the vibe of a situation. Yes, your gut will lead you astray sometimes, but as long as you use at least the “two halves of a whole idiot” situation by finding harmony between your brain and your gut… I feel like that’s when you are a little bit more successful. Also, playing favorites isn’t bad—especially this year. In 2024, it’s been a year for the chalk. And in gambling, it’s not so much about being square or whatever. It’s about being square at the right time for the right price.
Playboy: In this hyper-competitive space, what separates you from other sports betting creators?
Kendra: I don’t want to throw shade, but I think that there’s a difference between how you present what you have to say. I feel like there’s a lot of women out there who ramble on or think that what they’re wearing or something like that is enough. Yes, one, you need to know what you’re wearing. Two, if you know what you’re saying, people are going to take you at face value.
Playboy: Discuss what it’s like to navigate this male-dominated space.
Kendra: If you’re a woman in this industry, you do what you can to generate clicks and there’s nothing wrong with that. If that’s what you want to do, go for it. I wish more girls would make picks in bikinis because my timeline would be 10 times more lit. But as far as separating yourself from the guys, anytime I walk into a room, or anytime I post on X, anytime I’m on the air, anytime I do anything, I feel like me and all the other women in this space have to know 10 times more than any guy in the space because we’re going to be questioned 10 times more often. So, if you want to go out there and post your betting picks in a bikini, do it girl! But make sure you’re doing your research. And I think that that’s the big separation. Really, it’s about what you know and how you present your product.
Playboy: Well said. So, with opening night almost here, which of the four NFL Week 1 primetime games are you most looking forward to having action on: BAL at KC, GB vs PHI, LAR at DET or NYJ at SF?
Kendra: I’m most excited to get in on the Green Bay and Philly game in Brazil. The Packers are obviously super young and on the come up. I have a lot of faith in them. Although I understand the market and getting ahead of it, I thought the Jordan Love contract was a little insane. Love’s been rumored to be struggling a little bit in preseason and camps. I am leaning Eagles pretty heavily here. Philadelphia’s drafting the past couple years has been really good. It’s Week 1; everyone is super healthy. If this were later in the season, I might feel differently because we don’t know where we would be, but I’m going to wind up taking Philly to cover.
Playboy: DraftKings Sportsbook has Patriots QB Drake Maye listed at 13-to-1 to win AP OROY while showing 10-to-1 odds to lead all 2024 rookies in regular season passing yardage. Do you think there is value on Maye in either market, and if not, who?
Kendra: Absolutely not! Hell no. No. Who’s Maye throwing to? Demario Douglas? Ja’Lynn Polk has looked really good in the preseason. I’ve been listening to these press conferences like crazy. I’ve watched all the preseason games. I’ve gone to training camp. I covered this team super closely. The first thing is this offensive line is one of the worst offensive lines I have seen in my 28 years of watching football and I truly mean that. Jacoby Brissett is starting and I think that he’s starting because the Pats are so scared that this offensive line is going to get Maye “Joe Burrowed” if they throw him out there. I think that’s the worst thing you could do for Maye’s confidence. I’m worried that they’re going to do “Mac Jones 2.0” to him. You didn’t go out there and get an offensive line. You didn’t go out there and get receivers. You have all this cap money and you’re not helping the kid out. Unfortunately and in my opinion, with this offensive line, Brissett is going to wind up taking a gnarly shot at some point. Is that what I want to happen? No. But watching this offensive line the way that I have, I just don’t see how it doesn’t happen. But from a betting perspective, there is no value on Drake Maye’s board. I get that the obvious answer is to chase Caleb Williams but I believe in voter fatigue. Williams is the favorite, a former Heisman winner and the first overall pick. I feel that narrative will follow him. Moreover, I like Jayden Daniels and Bo Nix here.
Playboy: Patrick Mahomes and the Kansas City Chiefs are attempting to make history by winning three consecutive Lombardi Trophies. Prior to Week 1, K.C. is the favorite to three-peat at Super Bowl LIX. Is there another team you are betting on in either market to stop the Chiefs’ title streak?
Kendra: Yeah, I actually have the Ravens believe it or not. It’s not that I think the Chiefs can’t, but it’s just silly for me to assume they can three-peat. I get that they are a juggernaut, there’s no denying. But that just feels absurd. K.C. made some really good moves this offseason like locking up Chris Jones, dealing L’Jarius Sneed for roster space, and most importantly in my opinion, drafting Xavier Worthy. For me, San Francisco has too many mouths to feed, whereas with the Ravens, I think they have the talent but it feels a little more selfless. I do think we’re going have a 49ers-Ravens Super Bowl. At the end of the day, I do think the AFC will prevail.
Playboy: Let’s try to draw a connection between musical genres and betting on different sports. You tell me — If NFL betting is like pop music (everyone does it and it produces the majority of revenue), then betting on what sport can be compared to what musical genre?
Kendra: I am a huge premier lacrosse bettor. I’m a huge Formula One gambler—something quirky and different. I feel like if you gamble on one of these really obscure leagues like Japanese baseball or something like that, you can kind of compare yourself to the indie music of gamblers, right? It’s hard for bigger sportsbooks. They don’t really know how to book it. The payouts can be super well but you have to do it right, and you have to know it well enough to do it. I think that any music people initially are like, “That’s weird. Why are you into that? All this sad music all the time. There’s weird chords and stuff like that.” Us people that enjoy our smaller, more niche betting can definitely get into the more Indie music side of that.
Playboy: Shifting over to college football, it should be an interesting year on account of an expanded playoff field and several universities changing conferences. With the 2024 season freshly underway, are there any CFB futures that have attracted your betting interest?
Kendra: Yes! I am in on everything Ole Miss. I have Jaxson Dart for Heisman and I have Ole Miss to make the CFP. Mississippi retained a lot of their guys. Lane Kiffin rocks. He clearly believes in Dart. Kiffin had success at Alabama, success at FAU. And now he’s at Ole Miss. As far as an SEC schedule goes, theirs is kind of a walk in the park. The Rebels don’t play Texas, they don’t play Alabama. Also, I love a quarterback who’s been to two schools. Dart is a dual-threat player. He had eight rushing touchdowns last year.
Playboy: Summer is coming to an end and the 2024 Fall Classic will be here soon enough. Who do you like to win the upcoming World Series?
Kendra: I’m not the biggest baseball gal but I hate the city of L.A. and I hate the Yankees because I’m cultured. I’m rocking with the Phillies. They’re a fun team. They have the bats to do it. I think they have a pretty selfless roster. I know people have a lot to say about Bryce Harper, but I think that these guys really love each other. They gel really well. And once again, the value is there for me, so I know you shouldn’t bet with your heart, but I’m really chasing the Phillies this year.
Playboy: Can we count on seeing you at F1 Las Vegas?
Kendra: I’m actually coming to Vegas for the Raiders-Jaguars game. Because I work hosting all of the events for Formula One at their location in the States, I don’t have a ton of time to get out to the races. But if it is an off week for that, then I might be out there.
Playboy: What’s a day in the life of Kendra Middleton look like right now?
Kendra: I know that people love to think that working in sports is this big and glamorous lifestyle, which it is. I wouldn’t change it for anything, but eight months out of the year, you’re working seven-day weeks. It’s a lot of research. I have an Australian Shepherd who is absolutely nuts, so we do a lot during the day time. I wake up, walk the dog a couple miles, have a coffee and then I’m in front of my computer doing research until I decide to make dinner. At night, I’m filming at events, restaurants or any kind of openings in town. I’m pretty much seven days a week on the constant grind. I don’t hate my job, so it doesn’t really feel like work to me. I genuinely can’t complain. I eat a lot of good food, I meet a lot of cool people and I have a kick-ass dog. I also love to lift weights; I do that about six days a week. I work a lot with Formula One arcade as well, hosting their watch parties. I don’t want that to end, but Sundays are about to be crazy for the next few months.
Editor’s note: The advice provided by the author does not represent the views of Playboy. Taking any advice will not guarantee a successful outcome. Always use your own judgment when participating in sports betting. Still, for daily bettors, the best insight anyone ever gave me was to stay away from parlays.