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Holding Court and Making History With WWE Queen Charlotte Flair

Last Updated: July 1, 2023
The sports entertainment icon talks smashing milestones in the squared circle, dreaming of a Hollywood crossover, navigating investments and endorsements, and fellow superstar Bad Bunny.

Charlotte Flair is a 14-time world champion in the pro wrestling ring with more critical plaudits than a Paul Thomas Anderson film and more athletic feats than a night of Tony Hawk’s Pro Skater. As a trailblazer for women in the squared circle, she owns more firsts than the Oklahoma City Thunder. And though her exploits as a “Grand Slam” champion in WWE stand alone, this business is very much a family thing for Charlotte, North Carolina’s queen.

Her father, the inimitable “Nature Boy” Ric Flair, is an all-timer of the highest order. Her brothers were in-ring performers. Her husband, Andrade “El Ídolo,” is a former WWE belt-holder now flying high with AEW. None of them, however, can match Charlotte’s seven appearances at the most prestigious event in sports entertainment, WrestleMania — the latest of which was a bang-bang classic against Rhea Ripley on April 1 that left the jaws of the world firmly placed on the floor.

Naturally, on the heels of WWE’s acquisition by Endeavor, we had to seize the opportunity to speak with her about her groundbreaking career, the evolving state of pro wrestling as a family business, her thoughts on crossing over into Hollywood, and more.

Check out Boardroom’s conversation with Charlotte Flair below, edited for length and clarity.

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SAM DUNN: You just had a huge championship match at WrestleMania 39. WWE just sold to Endeavor. A lot is happening all at once — how are you doing with all this?

CHARLOTTE FLAIR: When it comes to the business side, I feel as a performer, my position isn’t gonna change. Maybe if I was brand new, but my job as a performer is just to make who’s behind the headphones and gorilla happy, and then the fans. I don’t really get wrapped up in what’s happening there, but the sale is a big deal. I’ll be interested to see what happens in the future with Endeavor.

For me, I went from having never any off-days to getting injured last year after WrestleMania and being off for seven months, and then now off again for a couple weeks for something that I needed to take care of, so it’s a blessing and a curse. Like, no one wants to be injured, but having that first time off for that extended amount of time, I think was definitely healthy for my mindset.

SD: When you’re away from that daily grind like this, do you find yourself eventually getting restless?

CF: I like action, to be honest [laughs], But after a month or two, I was like, okay, what am I supposed to be doing? This isn’t fun. I had too much time to think.

SD: You’re coming off an eye-popping showdown with Rhea Ripley for the SmackDown Women’s Championship at WrestleMania. When something big and resonant is happening in that ring, do you feel it?

CF: Let me think about that. Well, at this point in my career especially, that was my seventh WrestleMania, and at all seven I’ve either been the challenger or the champion, and that’s never been done. So, experience-wise, I’m able to go out there and enjoy it; before, I was never in the moment. As time goes on, you get more comfortable, so I was like, yeah, I need to make this memorable. We need to show them why we should have been the main event, that the women can tell stories just as good as the men, work at that level and rate and professionalism.

As a viewer, you will forget the gender as you’re watching us. Not just a good match; it needs to be one of the best matches of the weekend, so I knew that I could do that with Rhea. I had that confidence going out there.

SD: What else was different about this WrestleMania compared to all the others you’ve experienced?

CF: This was a different role, too. Like, I’m usually always the bad guy. But in prior years, I didn’t have that edge or I didn’t have that knowledge to still play that role and do my job and not have some of those “Flair-isms,” like [for] the heel-ness and the bad guy in me to come out. It was my job to portray [Rhea] as the big guy, the dominant guy, the evil one [laughs].

SD: What is Rhea Ripley’s particular energy as a WWE superstar? Just placing the two of you side-by-side, that juxtaposition feels like a fascinating narrative by itself.

CF: I find it as a challenge — and that’s what I was so invested in, the challenge — because it’s easy for me to just go out there, be an arrogant you-know-what. Rhea’s character isn’t necessarily arrogant; it’s edgy. It’s cool. She’s not a heel. You want to portray her as a star; you don’t want to label her as a good or bad guy.

Knowing that, I could make that come to life was such a great challenge for me as a performer and where I’m at. That’s when it gets fun, I’m outta my head just changing some of the things up that I would naturally do in a match. It was a great challenge; I don’t know how else to put it without giving away the magic [laughs].

SD: For a match like that, did you find yourself applying any lessons from your legendary scrap with Becky Lynch and Ronda Rousey at WrestleMania 35 in 2019?

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CF: No, totally different situation story-wise, level-wise. We were so hot going into WrestleMania 35 — that story between me, Ronda, and Becky on that Raw when the police were there pulling us apart and fighting backstage I mean, it was wild. Totally different.

The only thing I take is just from being on the big stage so many times. It’s our Super Bowl. So, technically I’ve been to the Super Bowl seven years in a row. My dad loves sports, so he’d be like, ‘You’re like my Tom Brady.

SD: I’m glad you mentioned your father, because pro wrestling has this distinctive aura as a family business. The McMahons have been in this for four generations now. Even with the Endeavor deal, it’s got this unkillable familial spirit.

CF: Why is that? That’s wild. I never thought of it that way. The only thing you’re seeing now more — father-daughter combinations, maybe. You see a lot of lineage with the males, but the father-daughter dynamic is still somewhat new. I don’t think that’ll ever go away; I think you grow up wanting to do what your father does or your mom does.

I mean, I didn’t necessarily, but my brothers did. They wanted to do exactly what Dad did. I just ended up somehow doing it in my late twenties, and here I am [laughs]. It was not casual. I don’t know why it’s in the family. Maybe because it’s so unique.

And the women are viewed differently now, so it’s even more like, ‘Oh, I can, I do have the opportunity to do that.’ Not just be eye candy, a secondary storyline, a valet — like no, the women are doing it, and there’s so many schools. Different organizations. It’s all over the world. It’s the one sport that everyone can understand. Good versus bad, and you don’t have to speak the same language. Good guy, bad guy.

SD: Who are some of the women in the business over the years that you most remember watching and enjoying?

CF: I have to be honest, I did not pay attention to the business growing up at all. Like, it was cool to see my dad wrestle, and when they came to Charlotte — because I grew up in Charlotte, North Carolina — my high school senior year, I went to the show where Trish Stratus and Lita main evented Raw for the very first time. It was wild. I was sitting front row for that. So then, exactly 10 years later, the second-ever [women’s] main event of Raw, it was me versus Sasha Banks. So, oh my gosh, maybe subconsciously something was going on. Destiny, fate, I don’t know, but knowing that they did that and sitting front row going, ‘Well, okay, I could do that athletically.”

I’m competitive, but I never saw myself as a show woman or a Diva at that time. I just couldn’t put myself in their shoes athletically — I could, but not on the scale of how they were presented, but then knowing that Sasha and I did that 10 years later exactly. And then I went on to be the first [women’s] main event of a pay-per-view, the first main event of SmackDown, WrestleMania, the first-ever TLC, Last Woman Standing, I had the opportunity to go on to be the first of so many after sitting in that front row. [You] keep that momentum going to where one day, when the girls are main eventing, you don’t go, ‘Oh, they’re main-eventing.’ There’s no more ‘first,’ it’s just a regular thing.

I’m not saying that we don’t have to fight for our spot. I feel like we have to fight a little harder, but it still happens.

SD: With that in mind, knowing you’ve really got an incredible record of accomplishments in that squared circle, is there any bucket list stuff you still want to do in the business that you haven’t had the chance to do yet?

CF: I think now, it’s just getting to that next level. Like, I know that my name is popular within sports entertainment, but I wanna get to that male level of John Cena, The Rock, Batista still. I want to cross over like my dad has so gracefully, and I’ll continue to do that until I get to that point. I hate that I started so late in the game, but I’m here. I think that’s just a matter of time.

SD: You mentioned Sasha Banks, a.k.a. Mercedes Varnado. She’s in the Star Wars universe now on The Mandalorian, which is incredible. What sorts of opportunities do you envision for yourself in Hollywood?

CF: I’d say for the first time in 10 years, I feel like I’m in that spot now where I can look outside the box. I wanted to do all these things and nothing else mattered. Now, okay, I accomplished these. I’m more comfortable, so now, it’s putting myself in positions where I’m not as comfortable. Seeing what happens, what that will look like, whether that’s auditions, where do I fit in what roles, absolutely. Sports entertainment is my home, but [it’s] seeing what I can take from what I’ve learned in the ring elsewhere.

SD: Those big names you mentioned are all attached to at least one huge IP. The Rock has the DC universe and the Fast franchise. Dave Bautista has Marvel. John Cena has DC. Is there a blockbuster property that would be a dream for you? Like, the Game of Thrones world or something like that?

CF: I just want to keep an open mind. It took time for all of them to get to that spot, so for me, it’s just what’s gonna come my way will come my way. I mean, Game of Thrones is awesome [laughs]. I don’t want to limit. I’m up for all opportunities.

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Honestly, I don’t have a dream. Like, I didn’t have a dream going into wrestling. I don’t have a dream making this transition, it’s just taking what I’ve learned and all these opportunities and seeing what else I can do if I just put my mind to it. I don’t know what’s next. I just know I wanna take what I’ve tried to do for women in this industry and help keep pushing forward with that.

SD: While you’re exploring who and what Charlotte Flair the action star could truly be, what can you tell me about Charlotte Flair the businesswoman? Who is Charlotte Flair the investor?

CF: I’m very selective. I think I’ve watched my dad go up and down, up and down on different endeavors or investments throughout the years. I think besides the homes that I have purchased along the way in North Carolina and Florida — real estate has been the most effective, the most safe, easy for what I do — but moving forward, I’m kind of looking into what that next investment looks like.

Unless I’m working with a big brand that’s already established, I’m very conservative when it comes to investing in these ideas. I’ve seen all these crazy ideas come to my dad over the years for, like, the last 20 years. He’s attached his name to so many things, and who would’ve thought marijuana was the No. 1-selling thing as of now in 2023, the “WOOOO Chews”? But no, I’m very cautious when it comes to attaching my name to anything that I don’t necessarily believe in.

I’ve worked with Girl Up, an amazing organization for gender equality. Special Olympics, I’ve been with them since I started at WWE. Be a STAR, the anti-bullying campaign. I’ve worked with Cricket Wireless, I’ve done a Snickers commercial, I’ve done Burger King. Those are solid brands that everyone knows that are family-friendly, they’re known all over the world.

SD: Is there a dream brand you haven’t worked with that you’d most like to have as a partner?

CF: Rolex, a hundred percent. Rolex, Range Rover, Nike. Those would be dream endorsements.

The tradition with Rolexes in sports entertainment; once you’ve main evented, you get a Rolex. My mom and dad gave me my first watch when I got my scholarship for volleyball, and then this [points to her wrist] is the watch that Shawn Michaels gave my dad when he retired. So, when I main invented my first pay-per-view, he gave it to me. All the world champions have one usually in WWE, so there’s, like, a little story with it.

SD: Not for nothing, the Flair family has been name-dropping Rolex for a long time.

CF: To represent a brand, you want it to be 100% authentic. People see through that so much.

Project Rock, I think the only female who’s done it is Lindsey Vonn. I think that would be cool. Those are just the ones off the top of my head that are major, major brands. I travel a lot, so anything with Marriott [laughs]. A major gym franchise like Gold’s Gym back in the day would be up my alley. I partnered with Pure [Life] Nestlé before, a water campaign, and any kind of supplement line. A major supplement line for your basic needs for athletes.

Actually, my husband and I for a while were like, ‘Let’s come out with our own hot sauce!’ [Laughs] Yeah, that was a real thing.

SD: I do have one thought about Nike. I don’t think there’s ever been an athlete in pro wrestling with a signature shoe deal like basketball players get, so the “Nike Air Flair” is just waiting to be done.

CF: That sounds amazing. “The Woo Shoe.”

SD: The Woo Shoe!!! That works on multiple levels.

CF: Absolutely. To have the Nike swoosh on my wrestling boots — the Woo Boots.

SD: The brand exposure value for something like that at a pay-per-view show in a full stadium would be off the charts.

CF: That makes me think of Brock Lesnar when he wore a Jimmy John’s logo on his wrestling trunks.

SD: Looking ahead to this weekend, the WWE is headed back to Puerto Rico. There’s such a wrestling history there, including some exciting moments your dad was a part of, and it’s a whole new ballgame with Bad Bunny on this incredible ascent. Do you have any particular thoughts about what that all means?

CF: We actually had a live event in Puerto Rico right when we went back on the road in the summer of 2021. We were in Puerto Rico that fall and the reception was incredible. Wrestling is so big there. It’s one of the old territories. Having Bad Bunny, with him being such a pop culture star right now, it just makes it even more special that he’d wanna be a part of what we’re doing. A crossover with the music industry, I think, is exciting. I’m a little jealous that I won’t be in Puerto Rico for this. I’ve also told Bad Bunny at any time he needs a tag team partner, I’ll be his tag team partner [laughs].

I think it’s exciting. I think it’s great. I think goes to show how big WWE is.

SD: WWE performers have moved into showbiz and become massive global stars, but San Benito is already the most-streamed musical artist and he’s coming into WWE. Who’s ever done that?

CF: And he loves it. You can tell he respects the business, he loves the business. He works really hard and I don’t think he’d be where he is in his industry if he didn’t have the ability to adapt. Our business is not easy, and you could tell how much he loves it and wants to be [here]. He wants to be good at what we do. It’s very admirable.

SD: He’s legitimately good. I think it was The Miz who said one time that Bad Bunny was out here trying and landing moves that he himself wouldn’t have attempted.

CF: It’s just unbelievable how much he’s thrown himself into the sport and wants to be good at it. You don’t see that many people who come from different industries putting that much time into it, and he does.

I know it’s cliché, but it’s inspiring to see someone from another industry and what he can do in a different one, so that’s like me. I’m like, ‘Slowly but surely, I’ll get there.’ Not singing, though, that’s for sure [laughs]. I cannot sing.

SD: How about getting you in a music video, though?

CF: I’ll take a music video. I’ll be the backup dancer.

SD: Okay, let me make some calls. But before I hit up Conejo Malo on his direct line he doesn’t tell anyone about, any parting thoughts as we wind down?

CF: Just if you’re not a fan or [don’t] know anything about sports entertainment in the women’s division, they are a must-watch. Check out a live event. I always say, if you’ve never watched wrestling, the best thing to do is go to a live event because they’re a lot more relaxed and you get to interact more with the talent versus watching Raw or SmackDown on TV. If you have no idea what to expect, go to a live event, because trust me, we’ll be in your city. We’re there all year round.

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About The Author
Sam Dunn
Sam Dunn
Sam Dunn is the Managing Editor of Boardroom. Before joining the team, he was an editor and multimedia talent for several sports and culture verticals at Minute Media and an editor, reporter, and site manager at SB Nation. A specialist in content strategy, copywriting, and SEO, he has additionally worked as a digital consultant in the corporate services, retail, and tech industries. He cannot be expected to be impartial on any matter regarding the Florida Gators or Atlanta Braves. Follow him on Twitter @RealFakeSamDunn.