I may never understand why CEOs do what they do.
For one, my X-Gene didn’t grant me telepathy. For two, I never foresee myself CEOing anything other than my house and whether someone can or cannot eat in my car.
I may never understand dollars and cents to that degree, but I do understand more dollars stack from doing what makes sense. And letting Westside Gunn cook made all the sense in the world. That WWE reportedly refuses to do so is another sign that their flirtation with Hip Hop culture since the TKO takeover is performative at best and exploitative on the opposite end of that spectrum. If I may speak their language, none of that is what’s best for business.
For the uninitiated, Gunn and his Griselda crew (Conway the Machine, Benny the Butcher) spent years curating a sound that heavily incorporates professional graps. He’s also the reason everyone sings about how they hurt people at the top of their lungs at AEW shows. That’s his voice contributing to one of wrestling’s biggest themes of the moment. It’s not uncommon to peruse his albums and hear cats like Jimmy Hart and Ric Flair contribute. One Google shows him in flicks with Finn Balor, Eddie Kingston, Daniel Garcia, MVP (obviously), and the late great Scott Hall. To say nothing of the numerous AEW and WWE shows he sits ringside for.
Seriously, it’s like playing Where’s Waldo; he’s always there even if he’s not highlighted. And the cherry on top of this wrestling sundae? He’s Hip Hop. That doesn’t mean he’s just a rapper. When someone is Hip Hop it’s about the attitude and cultural aesthetic they embody. It’s authentic — it can’t be bought, borrowed, or faked.
Griselda fans, of which Jay-Z counts himself as one, are birds of that same feather and flock to Gunn and company for that reason. So even if you’ve never heard of the guy, the smart money says your favorite rapper has and is a fan. Gunn’s brand equity is the result of his influences. He wears them all on his sleeve in a way that makes people pay attention.
He may be more “underground” than Doechii or Kendrick Lamar, but Hip Hop culture always bubbles up from the underground. Mainstream rap, despite its sometimes painful efforts, loses its coolness after a while because it becomes manufactured. Rappers on the fringes, like Gunn, dictate the terms of the new hotness because their movements are organic. Fans and musicians alike are drawn to to those types like a camel to an oasis because they want in and want to evangelize. For the better part of a decade, many have claimed to be Gunn’s John the Baptist, including the aforementioned Shawn Carter. So many people laying claim to that title is worth more than its weight in gold. Any members of the culture, even curious onlookers, would get the message and saddle up to ride with rather than ride against.
And then there’s WWE.
Hip Hop is prominent in the company under TKO. Look at everything with Travis Scott, including how for months it seemed like the company believed “FE!N” was the only song ever created. Then there’s Metro Boomin & Cody Rhodes, Migos at Day 1, Cardi B at SummerSlam, and Meek Mill at WrestleMania. They’ve embraced the music in ways not seen since Big Pun told Vince McMahon, The Rock, and The Corporation that he didn’t want to be a player anymore.
But in 2025, it always feels safe. The company goes for the typical artists that don’t require a true love for the culture to know. That’s not diss to anyone they’ve worked with at all, more so an indictment of the company for not digging beyond anyone so ubiquitous that a random dart thrown out of a random window at any random place in the country could hit one of their songs. It doesn’t take love, passion, or even a slight understanding of the genre to hear a Cardi B song, then invite her to SummerSlam. Truly being “down” means going beyond the pop charts.
I know that’s a lot to ask for any Fortune 500 company. They usually aim for safe and middle of the road despite that what constitutes as middle of said road changes by the day. There’s nothing wrong with that if the goal is to communicate a Fugazi understanding of a culture once previously kept at arms length… If that’s your goal. And that’s what it says seems like TKO wants; a grip and grin photo op with chart-topping rappers who show even a modicum of interest in their business. Siphoning brand equity isn’t new, but it’s tragically transparent for a company who goes to exceedingly great lengths to point out which flavor of the month is sitting ringside. Regardless how sweet or sour said flavor is at the time, it’s all good because they have enough cultural juice in the company’s eyes to give it at least a little squeeze.
Now, I understand there’s reported legality involved here. I’m not a lawyer, caveman or otherwise, but I know it’s a bad look when someone uses images and likeness without permission. It’s an even worse look when those images and likenesses show up in a major way. In this world, there are few things more major than a Times Square ad. Heels Have Eyes 3 isn’t the first time Gunn used WWE photos for an album cover, but he didn’t promote those albums on this scale. Literally. Of course TKO and WWE noticed a photo of Ted Dibiase & Virgil towering over citizens like Godzilla. The smart bet was always on picking the billion dollar company to call foul if they weren’t getting any of that action. That doesn’t make their alleged Brooks Brothers Brigade any less shortsighted.
Gunn and Roc Nation (Jay-Z’s label) plastered two WWE legends in the world’s most famous ad space. Yes, to sell his album, but also to do what he’s done for years which is openly promote “the territory”. And for free! All while also positioning it and its past as the coolest thing known to man, woman, or child.
Why not bring him into the fold rather than squaring off against him?
This doesn’t preclude them from asking Sexyy Red to pop up in Orlando either. She and Gunn appeal to different fans. Yet one look at how he and Griselda consistently convince devotees to actually buy their albums rather than just stream says a lot about the following’s purchasing power. Are they all wrestling fans? Can’t say for sure, but they’re not turned off when they see song titles like “Jimmy Hart,” “Ray Mysterio,” or “Undertaker vs. Goldberg.” That last one might be rough for anyone to swallow but that’s beside the point. He thinks wrestling is dope and his fans ride with his tastes.
It’s no different than Wu-Tang Clan creating scores of Shaw Bros. fans simply through incorporating their movies into Wu music. I can’t say with certainty that Shaolin vs. Wu Tang or The Kid with the Golden Arm pop up on my radar without Wu’s help. I can say those movies and others like them filled a void in my life I didn’t know existed. And that’s all due to the Wu. They transferred their allure to flicks far from the tippy top of the pop culture mountain. They shined bright lights artists like Gordon Liu, Lau Kar-leung, and the Venom Mob. The Staten Island crew made 1970s Kung fu flicks relevant for people who didn’t grow up watching them on Saturday mornings or at grindhouse theaters in Times Square. Wu albums provided an emotional connection to bits of dialogue and created new context for the movies.
Even the group’s name comes from those same films; they’re literally a walking, talking promotion for an entire genre. Shaw Brothers, Golden Harvest, and a host of other Asian production companies are still relevant today despite being defunct for what feels like centuries. More importantly for the bean counters and check writers reading this with eyes firmly rolled: they still make money. Shockingly, those filmmakers didn’t clutch their pearls when someone else gave them props and made their creations carry weight for multiple generations who might otherwise show no interest.
Like Gunn, Wu infused another aesthetic into their music to share their love of it with the world. Sometimes it’s as simple as that without any Netflix show, podcast, album or vanity project ulterior motives.
There’s a world where WWE works with a guy with pro sports entertainment in his DNA. That same world sees them benefiting from his profession possibly more than he benefits from their stamp of approval. Unfortunately, that’s not the reality on Earth 1. Their limited view on Hip Hop combined with their bodily reflex to put profit over everything decreased the odds of that ever happening. Not to mention kicking the guy out of an arena in his backyard despite him spending what seems like a king’s ransom on seats.
I don’t know a much about business but I do know the pro wrestling one thrives off genuine connections. Gunn has that connection with not only his fans, but some of the wrestlers inside that same Buffalo arena he was kicked out of. That WWE either can’t see that or choose not to says a lot about how they view the culture and their relationship with it: On their terms and as a narrative they can shape.
I may never know a CEO’s life. But I do know Hip Hop and boy, that ain’t it.
