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Famous Wrestlers Who Have Crossed Paths With Gambling

By Kendall Jenkins on 2025-10-16 10:25:00

The world of wrestling and the gambling industry often intersect. They are connected by famous personalities, risk, and emotions. In this article, we will talk about famous wrestlers who have collaborated with the biggest gambling companies, tried their luck at the tables, and participated in casino promotions.

John Cena

In 2024, John Cena starred in a commercial for FanDuel, a massive American sportsbook and mobile sports betting app.

The video “Kick of Destiny 2,” featuring John Cena and Rob Gronkowski, was part of a Super Bowl campaign. Fans could make predictions and take part in the prize draw through the FanDuel app.

That wasn't really a casino advertisement but rather a legal betting promotion. For now, Cena still openly cooperates with brands that work in the gambling field.

The Undertaker (Mark Callaway)

The press has repeatedly reported that The Undertaker placed bets on sporting events. In particular, there is a well-known case when he and Vince McMahon bet on the outcome of a football match.

The other time, he, together with another famous wrestler, The Godfather (Charles Wright), lost around $50,000 each in a casino in one night. 

At the same time, there is no official confirmation that Undertaker advertised no verification casinos or bookmaker brands. You can only find private stories from his life.

Ric Flair

Ric Flair is famous for his love of the high life and is often spotted in casinos around Las Vegas and Atlantic City. He has never been shy about showing off his flashy lifestyle. It’s no secret that Flair is a huge gambling fan.

In December 2023, Flair launched an advertising campaign for his own cryptocurrency, WoooooCoin. It’s not exactly a casino, but the crypto world often crosses paths with gambling. 

He also regularly participates in fan meetings and events held at big-name casinos. One of them is autograph sessions in Las Vegas. But these are more about image than actual promotion of gambling platforms.

Conclusion

Wrestling and gambling go hand in hand. It is all about risk, adrenaline, and putting on a show. John Cena has already stepped into the world of legal betting, while The Undertaker and Ric Flair have long been linked to gambling, whether through their stories or stage personas.

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