There are fights, and then there are superfights. Around the late 2000s, Brock Lesnar was the biggest thing in MMA, having made his UFC debut in February 2008. After his big win over Frank Mir in 2009, which saw him defend his UFC heavyweight title, the promotion, particularly Dana White, hoped to match him up with an equally terrifying heavyweight in a superfight. But having dismantled Randy Couture and Frank Mir with ease, the UFC knew there weren’t many heavyweights that could take on the former WWE star, except one—Fedor Emelianenko.

Appearing on The Pivot Podcast, the UFC CEO reflected on the promotion’s unsuccessful attempt to sign the Russian heavyweight during Brock Lesnar’s championship reign, a negotiation he still considers one of the few major fights the UFC failed to make.

“I feel like we’ve gotten everything done that we ever wanted to do in the fight. We never got a deal done with Fedor,” Dana White admitted. “But when me and [Lorenzo Fertitta] got on the plane and left wherever the hell we were, we looked at each other and said, ‘Thank God they said no.’ Yeah, because we offered them so much money.”

According to White, he and the former UFC co-owner personally traveled to negotiate with Emelianenko’s team, determined to make the heavyweight superfight a reality. Instead, they left without a deal. While the financial side of things held up their signing of Fedor Emelianenko, the MMA legend also had a running contract with Strikeforce at the time he was approached by White and Fertitta. Despite this, they tried to make the superfight a reality.

“You know, you get in that room, and you’re just trying to get the deal done,” the UFC CEO recalled. “We didn’t fly all the way the f–k out here for nothing. Let’s get this deal done, and we wanted to do it. We wanted to do him versus Brock Lesnar at the time. But nah. I don’t regret it. And that’s really the only fight off the top of my head that I can think of that we didn’t make that we wanted to and that we tried to.”

Years later, however, Dana White appears to view the failed negotiations with far more perspective. Though Fedor being signed to Strikeforce prohibited them from signing him, the UFC did eventually buy the San Jose-based MMA promotion in early 2011. However, by then Fedor was already fighting in a few different promotions like M-1 Global and Dream. And by then, even Brock Lesnar had lost his heavyweight title.

White’s latest comments also contrast sharply with his public stance at the time. After negotiations collapsed in 2009, the UFC CEO openly criticized the Russian for declining the offer, accusing him of avoiding the sport’s toughest competition.

“Fedor is a f—ing joke,” he said in 2009. “He turns down a huge deal and the opportunity to face the best in the world to fight nobodies for no money!”

In another text to Yahoo! Sports’ Steve Cofield the same year, the UFC CEO confessed, “I feel sorry for the real fans! I wanted to make the deal but it takes two and it is very obvious Fedor doesn’t want to fight the best and doesn’t give a f–k about the fans.”

Sadly, within a few years things had changed. After Brock Lesnar lost to Cain Velasquez and Alistair Overeem, he returned to WWE, and the urgency to make the fight also dissipated. 2011 also saw Fedor Emelianenko lose two consecutive fights, including one to former UFC middleweight Dan Henderson. As such, one of the biggest what-ifs in MMA remained just that. And Fedor retired in 2023, having never fought in the biggest MMA promotion in the world.

The fight has since become one of the sport’s biggest “what ifs.” But this isn’t the only superfight he was unable to make.

Dana White wasn’t always this diplomatic

The first one that comes to mind is Jon Jones vs Francis Ngannou. Back in 2020, when Francis Ngannou was at the cusp of clinching the UFC heavyweight gold, and Jones was already the light heavyweight champion, Dana White tried to convince Jon Jones to move up and fight Francis Ngannou. However, this time around, too, the discussions went nowhere, and things got held up for the same reason: money.

“[Jon Jones] told my lawyer he wants what Deontay Wilder was paid,” Dana White said back in May 2020. “I think it was $30 million was what Deontay Wilder was paid.”

Since the UFC was not ready to pay up that much, the fight never happened, and Francis Ngannou went on to clinch the heavyweight gold the very next year by defeating Stipe Miocic. Coincidentally, though, Jon Jones did eventually move up to heavyweight in 2023. However, by then Ngannou had already had a falling out with ‌the UFC and had left the promotion, giving rise to another superfight that never happened.

There have been a few such fights over the years that have suffered this exact fate: Georges St-Pierre vs Anderson Silva, Ronda Rousey vs Cris Cyborg and many more. They all had the same stories: fighters in different places, the offer being too low, and by the time things could come together, fighters had already suffered losses and the interest had long dissipated.

This is why matchmaking is more a matter of time than place. Once the hype is gone, there isn’t much one can do but pine over the fight that couldn’t be. However, fortunately for him, Dana White lives by the ‘no regrets’ mantra. But for fans, it’s not the same.