Of the many ‘what if’ fights in UFC history, none might be bigger than Fedor Emelianenko vs Cain Velasquez. The heavyweight juggernauts dominated like few others, but never shared a stage. Well, as it turns out, there’s more than just negotiation tactics and contracts to blame for this one not happening.

Sitting down with Terence Crawford, Joe Rogan got into what he still sees as the biggest “what if” in MMA history: Fedor Emelianenko vs. Cain Velasquez. And this wasn’t just a fantasy matchup between eras or a social media pipe dream. It was a real fight, at a real time, that almost happened. According to the JRE host, things just got too messy.

“Fedor was the big dog,” Joe Rogan told the former undisputed super middleweight champion. “At one point in time, he was f—— everybody up. Slamming them, arm-barring them, f—— people up standing.

“He was complete. And he was, at the same time, where Cain Velasquez was in his prime, and that was the fight that they tried to put together.”

Cain Velasquez was terrifying at his peak. He dominated his division with unrelenting pace, never-ending cardio, and mauling pressure. Meanwhile, ‘The Last Emperor’ was the monster his peers dreaded.

Rogan believes that the overlap was a sign of magic waiting to happen. But negotiations weren’t simple. Why? Well, according to the JRE host, once Pride’s contracts unraveled, the Dana White-led promotion had to negotiate with some really dangerous men.

“Because the UFC didn’t have a contract with Fedor anymore, because the contracts at Pride were all bulls—,” Joe Rogan explained. “They had to deal, you know, with these Russian gangsters. And these Russian gangsters were like, you know, they wanted a piece of the promotion. They wanted a lot.

“And the UFC wasn’t willing. It got very contentious, so the UFC had to up their security. It got sketchy. Those are bad dudes. But it’s just, as a fan, we were robbed. We were robbed of, like, one of the greatest matchups in the history of the sport.”

In the end, the deal never materialized. Fedor Emelianenko went on to fight elsewhere. Cain Velasquez built his legacy within the UFC cage. And the dream fight became all but a pipe dream. And that’s the part Joe Rogan can’t get over.

However, it is worth noting that while the JRE host is telling the UFC’s side of the story, if you ask ‘The Last Emperor’ about the same, his version sounds a lot different. In fact, he simply blames the UFC head honcho for the fight falling apart.

Emelianenko’s version of events about his only meeting with Dana White

Joe Rogan’s account describes heated negotiations and dangerous middlemen. But if you listen to Fedor Emelianenko, the story becomes a lot less dramatic—and far more personal. From his perspective, it was not about gangsters or chaos. It was about timing, contracts, and a meeting that never felt right.

According to ‘The Last Emperor,’ when he eventually sat down with the UFC CEO to book the fight, he was already under contract with Strikeforce. As a result, signing with the Dana White-led promotion at that period would have gotten him into serious legal trouble.

“I fought many UFC champions [in my career], and I was beating them all,” he said in a 2023 interview. “So it doesn’t really bother me that I didn’t fight there. There was a moment when the UFC purchased Pride that it was a possibility. But Dana White didn’t sign the contract.

“I had a current contract with Strikeforce while Dana White was offering me a new contract with the UFC. If I signed that contract, I would’ve been stuck. I would’ve had to go to court, and I wouldn’t have been able to fight for UFC or Strikeforce.”

The sole face-to-face meeting he recalls did not have a lasting effect. Fedor Emelianenko claims Dana White approached him while he was on vacation. To him, the offer, the setting, the energy—none of it felt solid, a completely different story from what Joe Rogan claimed. But what’s true is that just like that, one of MMA’s most promising crossovers dissolved into history, depending on whose side of the fable you believe.