‘Gangster-type characters’–Joe Rogan reveals one of his biggest regrets as he opens up on Dana White’s chilling encounter with ‘gangsters’

Joe Rogan admits one of his biggest ever regrets is Dana White’s failed negotiations with ‘gangster-type characters’ stopping a potential MMA super-fight from happening.

Rogan, who has spent over two decades as lead commentator in the UFC, opened up on the disappointment he still feels today over the breakdown of the contest, which came after White’s terrifying encounter on the island nation of Curacao with a ‘dangerous’ Russian entourage.

The proposed fight in question was between Russian heavyweight Fedor Emelianenko and American rival Cain Velasquez, who was recently sentenced to five years in prison over attempted murder and gun assault charges.

Emelianenko and Velasquez are considered two of the best heavyweights the sport has ever seen, with both men winning world championships in ex-Japanese promotion PRIDE and the UFC respectively.

And while they competed in different organizations, Rogan has revealed MMA fans were almost treated to a mouthwatering showdown between the now-retired pair.

‘My main regret in MMA is we never got to see Fedor fight in the UFC when he was in his prime,’ he told UFC fighter Ilia Topuria on the latest episode of his Joe Rogan Experience podcast.

Long-time UFC commentator Joe Rogan has revealed his biggest regret ever in the MMA world

Rogan says Fedor Emelianenko (left) vs Cain Velasquez (right) not happening pains him most

He explained how Dana White (left) had failed talks with Fedor’s ‘gangster-type’ entourage

‘If I could have one thing, one fight in their prime, Fedor vs. Cain Velasquez. In their prime. That would have been incredible.’

Rogan went on to explain how White was in talks with Emelianenko about bringing him over to the UFC to face Velasquez, before the Russian’s intimidating managers proved too ‘dangerous’ to do business with.

Reports at the time claimed the UFC President even jetted to Curucao – a Dutch-Caribbean island 40 miles north of Venezuela – to thrash terms out with Fedor’s team. To this day, both parties blame each other for the eventual collapse of negotations.

‘I’ve got to be careful how I say this: Fedor was controlled by some Russian people that were very rough men, as it were. Gangster-type characters,’ Rogan continued. ‘They had a bunch of negotiations with the UFC, but they were very unreasonable demands.

‘They wanted part of the promotion; they wanted to own a piece of everything because they knew with Fedor, they had their golden ticket, and they wanted to play it out as much as possible.

‘Negotiations were very intense and very confrontational. They got bad, where Dana had to up his security. It got pretty heavy. These were dangerous people… It got crazy.

‘In his prime, Cain Velasquez vs. Fedor. That’s my biggest regret. A fight that we never got to see.’

Emelianenko, 48, reigned as PRIDE Heavyweight Champion from 2003 up until the organization was dissolved in 2007. He is widely considered the greatest fighter to never compete in the UFC.

As for Velasquez, the 42-year-old captured the UFC’s heavyweight crown on two occasions, before hanging up his gloves after a knockout defeat to Francis Ngannou in 2019.

Last month he was sentenced to five years in prison and four years of supervised probation after allegedly engaging in a car chase and shooting at a man who was accused of molesting his four-year-old son in 2022.