Eddie Hearn didn’t expect Conor Benn to be the name that would walk away, and that’s the part that’s clearly left him devastated. After nearly a decade of building Benn inside Matchroom ever since his pro debut in 2016, the sudden switch to Dana White’s Zuffa Boxing landed like a gut punch for the British promoter. This wasn’t a slow drift or a contract standoff played out in public. It was realizing the trust he leaned on didn’t protect him in a sport where timing and leverage move faster than loyalty.

“I just felt that the loyalty that we’ve shown would never ever put us in this position,” Hearn lamented to IFL TV’s Kugan Cassius. “And I just felt that I never really needed to push Conor Benn to sign a new contract previously. I blame myself. I made a mistake because I misjudged the character. When I received the email from his lawyer, I texted him and said, I think we should have a call. And he said, nah. And I was like, man.

“Joshua, you can’t mention those two in the same name for many, many reasons. Joshua is a different breed of class and loyalty. Yeah, Joshua is one of a kind. Joshua is someone that even if I made the mistake of trusting that loyalty, it would never be a mistake with him because he’s cut from a different cloth, but there we go, that’s life.”

The point wasn’t just praise for Joshua. It was a line in the sand about how Eddie Hearn reads character in business. AJ has headlined stadiums, sold millions of tickets, pay-per-views, and still stayed put with him through wins and losses. Benn, despite beating Chris Eubank Jr. in their rematch and becoming mandatory for the WBC welterweight title, chose the disruptive promise of Zuffa instead.

From a business angle, you can see why Zuffa wanted Benn. He’s 29, carries a famous name, and just proved he can headline big nights. Dana White has been open about wanting to disrupt boxing’s old power structure, and signing Benn right as the rivalry with Hearn heats up is a clean PR win.

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For Eddie Hearn, the wound is personal, but the lesson is professional. He admitted he should have locked Benn down earlier. That’s rare candor in promoter talk. It also frames the Anthony Joshua comparison as more than sour grapes. Hearn is saying loyalty still exists in boxing, but it isn’t automatic. You have to protect your position even when the relationship feels solid. But while the Matchroom boss is reeling from the shocking exit of Conor Benn, Dana White couldn’t be more excited!

Dana White showers praise on “beast” Conor Benn after snatching him away from Eddie Hearn

Dana White didn’t tiptoe around the signing. He leaned into it as proof that Zuffa Boxing is serious about raiding boxing’s top shelf.

“Conor Benn is an absolute beast and a superstar,” said the UFC boss after securing Benn’s contract. “He shows up every time and destroys people, and now some of the best fighters in the world are calling him out.”

The sales pitch is clear: Benn isn’t a prospect project. He’s being framed as a ready-made headliner in a new ecosystem. The timing helps the hype. Benn has won 24 of his 25 pro bouts, with his only loss coming in the family rivalry against Chris Eubank Jr. The November win in their rematch put him back in title conversations.

In the traditional lane, he’s on the brink of a world-title shot. In Zuffa’s lane, the promise is bigger stages and a faster path to being the face of a belt White wants to elevate above the WBO, WBC, IBF, and WBA, alongside The Ring title backed by Turki Alalshikh.

Yet, Conor Benn isn’t pretending the split has to be permanent. He said he hopes Hearn can still be involved down the line. But his ambition is clear: “legacy fights, the biggest nights, the biggest stages.”

For Benn, the move is a bet on scale over stability. Zuffa is offering him headline status in a project that wants to redraw the map of boxing titles. If it hits, he’s early and powerful. If it stalls, he’s stepped off a clear world-title road for a vision still being built. That’s the trade-off he’s chosen. And for Eddie Hearn, the Anthony Joshua comparison lingers as a warning to himself as much as anyone else. Loyalty exists in boxing. It’s just not a contract.