If Eddie Hearn was upset, it is fair to wonder what his father, Matchroom’s founder and president Barry Hearn, must be feeling. Conor Benn made the jump, leaving Matchroom Boxing for Dana White’s Zuffa Boxing in a $15 million deal – a ten-year relationship undone in a matter of moments. As much as the split left many shocked and bewildered, for the Hearns, who have been with Nigel Benn’s son since the day he made his professional debut and through some of his toughest battles outside the ring, it amounted to a cheap shot.

“I mean, it’s classless; it’s a classless way of doing it when you’ve got an open relationship,” said Barry Hearn in a recent interview with talkSPORT. “We took a lot of heat over this. You know, we took a lot of stick for our company reputation and personal reputation when we stood by a guy that failed a drug test twice and said, ‘No, we believe in him’.”

Hearn Sr. was referring to the scandal that erupted in the latter half of 2022. In the days leading up to his scheduled fight against Chris Eubank Jr., reports emerged that Benn had tested positive for the banned substance clomiphene.

While he voluntarily relinquished his British Boxing Board of Control (BBBofC) license, he also faced suspension from the United Kingdom Anti-Doping Agency (UKAD), placing his career under immediate scrutiny.

Throughout the ordeal, Eddie Hearn and Matchroom Boxing stood by him, allowing him to compete in US-based events and keep his career moving. Reports indicate that Hearn helped Benn with £500,000, roughly $600,000, during the crisis, further underlining the level of backing he received.

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“It is very disappointing considering everything I have done for him. Maybe I misjudged his character,” Eddie Hearn said. “I just think the way it was done was very, very wrong.”

In the opposite corner: Conor Benn answers the Hearns

Part of Eddie Hearn’s frustration centered on how the negotiations unfolded. During the interview, he claimed that communication went through lawyers only. He did not receive direct access to Benn during the negotiations.

“Conor was as close as he could have been to being part of the family,” his father highlighted, adding, “And for him to make a decision like this without even a phone call, or actually, when Eddie suggested to him by text that they meet to discuss it, Conor suggested it was best to go through lawyers, and after 10 years of what we’ve gone through with him, I think in my 50-odd years of promoting sport, this is the most horrible, outrageous…”

In response, Benn explained his side of the story, saying he did not deliberately avoid speaking to Eddie Hearn. Pushing back on the idea that he refused contact, he said tensions between the two camps were running high during negotiations, and he questioned whether a direct call at that moment would have been productive.

Benn maintained that, given how tense and emotional the moment was and how quickly things could have spiraled, hurt, pride, and anger might have led to regrettable remarks. His silence, he suggested, was a measured decision rather than a sign of disloyalty. Benn called it a mutual misstep, not a one-sided breakdown, and admitted he could have handled it better.

The back-and-forth between Benn and the Hearns may continue for some time. The welterweight fighter has already hinted that he would like his association with Matchroom Boxing to continue. Yet the episode underscores the fragile nature of loyalty in a sport where, increasingly, money has become the ultimate deciding factor.