The 31-year-old first signed with Frank Warren and Queensberry in February 2019 when he was an 8-0 prospect.

In the seven years since, Bentley (22-3-1, 18 KOs) has made 18 appearances. He's won the British title three times, held European honors once, and is currently the WBO middleweight champion.

However, lacking a physical contract with the promotional company left Bentley feeling vulnerable. With a young son back home, Bentley's need for security was clear before approaching what he describes as “the latter stages” of a career that started nine years ago this month.

In stepped Zuffa Boxing, Dana White’s upstart promotional venture, which was more than happy adding Bentley to their already bustling middleweight roster.

“It was definitely hard to walk away after such a long association,” Bentley tells The Ring.

“It has been a long journey with them and you’re also thinking it might be a case of better the devil you know. 

“I know Frank and going to the Queensberry office, he's always been nice and kind to me, but ultimately I just had to make a decision for myself. I just had to figure out what was the best decision for me and my family. Essentially, it was just getting a bit quiet.”

Bentley last fought on April 4, when beating Endry Saavedra to claim the vacant WBO interim title. He would eventually be upgraded to full champion in July after Janibek Alimkhanuly relinquished his belt. That clash with Saavedra was his first outing in 16 months and only his fourth since his 2023 defeat to Nathan Heaney.

That 16-month period had become a particular bone of contention for Bentley, the reigning European champion at the time.

Given he was high in the WBO rankings, he was due a world title shot and Warren did not want to jeopardize any world title opportunity by arranging a fight in the interim. Bentley could have sustained injury, suffered defeat or simply been overlooked by the WBO had he been scheduled to fight someone else when they called.

But Bentley, who was in the gym everyday regardless, would have been more than happy to defend his European title and maintain sharpness for whenever the world title fight order came.

In the end, he did become world middleweight champion this year, but his boxing earnings had dried up so considerably that he nearly became an Amazon delivery driver to keep his family afloat.

“Sitting out those 16 months really made me think that if they don't need me, they're not going to use me,” he says.

“Obviously, we hadn't had a contract for a while, and everything was based on handshakes and the relationship between him and my manager.

“I can't say me and Frank had much of a relationship but every time I saw him, he greeted me and made sure that I was all good. I’ve got nothing bad to say about him per se.

“They helped me get my career onto this track that it's on now but at the end of the day, when it came to Queensberry as a whole, I just felt like I wasn't directly in their plans.

“The long lay-off just put a lot of things into perspective for me. I'm here but don't have a contract so they're not really obliged to do anything.

“I'm just in no man's land because I'm not in a position to complain or throw my toys out of the pram; I'm a free agent anyway and can make any decision I want.

“I couldn't just keep living my life like that or having my career in that situation, not knowing what I'm doing with myself. So I just had to make a decision. The whole thing was mentally frying my brain so I’m happy it’s done.”

A few weeks after his victory over Saavedra, the Londoner was made aware of interest from Zuffa Boxing, who at the time were preparing for their first-ever UK show on June 6.

As one of Britain’s most entertaining fighters, Bentley emerged as a key target. That's especially considering the Zuffa roster already boasts IBF middleweight champion Aaron McKenna and Conor Benn, who is expected to operate around 160 pounds upon his return.

“When I spoke to them, the first thing they said to me was, ‘look, you sitting out for 16 months will never happen with us.’

“They said that’s far too long on the shelf. They have all their fights and dates lined up for the year already because they need to know their schedule.

“Obviously Dana White wants to be at every show and has a busy schedule so they need to know when and where they can fit everyone in.

“So they’ve got all these shows and, although they have been making signings, it’s not like they have hundreds of boxers. It means they would have to use all the fighters they have already signed.

“So there was just more stability in the sense that I will be active and, as soon as they announced me signing on Friday, I got a date on November 7. So we're off to a good start, I guess.”

It has been confirmed that Bentley will make his Zuffa Boxing debut against Shane Mosley Jr. at London’s Copper Box Arena as part of the card headlined by Billam-Smith’s clash with amateur rival Chev Clarke.

The show will be broadcast on Sky Sports in the UK and Paramount+ in the US.

Bentley has been ordered to defend his WBO title against mandatory challenger Yoenli Hernandez but has appealed to the sanctioniong body, allowing him to face Mosley Jr. as champion first.

At the time of writing, he has had no response and remains champion.

“Ideally I would like to keep my WBO title because I worked hard for it,” he added. “It's not something I'm just trying to throw away. It’s not like I don't want this no more because I want the money. That's not the situation.

“The appeal is going through and hopefully we end up on the right side of it.”