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The most difficult battle for many fighters isn’t in the ring, but knowing when to leave.

Boxers who couldn’t resist one more fight, one more shot, or one last last doubtless have a history of success.

James DeGale, an Olympic gold medalist and former IBF super-middleweight champion, is no exception.

The 39-year-old will practice bare-knuckle boxing on Saturday in Manchester, one of the most brutal competition sports.

Six years after the humiliating defeat of Chris Eubank Jr., which ended his career, he encounters Australian Matt Floyd at the AO Arena, a memory that still nags at him.

He claims that Eubank plays in his head every day because of how he played it. “I want to leave with a positive outcome and demonstrate my injuries to others.”

DeGale is aware that his choice will raise eyebrows, but he thinks that gaining public support and retribution might lead to a return to traditional boxing.

He tells BBC Sport, “The last few years of my career I was plagued by injuries.”

“Just to show how handicapped I was, I need to correct the mistake and conduct a few more fights.”

DeGale believes the contemporary boxing landscape, which has been shaped by crossover competitions and influencer fights, offers fresh opportunities.

He claims that his work has been accomplished by winning world titles and boxing at the very top.

“Boxing has, however, changed. Misfits, shows in Qatar, and money are everywhere, according to [YouTuber KSI’s promotional company].

However, accidents and subpar performances caused pain. A messy rematch victory saved Caleb Truax’s defeat in 2017, while Eubank’s 2019 defeat felt final.

DeGale claims that he realized he was neurodivergent toward the end of his career.

Neurodivergent, a term used to describe the range of brain function differences, including ADHD, autism, dyslexia, and synesthesia, accounts for one in five people.

I was given a severe ADHD diagnosis at the end of my career. “Proper ADHD,” DeGale claims.

It had a significant impact on me. I was concerned about what people would say and think.

At the time, I was “probably a little mentally sluggish.”

Individuals with ADHD experience a variety of difficulties, including reluctance, impulsivity, and poor concentration control.

DeGale believes that his poor judgment was caused by ADHD, but he now feels grounded thanks to medication and experience.

He claims that he didn’t want to repair and heal the ring after the year and a half.

DeGale has no desire to fight into his 50s and left boxing with his health intact.

Yet a comeback persisted, and bare-knuckle offered a solution.

People said, “James, leave it, you smashed it,” because I had such a successful career. He claims that there weren’t many opportunities before this one emerged.

“This is a method for getting attention,” Rejoin the most brutal sport in the world and deliver a performance.

Floyd, a Perth fighter with a 15-2 professional record and a history as a former gang member who spent time in prison, is his immediate target.

The event features a Bare Knuckle Fighting Championship card.

DeGale describes boxing as “boxing but without gloves.”

“When you’re in a clinch, you can punch someone with the back of their neck,” they say.

Adapting well-known routines has become a necessity as a result. He has relied on knowledgeable experts to help him because it would be too harmful to spare his bare-knuckle.

“I’m getting bare-knuckle fighters, and they’re giving me all kinds of advice. The Londoner claims that she has been strengthening her forearm and hand.

“You don’t realize how shaky your hands are until you start slamming the bag with your bare hands.”

DeGale is aware that a man who has already accomplished so much is taking a chance on this comeback.

However, this “organised straightener,” as he puts it, might allow a fighter to leave on his own terms for a fighter whose career ended in regret.

For many fighters, the hardest battle is not in the ring but knowing when to walk away.

History is littered with boxers who could not resist one more shot, one more fight, one last chance to silence the doubts.

Olympic gold medallist and former two-time IBF super-middleweight champion James DeGale is no different.

On Saturday in Manchester, the 39-year-old will step into one of the most brutal arenas in combat sports: bare-knuckle boxing.

He meets Australian Matt Floyd at the AO Arena, six years on from the punishing loss to Chris Eubank Jr that ended his career – a memory that still gnaws at him.

“The way I went out against Eubank, it plays in my head every day,” he says. “I want to go out with a good win and show people how injured I was.”

DeGale knows his decision will raise eyebrows but believes attention and redemption could pave the way back to traditional boxing.

“The last couple of years of my career I was riddled with injuries,” he tells BBC Sport.

“I need to right the wrong and have a couple more fights just to show how handicapped I was.”

Although world titles are behind him, DeGale feels the modern boxing landscape – shaped by crossover shows and influencer bouts – offers new opportunities.

“Boxing at the very top and winning world titles again, that’s done,” he says.

“But boxing has changed. There’s [YouTuber KSI’s promotional company] Misfits, shows in Qatar, money everywhere.

DeGale made history as Britain’s first boxer to win both Olympic gold and a professional world title, capturing the IBF super-middleweight crown in 2015 and defending it against top names.

But injuries and underwhelming performances took their toll. Defeat by Caleb Truax in 2017 was salvaged by a messy rematch win, while the Eubank loss in 2019 felt final.

DeGale says towards the end of his career he discovered he was neurodivergent.

One in five people are neurodivergent, an umbrella term for the range of differences in how our brains function, which includes ADHD, autism, dyslexia and synesthesia among others.

“At the end of my career, I got diagnosed with severe ADHD. Proper ADHD,” DeGale says.

“It impacted me a lot. I used to worry about what people would think, what they would say.

“I was probably a bit mentally weak at that time.”

ADHD challenges vary from person to person, but they can include hyperactivity, impulsivity and difficulty regulating focus.

DeGale believes ADHD contributed to poor decisions he made, but with medication and experience, he now feels grounded.

“I didn’t want to take that year and a half out of the ring to repair and heal,” he says.

DeGale left boxing with his health intact and has no desire to fight into his 50s.

Yet a comeback still called to him and bare-knuckle offered a route.

“I had such a good career, people said, ‘James, leave it, you smashed it’. There weren’t many opportunities, but then this came up,” he says.

“This is a way to get attention. Come back in the most brutal sport in the world and put on a performance.”

His immediate task is Floyd, a Perth fighter with a 15-2 professional record and a past as a former gang member who served time in prison.

The fight headlines a card for Bare Knuckle Fighting Championship.

“It’s boxing but with no gloves,” DeGale explains.

“There are some different rules: when you’re in a clinch you can hold the back of their neck and punch.”

Preparation has meant adapting familiar routines. Sparring bare-knuckle would be too damaging, so he has leaned on experienced specialists to guide him.

“I’m training with bare-knuckle fighters giving me all kinds of tips. I’ve been strengthening my hand and forearm,” the Londoner says.

“You don’t realise how weak your hands are until you start punching the bag and pads bare-knuckle.”

DeGale knows this comeback is a gamble for a man who has already achieved so much.

But for a fighter whose career ended with regret, this “organised straightener”, as he puts it, might allow him to walk away on his own terms.