Few players have fallen further from favour with Arsenal fans than David Bentley, the once-promising academy graduate turned Tottenham cult figure, who now finds himself preparing for a boxing match against former Chelsea midfielder Jody Morris.
Bentley, 41, who was once compared to Dennis Bergkamp and touted as “the next David Beckham” while rising through the ranks at Arsenal, will enter the ring tonight at London’s Grosvenor House Hotel as part of a charity event organised by former Arsenal goalkeeper Graham Stack.
The event features five bouts between ex-professionals and aims to raise £500,000 for Playskill, Sport in Mind, the Willow Foundation and Helping Hands.
“I like to create chaos but I don’t like to be surrounded by it,” Bentley said ahead of the event. “I’ve got four children that I’m raising, they probably think I can’t fight. So it’s to showcase to them: ‘Look, you can do anything if you put your mind to it and you can step into the most uncomfortable situation.’
“You have to have courage to even step into that ring, get your head whacked and take it.”
Bentley’s opponent, Morris, spent much of his career at Chelsea before moving into coaching and says about Bentley. “I didn’t know him from Adam,” he said. “He was a very good, technically gifted footballer. Yeah, I’m hoping his technical ability in the ring is not the same.”
The pair have no personal history, though Bentley has long been known for confrontational style. During his Arsenal days, he once refused to give up Patrick Vieira’s canteen seat and admitted to nearly fighting Thierry Henry in training. “Sure, Thierry is one of the best players to ever live, but he was mugging me off that day, trying to dictate the session. I had a goal disallowed.
“He was trying to make up his own rules and it went off. I had gloves on, so I’ve whipped my gloves off. ‘Come on, then!’ It never came to blows, thank God, because Henry would have laid me out.”
Morris, who has been trained by former world champion Darren Barker, revealed that his own preparation has been far from easy. “I got a decent hiding in sparring,” he said. “I was just at a gym in Aldgate East and they got a Ukrainian kid in, a southpaw. I’m pleased to be out the other side of it, and not go down. This kid was punching miles harder than what Bentley is going to do.”
Bentley’s decision to return to the public eye in such a spectacle has surprised many. Since retiring aged just 29, he has built a life away from football, running businesses in Marbella and occasionally working in broadcasting. Once seen as one of Arsenal’s most gifted prospects, his move to Tottenham in 2008 and his goal celebrations against his former club made him one of the most disliked ex-Gunners in recent memory.
Stack’s “Box2Box” event has attracted significant attention, with other bouts involving Paddy Kenny, Curtis Davies, Lee Trundle, and Anthony Gardner, as well as ringside appearances from James DeGale, George Groves, Peter Crouch, Paul Merson, and Ray Parlour.
Bentley made nine appearances for Arsenal, scoring once, before being sold to Blackburn for just €1.75m in 2006.
Two years later, Tottenham paid €22m for him. Over the course of the next five years, Bentley made 62 appearances for Tottenham but also spent time on loan with Birmingham, West Ham, Rostov and Blackburn before being released in 2013.
After a year without a club, Bentley announced his retirement from playing in 2014.