They said he could be the next Paul Gascoigne and, when he moved to midfield, the next David Beckham. His crossing was superb, his corners deadly and, on form he seemed unstoppable.
So why has David Bentley, the England star who cost Tottenham Hotspur £15 million, given up football at only 29 and gone into the restaurant business? It was a heartbreaking decision – Bentley cried when he broke the news when being interviewed on TV — but it was a simple one. "I've fallen out of love with the game," he says. "Football has become boring. I want to take my life in a different direction.
"I've got baby twins of three months old and a four-year-old son and I want to focus on that. I wouldn't want to carry on playing football just for the money. I'm involved in a Spanish restaurant chain which we're bringing to the UK and so there's a lot of work there."
But friends say there's more to it than that. The self-confessed bad boy of football just couldn't cope with the restrictions of a game which had become big business. "I fell out with pretty much every manager I played for," admits the man who poured water on Harry Rednapp and called England boss Fabio Capello 'Postman Pat'.
Says his friend and former England colleague Jimmy Bullard: "Bents was a great lad – the bloke is an absolute wrong-un but a lot of fun and a great character! But he just couldn't toe the line when it came to discipline and doing what he was told."
Of course David Bentley has regrets about retiring probably five years earlier than he needed to. "Football was a sport I loved to play," he says now. "I did it for enjoyment. You express yourself but you find that when you reach the top level it becomes a job."
David admired players who didn't conform – stars like Paul Gascoigne, Paul Scholes and Eric Cantona. "They were performers and their presence was unbelievable. Nowadays you don't see character and charisma. Every team plays the same; every player does the same thing. They're a brand and they just do their job. I could never play like that." From the beginning everyone expected great things of David Bentley. He had been spotted by a scout playing in a school match and joined Arsenal at 13, meeting and learning from legends like Patricck Viera, Dennis Bergkamp, Thierry Henry and Robert Pires.
Arsene Wenger, never one to be generous with lavish praise, thought the youngster could become the best player of his generation and the then England manager Steve McClaren labelled him the new David Beckham after seeing him land 60-yard crosses unerringly on target. But with so many superstars at Arsenal, the youngster felt he was spending too much time on the bench. He wanted to play and persuaded Arsene Wenger to send him out on loan, first to Norwich and then to Blackburn Rovers.
"I loved it there," he says. "They were my sort of team." He was their sort of player, too – he moved permanently to Blackburn on the final day of the 2006 transfer window and celebrated with a Premier League hat-trick against Manchester United the next day.
When England called, David played seven times for his country after captaining the Under 18s and playing in the senior B team. Now he criticises the England team philosophy as being too strict and stifling any individuality.
"We'll never produce top players until we change the mindset of the English game," he says.
Happily settled in Blackburn, David Bentley became the new Premiership sensation, pursued by United, Liverpool, Arsenal and Chelsea, but he preferred to stay at Blackburn. "It was like a family," he recalls. "There were a lot of characters there, like Robbie Savage and David Flitcroft who only played to have a good time and that's what I was doing.
"It was an old fashioned club which looked after the supporters and money wasn't the most important thing. Everyone enjoyed being at Blackburn and I hoped to stay there for years. But sadly even at Blackburn money could talk and when Tottenham offered £15 million, rising to £17 million, for their 23-year-old star, they just couldn't afford to refuse. So David Bentley found himself at White Hart Lane on a salary of over £50,000 a week and within weeks all his worst fears were realised.
"Everything I didn't like about the big-time was there… being told what to say, what to wear, where to go, what to do and when to do it."
But he admits it was the water-pouring incident which probably wrecked his chances at Spurs.
"We had beaten Manchester City to get into the Champions' League in 2010 and of course everyone went mad.
"Some of the lads, including me, tipped a tub of water over our manager Harry Rednapp, but I was the only one who got it in the neck.
"Harry never forgave me. He must have lost his sense of humour that day. It was all good-humoured but he definitely didn't see it like that.
"It was a celebration of going into the Champions' League and nothing more, but I know I was always up against it after that and I hardly got another look-in. There was a total lack of communication from then on and I knew it was time to leave." After four loan spells, including becoming the first English player to play in the Russian Premier League for FC Rostov, David Bentley hung up his boots at the end of last season – and has never regretted it.
Now he and his family live in Spain, although they returned to the UK when the twins were born to give them British nationality. "People still stop me in the street and ask why I packed it in and will I ever change my mind?" he says.
"I say I might coach kids' teams but I'll never go back to professional football. For me there would be no fun in it anymore."