After bursting on to the scene as an Arsenal academy graduate, following loan spells with Norwich and Blackburn Rovers, he joined the latter on a permanent deal.
Between 2006 and 2008, Bentley saw the best years of his career as a winger, even breaking into the England international set-up.
But a big-money move to Tottenham wouldn’t work out. Bentley played 42 times for Harry Redknapp’s side, scoring only twice (once, admittedly, was one of the best ever scored in a north-London derby).
After falling out of favour at White Hart Lane, he was loaned out to Birmingham City in 2011, then West Ham, before he spent time in Russia with FC Rostov before a return to Blackburn.
But Bentley stunned the football world in 2014 when he announced his retirement at just 29 years old.
He moved his family to the foothills above Marbella in Spain, and recently admitted he was worn down by the pressure and fame of elite football.
Now 32, he told the Daily Mail earlier this year: ‘I didn’t want to go in the David Beckham direction. We had meetings with people who operated for these superstar players but I couldn’t see the point. What for, more money?’
He also mentioned that he never really considered himself as a winger, a position where he was deployed for most of his career.
He did play No 10 off Shefki Kuqi when he scored a hat-trick against Manchester United in a 4-3 win at Ewood Park for Blackburn in 2006.
With his vision, technique, and exceptional ball-striking ability, it’s difficult not to wonder whether Bentley could have been a world beater had things been a bit different.