The summer of 2008 seems a long time ago now. It was before Manchester City had been taken over by Sheikh Mansour, Cristiano Ronaldo was toasting his second successive Footballer of the Year award, and Tottenham's manager was Juande Ramos.
Damien Comolli was in charge of the club's transfer affairs, the man who would later sanction a £35 million bid for Andy Carroll, and £40 million on Jordan Henderson and Stewart Downing while at Liverpool.
So looking back, it is hardly any wonder that he oversaw Tottenham spend £15 million on signing David Bentley from Blackburn Rovers.
To be fair to him, Bentley had been terrific for Rovers in the two seasons he was there, contributing an impressive 15 goals and 26 assists across 2006-07 and 2007-08.
Three of those goals came in a sparkling 4-3 win at Ewood Park over Manchester United, a memorable hat-trick in a match which saw Rio Ferdinand sent off for hacking down Robbie Savage.
He was even linked to United at one stage, and became desperate to move to a 'bigger club' to feed his England ambitions, which weren't helped when Steve McLaren dubbed him 'The next David Beckham'.
So Tottenham took the plunge and parted with £15 million for Bentley's signature. It seemed inflated but perhaps not unreasonable at the time considering his performances and potential.
Now it seems like one of the best pieces of transfer business in the past decade. Except for Blackburn not Tottenham.
After going eight games without a league win at the start of 2008-09, Juande Ramos was dismissed and Harry Redknapp appointed. Bentley scored a memorable long-range goal against former club Arsenal in the new manager's first North London derby, but it went downhill from there and almost four years on that remains the highlight of his Spurs career.
As a right-sided midfielder, dislodging Spurs winger Aaron Lennon was always going to be a difficult task, and he soon found himself benched, and that was how it stayed. With Gareth Bale's emergence, Harry Redknapp's preference was always going to be the twin threats of Bale and Lennon on the wing, and Bentley appeared to quickly get disheartened.
His presence as a fringe member of the squad was confirmed with loan spells at Birmingham and West Ham, both forgettable experiences with the player failing to make an impression at either club, and his spell at the Hammers ruined by injury.
He talked of being given a clean slate under Andre Villas-Boas, but if he was then the manager also decided he wasn't worth persisting with. Fair play to the midfielder for pushing for a move even when the deadline in England had passed, and he has got his reward thanks to Russian club Rostov.
Bentley may resurrect his career, and most football fans will hope he can, he had the potential to be a wonderful talent and to see his potential fall by the wayside has been disappointing to watch.
The way it has done, makes the £15 million deal seem astounding, for he has not repaid Spurs even a third of that, and with the benefit of hindsight, Blackburn definitely pulled off one of the great sales of recent times.
Watch Bentley's hat-trick for Rovers against Manchester United...
Why do you think it went so badly wrong at Spurs for David Bentley?
image: © wonker
Dan Coombs
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Dan Coombs is a writer who is keen to embrace the internet revolution. He first started writing for us in June 2011 and commenced his new role as Sports Editor in February 2012.
As a trained journalist he has met famous faces from Mr T to Boris Johnson. He once featured in an England World Cup music video too, but it did not make the charts.
He grew up wanting to be a Formula 1 driver, but it looks like this dream has passed him by. Instead, he hopes you enjoy reading his writing on our site, as we seek to debate the day's sporting hot topics.
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