Where did it go wrong for him at Tottenham?

David Bentley, Tottenham Hotspur

Should David Bentley finally make his long-overdue departure from Tottenham Hotspur this month, the circumstances around his protracted exit are likely to be about as polarizing to his arrival at the club as you could possibly imagine.

Those interested in the former Blackburn Rovers winger shouldn’t be too concerned by his seven international caps, the array of technical gifts he gathered under Arsene Wenger or the £15million transfer fee it took for Spurs to once prise him away from Ewood Park.

In fact, should those wishing to take a roll of the dice with the former Arsenal apprentice fancy lining up a permanent deal this month, it should take little more than a nominal fee to pluck him out of Andre Villas-Boas’ squad. With his six-year-deal effectively ending a year early this summer and no place back for him within his manager’s plans, Spurs are set to take a huge financial hit on Bentley.

Yet where as he entered N17 as one of the great young hopes of English football, he’ll be leaving as one of its greatest ever wastes. And while an element of bad luck and a dashing of mismanagement have played their part in his tale, Bentley’s fate is ultimately one of sustained self-infliction.

At only 28-years-old, Bentley enters the prime-years of career seeking redemption, rather than seeking silverware. If he is to finally turn things around, the chances are he’s going to do it the hard way. With his last Premier League appearance coming in Birmingham City’s 2-0 defeat at home to Fulham in the May of 2011, it’s been over 18 months since he last played regular top-flight football. You have to go back even longer to find the last time he found anything resembling form.

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A move to the Championship seems like the most likely scenario, bar a desperate late enquiry from one of the Premier League’s contingent of struggling clubs. Although given the underwhelming nature of the last time a relegation threatened club took a chance with him, it seems unlikely that history might repeat itself. Indeed, the Birmingham Mail certainly didn’t sugar coat his time at St. Andrews, describing Bentley as ‘flattering to deceive’ in producing a raft of mistakes that proved ‘costly’.

Thing have of course gone from bad to worse for David Bentley and while no one can account for the knee ligament damage that deprived him of a desperately needed season of regular football for West Ham last term, the road to his current plight has been paved by his own failings.

When he does speak to the media these days, an increasing rarity as the years have gone by, the cocksure demeanor and the silhouette of arrogance seems to have eroded away.

In a recent interview following his loan move to FC Rostov, Bentley seemed more open, aware and acknowledging of the mistakes he’d made in the past:

“I thought I was James Dean in the day,” he said.

“If I saw a cliff, I’d want to jump off it.”

The James Dean comparison may have been given in good humour, but given his car accident in 2009 – ironically also in a Porsche – it certainly offers a painful insight into Bentley’s former mindset. His reputation as a troublemaker is perhaps verging on the unfair, but his decision to drive his 911 Turbo home after sinking four pints and two spirits with Aussie band Jet, delivered what Bentley described as a ‘wake up call’.

But regardless of his past alleged care-free attitude off the pitch, it was what he was doing on the field that was perhaps as disappointing as anything he was doing away from it.

Bentley’s often spoke about his disappointment in then-coach Juande Ramos’ departure and the lack of subsequent ‘communication’ with his successor Harry Redknapp. He’s even described his time under the now-QPR boss akin to ‘banging his head against a wall.’

Yet although Redknapp’s insistence on playing with two out-and-out wingers was always going to serve his fellow right-wing rival Aaron Lennon in a better way, Bentley offered little in the way of any fighting instinct. His lack of application for Spurs was never delivered with the sort of sneering attitude that generates widespread malaise from the stands; it was often more a half-hearted, neither here-nor-there sort of desire.

And for a man with such an unnerving amount of natural talent, Bentley’s approach at times in a Spurs shirt let himself down, as much as anybody else. For a self-proclaimed childhood supporter of the Lilywhites, it seemed strange that those who flocked to watch him at White Hart Lane were never treated to anything near the sort of performances those at Ewood Park were able to enjoy.

His time at Tottenham may well have inflicted irreparable damage to his reputation and he’ll never reach the level of which his ability once demanded. But for all the water that has since passed under the bridge, Bentley still has time to make one more positive mark upon English football.

Whether he still retains the hunger for the game after two bitterly disappointing years remains to be seen, but if a Championship side can give him the sort of environment needed to rebuild both his confidence as well as his career, then he has the talent to help any team in that division gain promotion.

Everyone deserves a second chance and David Bentley isn’t any different. And if he is lucky enough to be given that opportunity, then how he fancies being remembered in the game could define how he fares in his last chance saloon.

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