Ranking 5 biggest flops in Tottenham Hotspur history
The wait for a major trophy continues at Tottenham Hotspur, who last lifted a piece of silverware in 2008 when they won the League Cup. Since then, managers have come and gone but their attempts to help the club win a trophy have been in complete vain.
This is not to dismiss the hard work they have done, but ultimately, they haven't had anything to show for. They came very close to losing their superstar Harry Kane, arguably the most important player at the club in their recent past, last summer. Manchester City were quite close to sealing a deal for him.
Tottenham Hotspur have had their share of disappointment in big signings
The north London club's dry spell has really tested the England international's patience and he could soon be on his way out if no signs of progress emerge. Speaking of star players, one of the reasons for the north London club's long wait for titles has been the number of flops they have signed at the club.
Many players who had shown great promise were signed by the club to help them move closer towards their ambition. But eventually, they failed to honor the badge and produce what was expected of them. Here is a look at five of the biggest flops in Tottenham Hotspur history.
#5 Helder Postiga
When a technically gifted player like Glenn Hoddle suggests that fans are going to enjoy and be entertained by a player, he must really rate that player highly. Hoddle was the manager of Tottenham Hotspur from 2001 to 2003, a club he also represented in his time as a player.
The former England international was impressed by Helder Postiga who, with his burgeoning reputation, garnered many suitors in Europe. The Lilywhites paid £9 million, a fairly significant amount in 2001 and signed the Portuguese from FC Porto.
But his stock really took a bad hit during that spell and he was no longer the exciting prospect from Portugal. Postiga could only manage two goals in 23 appearances for Tottenham Hotspur, although both those goals contributed to a winning cause.
10 years since Helder Postiga did THIS 🤩🚀
https://t.co/f0HP4k0eFR
Fans were left scratching their heads, having no idea how they managed to sign such a dud. Perhaps it's reasonable to say that they stopped judging players based on Hoddle's assessment afterwards.
#4 David Bentley
Arsenal fans must sometimes feel like they dodged a bullet letting go of David Bentley at the right time. The wide midfielder was earmarked as one to watch out for in the future but there were doubts whether he was completely devoted towards making it to the top level.
He made nine appearances for Arsenal, of which only one came in the Premier League and scored his only goal for the Gunners in an FA Cup tie. He was sold to Blackburn Rovers in 2006 where he found his feet and proved to be a real bargain at just €1.75 million. Bentley wasn't as much of a scorer as he was a provider.
On the right flank, he had the knack of finding players in the box and hurling effective crosses. This led to him registering an impressive assists tally of 10 and 11 respectively in two PL seasons along with four and six goals in the 2006-07 and 2007-08 seasons respectively.
♂️ An 80-yard dash
A month in Superman pants🚀 A 39-yard screamer
🏃♂️ An 80-yard dash
😅 A month in Superman pants
The #NorthLondonDerby in 2008 was one to remember for David Bentley! https://t.co/4q9LOk6tyt
This prompted Tottenham Hotspur to fork out £19.80 million in 2008 and sign the former Arsenal academy graduate. He was being compared to David Beckham, not only because of the initials but because his first touch was sharp. His ball control was also impressive and he could deliver some seriously good passes.
But in his five years at the north London club, his moments of brilliance were rare and he was no longer creating decisive chances for the forwards to finish. His overall impact and ability to influence the game was fading. Tottenham Hotspur soon ran out of patience with him after he was involved in a drink and drive accident.
Bentley went on multiple loan spells at several English clubs and also to relegation battling Russian club Rostov. He finally retired from football in 2013, aged just 29 and confessed that he had fallen out of love with the sport.