Five of Tottenham’s worst signings in the Premier League era

Spurs have had the likes of Diego Maradona and Rivaldo nearly join the club in the past, which is perhaps unfathomable to some. True to form, though, the club has also signed an array of flops who’ve failed to deliver during their time in north London. In fact, perhaps more than many other clubs, Tottenham’s recruitment has been notably poor on a number of occasions.  

Of course, Daniel Levy has also got it right at times. Signing a relatively unknown Luka Modric at the time for £16.5m and selling him to Real Madrid for double that can be regarded as a success. Likewise, paying £7m for Gareth Bale and then turning it into £85m when Real Madrid came calling is to be also applauded, but these clever dealings are accompanied by some truly horrific decisions on the whole. These same decisions are something the likes of Antonio Conte, who has been featured in the latest football betting tips and predictions already this season, will need to keep in mind moving forward, particularly if the club is to progress onto the next level and win some long-awaited silverware. Both Conte and Fabio Paratici will need to plan their moves wisely if Spurs are to avoid another wave of failed transfers.  

To swiftly remove any optimism you might have had around Spurs’ future transfer dealings, let’s take a look at some of the past mistakes the club has made when acquiring players. Here’s hoping lessons have been learned!  

Sergei Rebrov 

Kicking things off with one of the biggest flops in Premier League history, let alone Tottenham’s recent past, Sergei Rebrov only managed to bag 10 goals in 59 Premier League appearances during his time at the club – a disappointing return for a player who formed one of the great strike partnerships in European football at Dynamo Kyiv alongside Andriy Shevchenko. Perhaps it was the style of play or his inability to settle in England’s top flight, but Rebrov was a disaster.  

Roberto Soldado 

Another striker with plenty of promise after signing for the club from Valencia for a fee of £26m, Roberto Soldado’s effort generally couldn’t be faulted during his time at the club, but his goalscoring ability certainly could be. Given the fact that he was brought in to do just that, Soldado’s return of just 7 goals in 52 appearances is nothing short of an embarrassment.  

David Bentley 

David Bentley’s inclusion on the list might appear harsh to some, but the fact that his undoubted ability ultimately culminated in only 62 matches during a five-year stay at the club cannot be ignored. Bentley cost a staggering £17m at the time, which came with undoubted pressures also, something he perhaps struggled to deal with on the whole. The fact that Bentley went on to retire from football in 2013 aged just 29 and citing his hatred of modern football for doing so indicates that he was never going to fit in at a club aiming for the top. Still, his goal in the north London derby was good, wasn’t it?

Grzegorz Rasiak 

There’s a trend developing here and it is indeed that Spurs have had a rotten record when it comes to recruiting strikers over the years. Thankfully, Harry Kane is making up for it these days, but before the England striker the likes of Grzegorz Rasiak were being snapped up in an attempt to improve the clubs’ fortunes. The Polish striker was signed with a couple of minutes left on transfer deadline day in August 2005 and failed to score a single goal during his time at the club, before eventually being sold to Southampton.  

Bongani Khumalo 

Bongani Khumalo was with Tottenham between 2011 and 2015, but failed to make a single appearance for the club during his stay at Spurs. Loan moves hindered his chances of staking a claim somewhat but the fact that not one manager fancied him during his time at the club suggests that Khumalo was indeed out of his depth.  

Other horrific acquisitions include the likes of Paolo Tramezzani, Ilie Dumitrescu, Mbulelo Mabizela, Helder Postiga, and Calum Davenport.  

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