Fair to say, Tottenham Hotspur have made a fair few mistakes in the transfer market throughout their history. Some of the best players in the world have called N17 home in recent decades, but Spurs certainly do not boast the silverware to reflect this.
Now, for the purpose of this, none of those players have been included in this list. It would be stating the obvious to suggest that Spurs would have been better off had they held on to Harry Kane, Gareth Bale, Luka Modrić, Kyle Walker, Dimitar Berbatov, Glen Hoddle and others who left in their prime. This listicle documents genuine mistakes Spurs made in the transfer market, allowing players to leave when they really shouldn't have for various reasons.
Troy Parrott
The first player on this list is all the most recent. Earlier this season, Troy Parrott was the most popular man in Ireland, after his double against Portugal and then hat-trick in Budapest against Hungary snatched a World Cup play-off spot for the Boys in Green. Briefly, Dublin airport was jokingly renamed Troy Parrott International Airport, but how has he been getting on at club level?
Well, after joining Tottenham as a teenager, he was loaned out to Millwall, Ipswich, Milton Keynes, Preston and Excelsior, appearing just four times for Spurs' first-team. His final loan in Rotterdam, scoring 17 times, convinced AZ Alkmaar to pay £6.7 million to recruit him permanently which, at the time, appeared to be excellent business for Spurs.
Nevertheless, AZ are likely to see a sizeable return on investment, given that Parrott has scored 49 goals in 91 appearances for the Cheese Farmers, averaging a goal every 140 minutes. 29 of these goals have come this season, and he could make himself even more of a hero with AZ set to take on NEC Nijmegen in the KNVB Beker Final at De Kuip, seeking major silverware for the first time since 2013. With Parrott likely to earn a big money move back to the Premier League, did Spurs cash in too early; given their trials and tribulations throughout this season, he surely could have contributed?
Mousa Dembélé
Looking back at happier times for Tottenham Hotspur supporters, what a player Mousa Dembélé was. The Belgian arrived from Fulham in August 2012 for £15 million, going on to make 249 appearances for Spurs during the most successful period of the club's modern history.
Widely considered one of the most underrated players in Premier League history, Dembélé's style was pretty unique, impossible to dispossess and a generally all-round magnificent midfield player. So, did Spurs sell him too early? At the age of just 31, he joined Chinese Super League outfit Guǎngzhōu R&F for a reported £11 million in January 2019.
He had only made 13 appearances during the first half of that campaign due to thigh and ankle issues, so was clearly no longer at the peak of his powers. Nevertheless, it is impossible to feel as though he had more left to give, especially considering Mauricio Pochettino's team would make it all the way to the Champions League Final a few months after his departure. Despite that run to Madrid, Spurs suffered a sharp decline in 2019 and beyond, with Dembélé's sale signifying the start of this.
Rafael van der Vaart
Looking back at Tottenham's first-ever Champions League campaign under Harry Redknapp in 2010/11, Rafael van der Vaart was the undisputed star. He arrived that summer on deadline day, after a move to Bayern Munich had fallen through, and would become an instant cult hero at White Hart Lane. He netted against both Twente and Inter as Spurs reached the Champions League quarter-finals, bagging 13 Premier League goals during his first campaign and 11 the year after.
However, following only two seasons in N17, he re-joined Hamburg, where he would continue to showcase his quality at die Rothosen. Ultimately, van der Vaart was a Tottenham player for a good time not a long time, so there must be a sense of regret that fans did not get to enjoy him for longer.
Peter Crouch
From the same era, Peter Crouch was not at Tottenham for as long as one might think either. Having been sold to QPR for £60,000 as a teenager, the striker re-joined Spurs from Portsmouth nine year later, reuniting with Redknapp. He famously scored the last-gasp winner at Manchester City that secured a top four finish, before netting seven times during Spurs' subsequent Champions League run, including the only goal of the tie at San Siro as they dumped out AC Milan in the round of 16.
Overall, Crouch made just 93 appearances for Spurs, before being sold to Stoke in the summer of 2011 for £12 million, the Potters' club-record fee at the time. This was obviously a good amount of money for Tottenham, but Crouch would go on to make 261 appearances in the Potteries, scoring 61 goals, of which 14 came during his debut campaign, suggesting he had more to give had he continued in North London.
Frédéric Kanouté
Going back further into history, Spurs had one of the best strikers in Europe on their hands, they just didn't know it yet. In the summer of 2003, Freddie Kanouté made the controversial move across the capital from West Ham to Tottenham, costing £3.5 million following the Hammers' relegation. The Malian scored a respectable 21 goals in 73 appearances for the club, of which 14 came in the Premier League, but doing little to foreshadow how good what he would become.
Thus, he was sold to Sevilla for €6.5 million in the summer of 2005, where he would become a legend. Kanouté scored 136 goals in 289 outings for los Nervionenses, winning two Copa del Reys and two UEFA Cups. He netted against Middlesbrough during the 2006 final in Eindhoven and again as los Hispalenses defeated Espanyol at Hampden 12 months later, as well as being the match winner in the 2007 Copa final against Getafe at the Bernabéu.
Overall, he became one of the most feared strikers in all of Europe, bagging 21 La Liga goals in 2006/07, 16 the following year and then 18 the campaign after that. While Sevilla were starting their period of glory, Spurs were in decline, so had Kanouté been convinced to stay in North London, who knows if he would have reached his full potential, but he certainly feels like one that got away.
Add us as a preferred source on Google