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5 times Tottenham Hotspur missed out on transfer targets

Scott Newman
Top 5 / Top 10

Aston Villa v Reading - Sky Bet Championship
Current reports suggest that Tottenham are going to miss out on the signing of Jack Grealish

With just over a week to go before transfer deadline day, fans of Tottenham Hotspur have been left largely unhappy with the apparent news that the Lilywhites are about to miss out on their primary target this summer – Aston Villa attacker Jack Grealish.

Current reports suggest that although Grealish would like to move to Spurs, a formal bid for the player has not yet been tabled, probably because Tottenham chairman Daniel Levy was banking on getting him cheaply due to Villa’s financial issues – issues that ended when billionaires Nassef Sawiris and Wes Edens decided to invest in the club – and now Villa simply don’t need to sell as badly.

If Tottenham do indeed miss out on Grealish, it won’t be the first time the North London side have missed out on an important signing. Here are 5 other major players who Spurs missed out on signing.

#1: Willian

Chelsea v Crystal Palace - Premier League
Willian almost became a Tottenham player in 2013

A lot of the time, the frugal nature of Tottenham chairman Daniel Levy is blamed when the Lilywhites miss out on a key transfer target, but in the case of Brazilian winger Willian, it wasn’t Levy’s fault at all – and was more down to somewhat questionable morals from the player and his agents, as well as some clever networking that hijacked the deal.

It was the summer of 2013 and thanks to the sale of Gareth Bale to Real Madrid for £85m, Spurs had a ton of money to splurge. They’d already broken their transfer record twice – for Paulinho and Roberto Soldado – and fans were excited when the club became linked with Willian, who was playing for Russian side Anzhi Makhachkala. A fee of £30m was apparently agreed, and so the Brazilian made his way to White Hart Lane to complete a medical.

Suddenly though, the situation turned on its head when Chelsea made their interest in the player known. Blues chairman Roman Abramovich apparently made a call to his friend Suleyman Kerimov – chairman of Anzhi – and two days later, for a slightly larger fee, Willian was a Chelsea player.

With Chelsea boss Jose Mourinho taunting Spurs about how they “should’ve done the medical in secret”, everyone from then-Spurs manager Andre Villas-Boas to Levy was furious. For once it was a missed opportunity due to no fault of Tottenham’s own – made even worse when Willian claimed he was “fulfilling a dream” by moving to Stamford Bridge.

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