From Jack Grealish and Bruno Fernandes to Eden Hazard and now Luis Diaz – Tottenham have been linked with big transfer but once again are set to miss out
Missing out on the signing of Luis Diaz will stir up some all-too familiar sad memories for Tottenham fans.
Spurs appeared to be front-runners to sign Porto winger Luis Diaz, however, the Colombian has decided to sign for Liverpool instead.
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Time will tell on whether Diaz is a hit for Liverpool, although their transfer business under Jurgen Klopp’s management suggests he’ll be a hit at Anfield.
And if that happens, Spurs will only be able to look on jealously as Diaz potentially tears it up at Liverpool and adds to their silverware collection.
But Spurs have been here before having missed out on some truly top players in the past.
talkSPORT.com picks out SEVEN stars they came oh so close to signing.
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Rivaldo
The appointment of Daniel Levy as Spurs chairman in 2001 was supposed to mark a new era for the club but instead it was actually a sign of things to come regarding their transfer market shortcomings.
In 2002, they were linked with one of the world’s best in Rivaldo, who netted five goals at the South Korea and Japan World Cup, which Brazil won. He had also lifted the Ballon d’Or three years before.
Many clubs were interested as he departed Barcelona but it then became between Spurs and AC Milan for Rivaldo’s signature, with Levy understood to have flown out to Sao Paulo to try and convince him to sign.
Rivaldo opted to join Milan instead, with then-Spurs boss Glenn Hoddle saying the Italian giants “pushed the boat out and pushed the money up to extortionate levels.”
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Ruben Dias
Another Primeira Liga talent slipped away from Spurs not too long ago and is now a Premier League hit.
Transfer guru Fabrizio Romano said: “Ruben Dias was really ready to join Tottenham. He also had ready, an agreement on personal terms with Tottenham. So, if Tottenham had found an agreement with Benfica, Ruben Dias was a Tottenham player – they were focusing on [Milan] Skriniar.
“He was really close to Tottenham because Mourinho persuaded him but was not the first choice and that’s it.”
Dias enjoyed an excellent first season at the Etihad, winning the Premier League and Carabao Cup in 2020/21, as well as the Premier League Player of the Season award.
Bruno Fernandes
In a parallel universe, Spurs would’ve also had Dias’ Portuguese compatriot Bruno Fernandes, who was itching to join the north London club in the summer of 2019.
However, like when they missed out on Dias, chairman Daniel Levy couldn’t agree a price with Fernandes’ club Sporting Lisbon and the move collapsed.
Any hope of Spurs trying again were all-but diminished when Mauricio Pochettino lost his job as head coach and was replaced by Jose Mourinho, who wanted to prioritise their defensive options in his first transfer window.
Fernandes ended up joining Manchester United in January 2020 and became an instant fan favourite at Old Trafford.
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Joao Moutinho
Going back a few years again but Spurs missed out on yet another top player from Portugal in Moutinho – the player revealing he was ‘minutes’ away from signing in August 2012.
However, the transfer didn’t go through as paperwork for the deal wasn’t submitted to the Premier League on time. Moutinho then joined Monaco a year later.
Moutinho was part of the Portugal side that won Euro 2016 and also helped Monaco to winning Ligue 1 in his final season at the club.
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Jack Grealish
Darling of Euro 2020 Grealish was also on the verge of signing for Tottenham but the deal fell through at the eleventh hour, all for the sake of £5million.
In the summer of 2018, Spurs had a £25m bid rejected by Grealish’s club Aston Villa, who were in the Championship at the time.
Villa demanded £30m for their captain but Levy decided not to pay it so that was that.
Levy may end up kicking himself as Villa sold Grealish to Manchester City for £100m, a Premier League record, last summer.
Eden Hazard
It’s never nice missing out on a player who then goes on to enjoy a great career for someone else. It stings a lot more when that club is a rival of yours.
Chelsea were the ones to enjoy the best of Hazard, who had seven glorious years at Stamford Bridge, the main highlights seeing him win the Premier League on two occasions and scooping the PFA Player of the Year award in the 2014/15 season.
But then-Spurs boss Harry Redknapp met with Hazard, who was playing for Lille at the time, and the Belgian seemed keen on the idea of a Spurs move in the summer of 2012.
However, Hazard opted to join Chelsea with their Champions League triumph in just weeks earlier, which also denied Spurs a route into the following season’s competition, proving to be the decisive factor.
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Willian
By no means the best player Spurs have missed out on but the way in which it happened is what hurts the most.
The Brazilian was all set to sign on the dotted line as he passed a medical at Spurs. Chelsea had other ideas.
As soon as he heard the west Londoners’ interest was concrete, Willian decided to ditch Spurs and once again it was the west Londonders who benefited.
If it’s any consolation, Willian had a poor spell at Spurs’ north London rivals Arsenal, where he served just one year of the three-year deal he signed.
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