From Jack Grealish and Bruno Fernandes to Eden Hazard and now Luis Diaz – Tottenham have been linked with a big transfer but once again they should miss out

Missing out on signing Luis Diaz will bring back sad memories all too familiar to Tottenham fans.

Spurs appeared to be the first to sign Porto winger Luis Diaz, however, the Colombian decided to sign for Liverpool instead.

Time will tell if Diaz is a success for Liverpool, although their transfer activity under Jurgen Klopp suggests he will be a success at Anfield.

And if that happens, Spurs will only be able to watch jealously as Diaz potentially rip him apart at Liverpool and add to their collection of silverware.

But Spurs have been here before missing out on some of the best players in the past.

talkSPORT.com picks SEVEN stars they’ve come so close to signing.

Rivaldo

The appointment of Daniel Levy as Spurs chairman in 2001 was supposed to mark a new era for the club, but it was actually a sign of things to come regarding their shortcomings in the transfer market.

In 2002, they were linked with one of the best in the world in Rivaldo, who scored five goals in the South Korea and Japan World Cup, won by Brazil. He had also lifted the Ballon d’Or three years before.

Many clubs were interested when he left Barcelona, ​​but it then became between Spurs and AC Milan for the signing of Rivaldo, with Levy believed to have flown to Sao Paulo to try and convince him to sign.

Rivaldo opted to join Milan instead, with then-Spurs boss Glenn Hoddle claiming the Italian giants “pushed the boat and pushed the money to exorbitant levels”.

Ruben Dias

Another Primeira Liga talent escaped Spurs not too long ago and is now a Premier League success.

Transfer Guru fabrice romano said: “Ruben Dias was really ready to join Tottenham. He was also ready, a deal on personal terms with Tottenham. So if Tottenham had reached 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 wasn’t the first choice and that was 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 an alternate universe, Spurs would also have had Dias’ Portuguese compatriot Bruno Fernandes, who was eager to join the north London club in the summer of 2019.

However, like when they missed out on Dias, chairman Daniel Levy could not agree a price with Fernandes’ club Sporting Lisbon and the move fell apart.

Any hope of Spurs trying again was all but dimmed when Mauricio Pochettino lost his job as head coach and was replaced by Jose Mourinho, who wanted to prioritize their defensive options in his first transfer window.

Fernandes ended up joining Manchester United in January 2020 and became an instant fan favorite at Old Trafford.

Joao Moutinho

It was just a few years ago that Spurs missed out on another top Portugal player in Moutinho – with the player revealing he was minutes away from signing in August 2012.

However, the transfer didn’t go through as the deal documents weren’t submitted to the Premier League on time. Moutinho then joined Monaco a year later.

Moutinho was part of the Portuguese team that won Euro 2016 and also helped Monaco win Ligue 1 in his final season at the club.

Jack Greish

Euro 2020 darling Grealish was also close to signing for Tottenham but the deal fell through at the eleventh hour, all for £5million.

In the summer of 2018, Spurs had a £25million bid rejected by Grealish’s then-League side Aston Villa.

Villa demanded £30m for their captain but Levy decided not to pay him, so that was it.

Levy could end up kicking himself as Villa sold Grealish to Manchester City for a Premier League-record £100million last summer.

Eden Hazard

It’s never nice to miss out on a player who then pursues a great career for someone else. It stings a lot more when this club is a rival of yours.

Chelsea were the ones to take advantage of the best of Hazard, who spent seven glorious years at Stamford Bridge, with key highlights seeing him win the Premier League twice and win the PFA Player of the Year award in the season. 2014/15.

But then-Spurs boss Harry Redknapp met Hazard, who was playing for Lille at the time, and the Belgian seemed keen on a move from Spurs in the summer of 2012.

However, Hazard opted to join Chelsea with their Champions League triumph a few weeks earlier which also left Spurs out of the following season’s competition, which proved to be the deciding factor.

Willian

By no means the best player Spurs have missed out on, but the way it happened is what hurts the most.

The Brazilian was ready to sign on the dotted line as he underwent a medical at Spurs. Chelsea had other ideas.

As soon as he heard there was concrete interest from West Londoners, Willian decided to drop Spurs and once again it was West Londoners who benefited.

If it’s any consolation, Willian had a bad spell at Spurs’ north London rivals Arsenal, where he served just one year on the three-year contract he signed.