5 times Tottenham Hotspur missed out on transfer targets

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.

#2: Joao Moutinho

Derby County v Wolverhampton Wanderers - Pre-Season Friendly
Joao Moutinho could've signed for Spurs had it not been for Premier League regulations

Portuguese midfielder Joao Moutinho will be starring in the Premier League in 2018/19 for Wolves, after the Midlands club were able to secure his services for a cut-price £5m earlier this summer. Frustratingly for Tottenham fans though, Moutinho could’ve been a Premier League star way back in the summer of 2012 had the Lilywhites’ move for him not fallen through at the last minute on that summer’s deadline day.

On this occasion, Tottenham’s move fell foul of Premier League regulations regarding third party ownership of players. Moutinho’s club Porto were willing to sell, and were happy to accept Tottenham’s £24m bid for the player – who seemed happy with the move, as it offered him a chance to hook up with his former boss Andre Villas-Boas. But despite Moutinho stating that he was “minutes away” from being a Spurs player, the move fell through and he ended up spending another season at Porto before moving to Monaco.

The devil turned out to be in the details – of the £24m that Tottenham were offering, 25% of the profit was to go to Sporting Lisbon, who had sold Moutinho to Porto in 2010. That wasn’t a problem – but the fact that 15% was also to go to a “third party investor” who had bought a percentage of the player’s rights in 2011 ended up being a major stumbling block, with Premier League rules preventing any third party ownership in players.

Tottenham simply couldn’t sort the issue out in time, and so they ended up missing out on a player who could’ve become a key figure for Villas-Boas in 2012/13.

#3: Sadio Mane

Liverpool v Hull City - Premier League
Sadio Mane could've been a Spurs player had it not been for their frugal wage structure

Liverpool forward Sadio Mane has been tearing up Premier League defences for four seasons now, but while fans of the Reds have become accustomed to his flying attacking style and ability to score and create goals seemingly at will, the Senegalese star could have ended up a Tottenham player instead, had it not been for his large wage demands.

Reports emerged in early 2017 that suggested that in the summer of 2016, then-Southampton star Mane headed to Tottenham’s Enfield training ground to discuss a move, and a transfer fee of somewhere around £34m – the same fee that Liverpool eventually ended up paying for him – was discussed.

Unfortunately, Spurs chairman Daniel Levy wasn’t fully convinced that the services of Mane would be worth breaking the club’s infamously tight wage structure for. At the time, Tottenham’s highest earners were Harry Kane and Hugo Lloris, who were both reported to be on £100k per week. Mane’s demands were unknown, but recent reports from 2018 suggest he currently earns £90k per week at Liverpool.

While the possible move wasn’t reported at the time – thankfully for Levy as it probably would’ve drawn the ire of Spurs fans – it stands as an example of Tottenham missing out on a player who’s become a major star due to their tight finances.

#4: Dimitri Payet

France v Romania - Group A: UEFA Euro 2016
Dimitri Payet could've played under Harry Redknapp at Spurs

Currently plying his trade back in France with Marseille, Dimitri Payet rose to fame after a blistering 2015/16 season at West Ham that he followed with some equally brilliant performances for France during Euro 2016. But incredibly, had things gone slightly differently, the French maverick could’ve been a Tottenham player some 7 years before moving to West Ham – back in 2009 when he was just 21 years old.

In 2016 it was reported that Damien Comolli, who acted as Tottenham’s Director of Football from 2005 to 2008 – spanning the reigns of Martin Jol and Juande Ramos – had come close to signing Payet for Spurs, but ended up leaving the club before the move could be completed.

According to Comolli, he’d been contacted by French side St. Etienne in the summer of 2007, just as they were completing a £4m move to sign Payet from Nantes. The idea was apparently that St. Etienne would sell Payet to Spurs two seasons later for £10m – essentially when they felt he’d be Premier League-ready – but when Comolli was fired in the autumn of 2008, the idea went by-the-by.

In this case, it wasn’t really Tottenham’s fault that they missed out on such a great talent – Comolli had come under criticism for many of his signings and his dismissal seemed overdue at the time – but it certainly would’ve been fun for Spurs fans to see the maverick talents of Payet under Harry Redknapp in 2009/10!

#5: Saido Berahino

Chelsea v Stoke City - Premier League
Spurs missed out on Saido Berahino - and signed Heung Min Son instead!

After a terrible run of form that’s seen him score no Premier League goals since 2015/16, it’s easy to forget that a few years ago, Saido Berahino was hot property and came very close to sealing a move to Tottenham from West Bromwich Albion. The young England striker had scored 14 Premier League goals for West Brom in 2014/15 and so it was no surprise when Spurs looked to move for him that summer.

Unfortunately, the move never happened largely due to a similar situation as we’re currently seeing with Jack Grealish. Tottenham made a £15m bid for the player, but West Brom felt he was worth somewhere closer to £25m, and Spurs chairman Daniel Levy simply wasn’t willing to up the fee. And so despite going on a wild Twitter rant against his West Brom employers – namely chairman Jeremy Peace – Berahino never got his move to White Hart Lane.

Weeks later, Berahino was embedded into West Brom’s squad once again, and eventually Tottenham made a move for Bayer Leverkusen’s Heung Min Son instead, and the Korean arrived for a fee of around £22m.

Given Son’s success since – he’s already scored 47 goals for the Lilywhites and has become a cult favourite – and Berahino’s subsequent struggles, Spurs fans would probably count themselves lucky in this instance that they did miss out on the young Englishman. But had they signed Berahino, who knows what could’ve been for him?

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Edited by Sai Krishna