Tottenham Hotspur have signed a number of incredible talents over the years, while bringing a good few more through the academy in North London.
Some, like Gareth Bale and Luka Modric, arrived as relatively unknown names, before leaving as two of the most famous and successful stars in world football.
Others, like Rafael Van der Vaart were signed in their prime in order to get bums off seats at White Hart Lane over the years.
Two current first-team stars, Harry Kane and Harry Winks, each came through the academy system, meaning that Spurs didn’t have to pay a penny in transfer fees.
However, while Spurs have certainly had their success stories over the years, The Athletic have now outlined some of the most mouth-watering deals that didn’t quite happen for the Lilywhites.
Rivaldo – ‘Word soon got round that one of the best players in the world was available on a free transfer. Tottenham, at the time, had just finished ninth in Glenn Hoddle’s first full season in charge and had been taken over by ENIC a year earlier. New chairman Daniel Levy was keen to issue a statement of intent and make a big signing to illustrate the size of his and Tottenham’s ambition. Hoddle, a supremely gifted technician himself, was understandably thrilled by the prospect of bringing in a player of Rivaldo’s quality. It’s fair to say he would have been a pretty decent upgrade on Steffen Iversen. In the end though, despite Levy’s best efforts, Rivaldo opted to join AC Milan.’
Manuel Auset, Rivaldo’s close friend and lawyer at the time, added: “Tottenham offered him the chance to play in the Premier League and there was a meeting with me, an agent and Mr Levy. The first meeting with Tottenham was in Sao Paulo and then in London after the World Cup. There were a few interested clubs — we even had a conversation with Florentino Perez, the Real Madrid president, but Rivaldo gave his word to Barcelona that he wouldn’t go to Real Madrid. Then it was either Tottenham or Milan. Milan sent representatives to Sao Paulo and we arrived at an agreement but didn’t sign it. Then we went to Milan, spoke about it there, and reached an agreement.”
Fernando Morientes – ‘Finally, after hours of negotiations between Levy and Jorge Valdano, Real Madrid’s then sporting director, it is understood that a fee of around €10 million (£8.9 million by today’s exchange rate but between £6 million and £7 million at the time) was agreed. It was at this point, according to a source close to the deal, that Levy asked that Spurs pay the amount in instalments, over a 10-year period. A furious Valdano is said to have put the phone down shortly after this suggestion and the deal was dead.’
Nuno Gomes – ‘Portugal striker Nuno Gomes was tempted to join from Fiorentina but in the end, he chose to return to Benfica in his home country’. The forward told The Athletic: “There were negotiations between the two clubs but they didn’t reach an agreement. My preference at the time was to return to Benfica but it was possible I would have moved to England if they had struck a deal. I knew Tottenham was a good club.”
Samuel Eto’o – ‘Samuel Eto’o was another centre-forward linked at that time with Spurs and other English clubs, but none were willing to take a punt on the 21-year-old, who was then at Real Mallorca.’
Cristiano Ronaldo – Ex-Spurs striker and talent-spotter, Ronny Rosenthal told The Athletic: “I saw Cristiano Ronaldo because I started going a lot to Portugal. I told clubs to come and watch him and recommended Ronaldo to Arsenal, Tottenham and others. They didn’t follow it up.”
Diego – ‘He was one of the stars of an excellent young Santos side also including Alex, Robinho and Elano who won the Brazilian title the previous year. His performances for Santos earned him the nickname ‘Zidane Jr’ and led to two bids from Tottenham that August — the second of which was worth around £7.6 million.’
His father, Djair Ribas, told The Athletic: “The contact was through a person in London, who knew one of the Tottenham directors. Diego was very young at the time, just starting out. He was following the situation but he also wanted to stay focused on his work at Santos. There was an offer. It came to us and we presented it to Santos. But we didn’t reach an agreement because the value was too low and the payment was spread over a long period. In the end, we decided that it wasn’t what we were looking for. Diego wasn’t sad about it at the time. I thought it was a good option because I like English football but they were the first club who contacted us and we knew that there would be plenty of others. So it proved.”
Theo Walcott – ‘Spurs were one of many interested parties and made inquiries but Arsenal’s double act of manager Arsene Wenger and vice-chairman David Dein charmed Walcott’s parents and convinced them that Highbury was the best possible destination for their son. Tottenham were also coming out of a turbulent period with frequent managerial changes, whereas their neighbours and arch-rivals could offer far more stability and pedigree at the time.’
Damien Duff – ‘A deal looked close but in the end, Duff decided to join Newcastle instead.’
Duff said: “I remember getting a message from Martin Jol but I was a Chelsea fan after winning titles there, so it was something I never really looked at. I had friends at Newcastle — Scott Parker, Shay Given — and I wanted to give that a real go.”
Stewart Downing – ‘One of the near-misses, in Redknapp’s first window, was then-Middlesbrough winger Stewart Downing. Middlesbrough were determined to hold onto the player and wouldn’t countenance a deal, even when Spurs reportedly went as high as £14.5 million.’
Luis Suarez – ‘It should be said that it was not a deal that ever got especially close but imagining him playing for Spurs is another agonising counterfactual. As it turned out, Redknapp did not see Suarez as a true striker, which was what he felt the team needed at the time, and so decided against pursuing the Uruguayan ahead of the January 2011 window, when he joined Liverpool from Ajax.’
Redknapp said: “Luis Suarez was a player I liked a lot. He was presented to me but the people at the club who’d seen him and liked him though he played off the left, whereas I was looking more for an out-and-out striker. I wasn’t looking for a left-winger as such and before I’d had a chance to do much with him, he’d moved to Liverpool. Not that I’m saying we would have definitely got him.”
Gary Cahill – Redknapp said: “Cahill I chased, and we could have got him — he was cheap,” Redknapp says. “We should have taken him. But I don’t think Daniel (Levy) could do a deal with the Bolton chairman, for whatever reason. When you’re managing, you hand it over and hope the deal gets done.”
Eden Hazard – Then Spurs first-team coach Clive Allen said: “It (that window) is a regret, yeah. Had it been different, it might have kept me and Harry in a job. Around that time, we could have got Eden Hazard. I went over to France and met him in a hotel in Paris. The chief scout and I met with Hazard and he was keen to come to Tottenham at the time but, in the end, he decided to join Chelsea. I was confident it would happen and he definitely would have come to Tottenham. I loved him. I mean, what a player. Joe Cole rung me — he was at Lille at the time — and said he was the best player he’d ever played with. I said, ‘That’s some statement, Joe’, and we went over there straight away, had a meeting with the player, went to a couple of games; though once you’d seen him once, you knew. He was just fantastic, an incredible player.”
Joao Moutinho – ‘Now at Wolves and then of Porto, was the one who came closest to joining after Spurs identified him as their preferred successor to Luka Modric and had a bid of around £24 million accepted. But Tottenham just couldn’t get the deal completed in time and as August slipped into September, they had to admit defeat.’
A source close to the deal told The Athletic: “The transfer didn’t happen because everyone ran out of time. It started that morning and it was an intense day. If there had been one more hour in the day, he would have signed.”
Leandro Damiao – ‘It came down to Spurs and Damiao’s club, again Internacional, being drastically apart in their valuations of the player. A dialogue that started in 2011 continued throughout 2013 but Luigi says although there were many conversations and it was known that Damiao had a buyout clause of £17.8 million, Tottenham never actually put an offer in writing.’
Internacional’s then-president Giovanni Luigi told The Athletic: “Yes, we did have talks with Tottenham. I spoke with their chairman (Levy) twice on the phone. He was talking about an offer of €8 million (£7.12 million) or €9 million (£8.01 million), which was much lower than what we had in mind. I had the feeling that they expected us to accept their offers just because it’s Brazil.”
Pierre-Emerick Aubameyang – ‘Tottenham were not the only club to say no, as Arsenal and even Borussia Dortmund, who he joined a year later in 2013, also declined to buy a player who was available for around £10 million (he has since accumulated transfer fees of close to £70 million). Ronny Rosenthal was working with Aubameyang at the time and has a picture of the striker in what appears to be the Spurs dressing room in front of a shirt with (Aaron) “Lennon 7” on the back.’
Aubameyang said five years later, “(In 2012), I was in Tottenham at the time, looked at the stadium and the training ground, and we talked,” he said. “But after that, nobody contacted me again.”
Rosenthal revealed: “Villas-Boas didn’t fancy him. He just didn’t see what was to come. No one wanted him then. In football, the point is to see what’s coming in the future and if they don’t see what’s coming in the future, they won’t do anything. The big clubs have more choice, and it happens a lot. Some at the club did want Aubameyang but once Villas-Boas said not for him, that was the end of it.”
Henrikh Mkhitaryan: ‘The then 24-year-old flew to north London to meet with representatives from White Hart Lane — as often happens with clubs and prospective signings. But in the end, Mkhitaryan was persuaded by Jurgen Klopp to join Dortmund as a replacement for Mario Gotze, who had left them to join Bayern Munich.’
Willian – ‘It was a summer almost as notable for the players they missed out on, most famously Willian, who completed a medical only for Chelsea to hijack the deal at the very last minute. Spurs were enraged by what they saw as foul play and Levy was said to be incandescent. Some at the club even believed Chelsea had signed the player simply to spite Tottenham and that it represented a vendetta they held against their cross-London rivals.’
Hulk – ‘In 2013, Tottenham were willing to go up to around £30 million for the striker but Zenit were holding out for closer to the £39 million they had paid Porto for Hulk the previous summer. Spending that kind of money on a 27-year-old was out of reach for Tottenham then.’
Anthony Martial – ‘At the end of that campaign, he is understood to have visited the Tottenham training ground and had contact with Pochettino. But Manchester United, desperate to strengthen their squad after a sluggish start to their 2015-16 season, made their move on transfer deadline day. The fee of £36 million was a world record for a teenager and had the potential to rise as high as £58 million — figures that Tottenham simply could not match.’
Virgil Van-Dijk – ‘Had Levy failed to get Alderweireld then Van Dijk, then at Celtic, is understood to have been the next name on the list of centre-back targets.’
Dayot Upamecano – ‘Spurs’ scouts raved about his athleticism and ball-playing after watching him star for France at the Under-17 European Championship in Bulgaria, and he was deemed perfect for the Pochettino project. Tottenham very rarely buy players at that age, preferring to trust those who have been nurtured in their academy, but with the compensation only expected to be just over £300,000, he was deemed to be a relatively low-risk option. But in the end, Spurs lost out to the financial might of the Red Bull organisation. Red Bull Salzburg were willing to pay a much higher transfer fee and wages than Spurs and even other interested clubs like Manchester City, and so he moved from France’s Valenciennes to Austria at the end of the 2015-16 season.’
Max Kruse – ‘Aged 27 and attainable for around £10 million, the Germany international was a viable option but there were concerns about his professionalism and dedication. A year later, he was dropped from the national team after a string of misdemeanours.’
Danny Ings – ‘Pochettino was a fan of and is believed to have had contact with at the time (Ings also met with David Moyes, then at Spain’s Real Sociedad). Ings was 22 and available on a free, with around £10 million owed to his club Burnley as compensation, but Tottenham always felt as though he had his heart on a move to Liverpool.’
Saido Berahino – ‘Tottenham insisted they made an offer that met West Brom’s £25 million asking price but West Brom chairman Jeremy Peace refused to budge. As the deal became, according to sources, a battle between the rival egos of Levy and Peace, Berahino tweeted that he would never play for West Brom again.’
Kylian Mbappe – ‘Kylian Mbappe appeared on their radar when he came on as a second-half substitute for Monaco against them in the Europa League in December 2015. The 16-year-old quickly registered an assist and scouts were sent to France to take a closer look at him. It soon became apparent though that Mbappe would be out of their reach — Tottenham were informed there was already interest from Real Madrid but that the youngster’s plan was to sign a professional contract at Monaco first to try to establish himself there. Had he not, he would have been available for around £450,000 in compensation, but his desire to stay in France meant a deal was impossible.’
Ousmane Dembele – ‘There had been suggestions of a buyout clause, but these proved to be wide of the mark and ultimately, close links between Rennes and Dortmund, who were both sponsored by Puma, saw Dembele join the Germans at the end of the season. Complications over who represented Dembele also put Tottenham off pursuing the deal.’
Sadio Mane – ‘Another from Southampton who had worked with Paul Mitchell when he was at St Mary’s. Mitchell had already helped to sign him at Southampton so was familiar with the agents involved, while the way Mane had forced that move offered hope that he was testable. Continuing the theme of being outbid by a rival, however, Liverpool came in with an offer of a £34 million and wages of around £90,000 a week. Spurs did end up paying £30 million for Moussa Sissoko a couple of months later but that was a very different deal as the payments were staggered and it was a signing completed on deadline day, with Newcastle expecting to sell the midfielder during the window.’
Wilfried Zaha – ‘Tottenham bid £12 million for Wilfried Zaha, which was dismissed as “ridiculous” by his Crystal Palace chairman, Steve Parish. Zaha was a player Pochettino really admired but his long-term contract at Palace meant a deal is never thought to have been close. Spurs were similarly rebuffed for him in 2018 and then again the following year.’
Jack Grealish – ‘They tried and failed to sign Jack Grealish from Aston Villa, whose financial difficulties made them seem appear easy prey. An offer of £25 million was nowhere near what Villa were after, however, and according to one source, “they grew a pair of bollocks and stood up to it”.’
Paulo Dybala – ‘By the time the purse-strings were loosened last summer and Tottenham made serious moves to sign Paulo Dybala, Juventus decided at the last minute that the striker was not for sale. There were also issues over Dybala’s image rights, which feel a world away from the days of Rivaldo’s camp sending Hoddle that letter.’
Spurs Web Opinion:
It is extremely interesting to read the inside scoop on a number of these transfers. Unfortunately, an awful lot of luck comes in to play when it comes to some of these deals. While a £500,000 signing can become the next Mbappe, they can also be a complete flop. For me, the Dybala deal falling through certainly stings the most in recent years, especially after the Champions League Final defeat.
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