Tottenham chairman Daniel Levy is famed for his negotiating skills – but his determination to drive a hard bargain has led to some missed opportunities over the years.
There have been other reasons for failed transfers over the years, of course, but Spurs’ desire to be self-sustaining was certainly one of the reasons behind their failure to sign a single player in the summer of 2018.
It wasn’t the first time supporters have been left disappointed…
Andre Villas-Boas had identified Anzhi Makachkala winger Willian as one of the players capable of filling the gap left by Gareth Bale, with the Brazilian completing a medical ahead of a £30million switch.
However, Roman Abramovich made a few calls to fellow oligarch Suleyman Kerimov – the Anzhi owner – and Willian was suddenly heading to Chelsea, with Spurs left reeling and accusing the Blues of only signing Willian as part of a personal vendetta.
Erik Lamela did sign that summer, for a club-record £25million, but though he has shone at times, it’s fair to say Willian has been a rather greater success across London at Stamford Bridge.
Still, Spurs also signed Christian Eriksen that summer, which didn’t work out too badly…
Despite getting an hour’s extension past the transfer deadline in order to complete the transfer of Moutinho from Porto, Spurs could not get the deal over the line.
He was a principal target of Villas Boas’ after Luka Modric had been sold. A fee of £24million and personal terms were agreed, but the deal couldn’t be completed before the deadline.
“We were covered for the fact it could not happen bearing in mind it was a difficult club to deal with and would have been a club record fee,” Villas Boas said.
“We have cover enough and Moutinho’s transfer not happening should not overshadow that we got one of the biggest coups of the transfer market with (Clint) Dempsey.”
Spurs had, at least, signed Mousa Dembele a couple of days beforehand, which worked out pretty well.
Spurs had three bids rejected for Berahino in the 2015 summer, the last of which was worth £23million.
Berahino had handed in a transfer request at West Brom, but the club famously refused to back down, with the striker threatening to go on strike, before the start of his infamous decline and now two-and-a-half-year long goal drought.
Tottenham, meanwhile, couldn’t find an alternative so late in the window and did not sign a centre-forward until the following summer when Vincent Janssen arrived from AZ Alkmaar.
He only scored six goals in his first season at White Hart Lane – but that was still six more than Berahino managed.
Pochettino wanted a quick, right-sided attacker – you could say he still does – and Spurs were linked with the manager’s former Southampton man Sadio Mane.
Mane apparently visited the Spurs training ground and was set to move, only for Daniel Levy to baulk at the £36million fee and £90k-a-week wage demands.
Levy was, however, happy for Spurs to spend £30million on Moussa Sissoko…
Spurs’ interest in Brazilian striker Leandro Damiao became a long-running joke.
Linked with him every transfer window for about three years, he was expected at Tottenham due to an apparent sporting partnership with his club Internacional – Sandro had made the same move prior.
It never happened, but Damiao did eventually move to Europe, spending half a season on loan at Real Betis in which he made only three La Liga appearances and failed to score once.
Not only did Tottenham nearly sign Stewart Downing in 2008 and 2009, with the club going back in when they were just mid-table in January, they also nearly parted with Gareth Bale in the process.
Harry Redknapp tried to sign Downing, and the winger handed in a transfer request, but Middlesbrough rejected two Spurs offers.
Downing eventually joined Aston Villa in the summer of 2009, while Redknapp did what he does best and signed Niko Kranjcar.
Having reportedly also rejected both Manchester clubs, Hazard claimed he had considered an approach by Spurs in 2012 but decided against it after they dropped out of the Champions League.
“It’s true that Tottenham tempted me because it was a young team which was third in the league,” Hazard said.
“Unfortunately, the end of the season did not go well. They did not reach the Champions League, which tipped the balance.”
Spurs signed Gylfi Sigurdsson and Clint Dempsey that summer in their long pursuit of a No.10 before well and truly solving their creativity problems when they signed Eriksen the following year.
Rivaldo had been made available for a free transfer as Barcelona looked to cut their wage bill in 2002, with Levy flying out to Spain in an attempt to court the Brazilian.
“This illustrates the high nature of our ambition and the fact that we prefer to operate away from the spotlight,” manager Glenn Hoddle said. “Unfortunately, it didn’t happen this time, but the search goes on.”
Rivaldo chose to join AC Milan, and Hoddle said he even received a letter from the forward explaining his decision.
Spurs did sign another world class out-of-contract playmaker that summer at least: Milenko Acimovic…
With Aston Villa in a financial struggle, Spurs pushed their resolve to the limit with bids for England under-21 international Grealish, which never met the valuation.
Reportedly Steve Bruce and Villa were asking for upwards of £30million for the midfielder, with Spurs tabling bids around the £25million mark.
Having focused all their attention on Grealish, Spurs failed to make a signing in the summer of 2018, becoming the first Premier League club to do so in the history of the summer window.