The tale of Morgan Gibbs-White in summer 2025 can take its rightful place in the legion of legendary transfer tales which could only happen to Spurs.
Every club has a long line of transfer sagas doomed to fail behind them, the granular details of which a fanbase can recite even as years pass and players and managers come and go.
But as ever with Spurs, theirs do feel slightly more uniquely absurd.
And triggering a player’s release clause only to be threatened with legal action before said target signs a lucrative new contract at his belligerent club feels like a fitting companion to these ludicrous stories from years gone by.
Leandro Damiao
While transfer rumours almost exclusively concern actual footballers, Spurs once found themselves constantly on the verge of signing a player whose existence beyond their gossip columns is yet to be conclusively proven.
The Daily Mail were responsible for prompting this experiment into transfer speculation frenzy in the social media age, linking Spurs with a £10million deal for a forward who had scored 53 goals in his first two seasons at Internacional by the summer of 2011.
The Brazilian club’s president Giovanni Luigi confirmed he “spoke with their chairman twice on the phone” years later, but “he was talking about an offer of €8 million or €9 million, much lower than what we had in mind,” which does not sound like Daniel Levy at all.
Fables of Sky Sports News erroneously reporting on Damiao boarding a flight bound for England on deadline day have been passed down through generations of long-suffering north Londoners but the real victim was a player whose entire career in Europe comprised of three games on loan at Real Betis.
Damiao finally fled Internacional in 2013 but not before enduring a fate no-one would wish on their worst enemy: being the subject of a bidding war between staring contest champions Levy and Napoli chief Aurelio De Laurentiis.
He is, in fact, still knocking them in occasionally for Coritiba as Thomas Frank weighs up whether to persuade a 36-year-old journeyman that the time to spread his wings beyond Brazil and Japan is now.
Joao Moutinho
Andre Villas-Boas requested David Villa, Hulk and Moutinho. He received Vlad Chiriches, Nacer Chadli and the rest of The Magnificent Seven.
It was the second summer in succession that club and manager were seemingly in agreement over one specific target. Villas-Boas perhaps felt he was due Moutinho after the fiasco of his attempted capture in 2012.
“We had massive, massive arguments in the beginning because of this with Moutinho,” the Portuguese coach would later say while slamming a recruitment model which placed the midfielder “sixth on the list compiled by data people”.
A club-record deal – the planned replacement for Luka Modric – collapsed while Spurs publicly championed the ‘coup’ of bringing in Clint Dempsey for significantly less.
Willian
The story oft-chanted by Chelsea supporters is that Spurs bought his flight before Willian saw the light, got the call from Abramovich and headed off to Stamford Bridge.
But the player himself has hardly been shy in discussing one of the great transfer hijacks of our time. Willian has said he was in London for two weeks “waiting for Tottenham to decide” before he finally underwent medical tests and the contract was presented to him.
Then Kia Joorabchian produced the curveball of contact from Chelsea.
Willian’s interest was sufficiently piqued but extricating himself from Tottenham’s training ground inevitably proved troublesome.
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“I stayed there for eight hours in the training centre. Tottenham’s director said ‘I’m going to report you to FIFA, this and that, fans here in England will boo you, this and that.’ They made up a lot of things,” Willian has since said, presumably while shining up the various trophies won in another part of London.
It is the one deal which caused Levy’s head to fall off most dramatically and almost certainly still rankles. He was ‘incandescent’ with ‘rage’ and privately insisted Chelsea didn’t even want Willian and had simply signed him because of their ‘vendetta’ against Spurs.
Jose Mourinho probably didn’t help things by blaming Spurs for not doing the medical “in secret”, before telling a press conference of guffawing journalists that Chelsea were not yet guaranteed to sign Willian because he still had to undergo a medical.
How strange that Mourinho and Levy’s professional union never worked out.
Emmanuel Petit
If Spurs had a pound for every time they covered the transport of a transfer target whose move was commandeered by a bitter rival, they would only £2 but it is weird and hilarious that it has happened twice.
Petit was destined to leave Monaco in summer 1997 but his destination was to be decided. The Frenchman spoke with clubs in Italy and Spain but a trip to London proved fateful.
“I had meetings on the same day with Tottenham and Arsenal,” began one of the great many occasions on which Petit has regaled a room of chortling old men with the tale.
“When I left the Spurs stadium, they booked me a cab and the cab driver asked me for directions, so I gave him the Arsenal address and I didn’t realise that the cab was pre-paid by Spurs, so they knew where I was going!”
A prior working relationship with Arsene Wenger meant middling Spurs had little to no chance of persuading the midfielder their half of north London was the superior choice. Petit ended the season as a World Cup and Premier League winner so fair enough.
Klaas-Jan Huntelaar
A brief mention for a player linked with Spurs frequently during their Barclays peak, with the best line from about four years’ worth of speculation produced by the otherwise entirely reliable and trustworthy News of the World:
‘Tottenham boss Harry Redknapp will fly out to Amsterdam to thrash out personal terms with Real Madrid striker Klaas-Jan Huntelaar, 25, after agreeing an £18m deal with the Spanish side.’
The Dutchman signed for Milan a week later.
Rivaldo
There is no better place to end than with the renowned letter sent by Rivaldo to N17, in which the fresh World Cup winner sought to outline why he chose to join actual AC Milan over Glenn Hoddle’s mid-table Spurs.
“We were so close to getting Rivaldo,” Hoddle said at the time in an address you can practically hear him delivering. “I’ve never known it before, he sent a terrific letter explaining why he opted for Milan. I’ve never had that before from a player I’ve missed out on.
“Milan pushed the boat out and pushed the money up to extortionate levels. Other than that we were pipped at the post – he was coming here.
“It was a touch of class from him and his agent saying that he would have come but, in the end, Milan proved to be place where he felt it was right – whether it was financial or not.
“At the end of the day, really, they made him an offer he couldn’t refuse.”
So did Spurs, but to Jonathan Blondel and Rohan Ricketts instead.
Paulo Dybala
Actually, a better place to end might be with the labyrinthine ridiculousness of red tape Spurs found Dybala covered in when they tried to build on reaching the Champions League final in 2019.
Are image rights really worth obsessing over when you could play with Serge Aurier and Steven Bergwijn?
