Spurs have a long history of failing to get deals over the line in the transfer market, with the circumstances usually unique
When it comes to defining 'Spursy', the footballing community should hold itself to a higher standard. Any team can lose after going two goals up, any side can snatch defeat from the jaws of victory, and ultimately, every fanbase thinks that the universe has it in for them. That's just how sport works.
For Tottenham, however, there is more of a unique history of shenanigans which range from painful, like Sol Campbell's move across north London to Arsenal for free after he said he would stay, to ironic, such as their director of football Fabio Paratici receiving a global footballing ban while running their transfer operations.
Even on the recruitment level, most clubs find themselves stuck in what feels like an endless loop of misadventure – Manchester United supporters were well versed with Nico Gaitan from about 2012 to 2015 without him ever playing for them, for example. But again, the case of Spurs feels strangely unique, with some of their failed deals owing to the most incredible circumstances.
Here are 10 of the most incredulous tales they have found themselves in:
Follow GOAL on WhatsApp! 🟢📱Getty Images SportGibbs-White's release clause
We'll start with the most recent grievance, and it's already among the most major in Spurs' history. On July 10, news broke that Tottenham had triggered the £60 million ($80.5m) release clause in the contract of Nottingham Forest midfielder Morgan Gibbs-White, and he would undertake a medical the next day. Reports of Spurs' interest only came out a couple of hours before this, and shortly after they had completed the £55m ($74m) signing of Mohammed Kudus, lifting the general mood around the club after a slow start to the summer window.
What happened next will live long in the memory. Instead of Gibbs-White undergoing a medical, Forest threatened Spurs with legal action and later lodged a complaint to the Premier League over their approach, believing the release clause was secretive and there was a breach of confidentiality. It did initially seem as though this would only delay the deal, and various transfer window insiders claimed that ultimately the player would end up in north London.
There was a fortnight of relative silence. Nobody outside of the two clubs involved seemed to know for sure what was happening. There were reports that Manchester City could reignite their historic interest and Forest would prefer to sell to them given their newfound vendetta against Tottenham, but that didn't come to pass.
Late on July 26, Forest announced that Gibbs-White had signed a 'record' three-year contract and would be staying. He and the club's social media accounts repeatedly thanked owner Evangelos Marinakis for making it happen, in what was among the strangest uses of the internet since it became a worldwide public forum. But whatever you make of how weird that was, Spurs had been rumbled somehow.
AdvertisementGetty ImagesEze hijacked
Eberechi Eze is, by all accounts, one of football’s good guys. He even really wanted to sign for Tottenham despite his boyhood allegiances to the team from down the road, Arsenal. It’s part of the reason why it will be so painful for Spurs fans that they will have to hate him for the rest of their lives.
By the morning of August 20, 2025, Tottenham, Crystal Palace and Eze himself had a broad agreement over a transfer. Following the first leg of the Eagles’ Conference League play-off against Norwegian side Fredrikstad, the door would be opened for a move to go through and be signed off by the top brass at Selhurst Park.
Around the same time, Arsenal were lurking. They had just learned Kai Havertz would spend an unspecified amount of time sidelined with another knee injury and needed reinforcement in the final third. They had considered Eze earlier in the window, but decided against advancing that interest. This is what allowed Spurs, themselves looking to replace a maverick with a knee problem in the ACL-ridden James Maddison, a window of opportunity. It slammed shut right on their fingertips.
Arsenal dallied no longer. They went to Palace and told them they would match whatever Spurs were willing to pay, perhaps even add a little more on top. For a week, Eze was a Tottenham player in waiting, and they failed to get him over the line. A month on from the Gibbs-White nonsense, the club had outdone themselves again.
Getty Images SportDybala's image rights
Tottenham's 2019 summer window, which immediately followed their first and only appearance in a Champions League final, saw them smash their transfer record to sign Tanguy Ndombele for an initial £55m. And yet they nearly spent an even greater sum on a vastly more proven player.
Mauricio Pochettino, not knowing he was heading into his final few months in the manager's job, wanted to refresh his attack, and set his sights high with a top target of Paulo Dybala. Then of Juventus, the Argentine forward was open to joining Spurs, even though he was happy in Turin and felt he was being forced out by the club for no good reason.
The problem for Tottenham was when they chose to conduct their business. Chairman Daniel Levy is known for preferring to move late in the window in order to get better value on deals, and this wasn't the first time that he gave himself too much to do in a short space of time.
For 2018 and 2019, the Premier League experimented with closing the transfer window before the opening day of the season, mainly to appease clubs who said leaving it open for the entirety of August left them vulnerable and they should be able to begin a campaign with a settled squad. The rest of Europe refused to follow in their lead, and so English sides shot themselves in the foot despite their best of intentions.
Spurs stepped up their interest in Dybala in the final week of the Premier League's window and came to a broad £70m agreement with about 48 hours before the deadline, but they were yet to solve a two-word issue that has become folklore for the wrong reasons – . When he was younger, Dybala sold his image rights to a third-party marketing company known as Star Group, and in order for Tottenham to register him, they would need to purchase those as well. The legal matter became too complex with too little time to navigate and the move was called off.
In 2021, Dybala settled this dispute with Star Group for little over £30m, showing just how much more Spurs would have had to pay to get the deal done.
AFPWillian's medical
A story as famous on these shores as the player himself. Amid their £100m splurge on players to fill the hole about to be left by Gareth Bale, Tottenham targeted Anzhi Makhachkala winger Willian and agreed a £30m fee. What's more, he even underwent a medical and a deal seemed to be complete, when all of a sudden Chelsea entered the race. The player's head was turned and he left Spurs in the lurch to join their fierce London rivals instead.
Willian later revealed that he only found out about Chelsea's bid as he arrived at Tottenham's training ground, where he was told by his agent to get back in the van he arrived in so they could set forth for the Blues' Cobham base instead. Though sometimes a frustrating player, Willian was adored by the Chelsea faithful for his work ethic, contributions in winning several titles, and the chant they were able to sing on the terraces:
