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The familiar story of a Tottenham transfer saga: From Damião to Tonali

The trials and tribulations of a typical Tottenham Hotspur transfer window. Sandro Tonali is the latest chapter in a story that spans generations. With some new main characters, could we finally be in for a happy ending?
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FBL-ENG-PR-NEWCASTLE-TOTTENHAM | PAUL ELLIS/GettyImages

Last night, transfer aficionado Fabrizio Romano broke the news that Tottenham Hotspur could be a serious destination for Newcastle midfielder Sandro Tonali as Roberto De Zerbi looks to bolster his options ahead of the 2026/27 season, sending the virtual terraces into a frenzy.

While the news is sure to be welcomed as a central midfielder of Tonali's quality is a vital need this summer, if the history of the Tottenham has taught us anything it's that we must tread cautiously when celebrating rumours as if they are done deals.

It seems as though Tottenham Hotspur has historically been a fertile breeding ground for transfer heartache. Losing club captains to local rivals. Missing out on long term targets to said rivals. Settling for unproven talent and eventually having to start the whole transfer process all over again.

Just last summer, Tottenham became the only club to ever get Romano's famed “Here We Go” and not see the deal over the line when Morgan Gibbs-White’s transfer from Nottingham Forest collapsed. To add insult to injury, their next target, Eberechi Eze, was as good as done when their North London neighbours swooped in on the eleventh hour and took the England attacker from under their nose.

Gibbs-White and Eze were just the latest chapter in a history of heartbreak at Hotspur Way over the years.

Dybala to Damião: Tottenham's endless summer torture

There is a plethora of stories to add to last summer's collapsed deals and last minute u-turns to add fuel to the 'Spursy' signings rhetoric. Following the club's sole Champions League final appearance in 2019, headcoach Mauricio Pochettino was desperate to build on his side's European momentum and add talent that would help them to continue to challenge at the top table.

The Argentine earmarked his compatriot, Juventus attacker Paulo Dybala, with the player said to be keen on the move to North London from Turin. Spurs waited until the final days of the transfer window to agree in principle a £70 million move, only for the deal to collapse due to complications with the player's image rights which were owned by a third party.

Another infamous fable in the folklore of Tottenham's done deals comes in the form of Leandro Damião, the Brazilian attacker who was consistently linked with a move to Tottenham between 2011 and 2013. A move never materialised, due to the trademark Tottenham lowball.

In a 2019 interview with the Athletic, Internacional president at the time Giovanni Luigi confirmed that they opened talks in 2011 but Daniel Levy's offer of around €8 million fell well below their asking price. On another occasion in 2013, Luigi noted how Tottenham opened initial negotiations but never made a formal bid.

"“Tottenham wanted to discuss it in person. I said I was open to that, but it didn’t happen. At no moment did we receive an offer in writing for him. Tottenham never put anything down on paper.""
Giovanni Luigi

And so, the story of Leandro Damião gradually transitioned from transfer bomba to mythical tale over the course of three years.

The Tottenham Transfer Way

The laughable bid for Jack Grealish. Willian's medical. Rivaldo's letter. David Raya. Eden Hazard. Saido Berahino. Joao Moutinho. The tales of the trials and tribulations of Tottenham transfer news read more like a tragicomedy series. They all, however, follow similar narrative arcs.

A journalist drops an exclusive. Fans rush to find compilations and picture them in lilywhite, drawing up tactics with enthusiasm that borders delusion. He's coming, he's not. He's coming. He's...not. The deal collapses. Spurs have moved too late. The player signs a new contract, or signs elsewhere. It turns out the player was never actually available, or that Tottenham never actually made a bid at all.

However, make no mistake. This is not a tale of Tottenham fans' delusion. It's a tale of a group of loyal supporters who long for their beloved club to make that next step, after years of knocking on the door and getting sent a few houses down to go knocking again.

Tonali would indeed be a statement signing, and one that would make the signings of Robertson and Sensesi look even more shrewd. With new personnel in the boardroom this time around, it's time for the club's hierarchy to back up their promises of club transformation and match the optimism and ambition that their fans have shown for some time now, so we can start writing a new story for Tottenham Hotspur together with many happy endings.

Given the history of recurring marquee transfer mishaps, however, maybe let's hold our respective breaths and save the 'we're winning the lot' chat until we see a 'here you are' rather than a 'here we go.'

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