Ousmane Dembele’s Ballon D’Or win on Monday night has brought up yet more bitter memories for Tottenham.
The PSG winger was crowned as the world’s best footballer at the 2025 ceremony in Paris, after an electric season that saw him named as both the Ligue 1 and Champions League Player of the Year.
Ex-Tottenham hero Harry Kane was also a nominee for the award, but ultimately finished in a lowly 13th place.
The Lilywhites will have been watching on with envy on Monday, as yet more frustration is likely to mount towards Daniel Levy.
Tottenham almost signed Ousmane Dembele twice
Tottenham had the opportunity to sign Dembele back in 2016, when they held discussions about him during his early rise through the ranks at Stade Rennes.
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Borussia Dortmund won the race to secure his signature on that occasion, and later secured an incredible deal that potentially rose as high as £135.5million, as they sold him to Barcelona after just one season.
However, it wasn’t plain sailing for the Frenchman at the Camp Nou, as injuries heavily disrupted his career.
The N17 outfit held a “serious” interest in Dembele, according to journalist Fernando Polo via his X account, but were ultimately unable to get a deal done.
That was a recurring theme of Levy’s reign as executive chairman, and this was just one of many instances where the Spurs chief was found wanting when it came to securing high-profile transfers.
The 63-year-old made a major blunder by not making a move for the wideman, and everyone at the Tottenham Hotspur Stadium will now be wondering what could have been.
Spurs have to change after Daniel Levy exit
Levy did many positive things at Tottenham on the business side of the club, but his work in a footballing sense often left a lot to be desired.
It became a common theme over the years for the North Londoners to miss out on key transfer targets, and that is something that simply must change if they are to improve as a club following his exit.
The early signs suggest that Levy’s exit will be used as a force for good in N17, but only time will tell whether it proves to be a positive event or not for the club.