Daniel Levy made a few high-profile mistakes during his time as Tottenham chairman, but one is now seriously coming back to haunt him.
Daniel Levy leaves behind mixed Tottenham legacy
Levy's resignation after 24 years as head of the Lilywhites boardroom sent shockwaves throughout the world of football.
He was regularly the target of criticism and even protests towards the end of his tenure, following a perceived lack of on-field ambition when compared to Spurs' big-spending Premier League rivals.
Levy oversaw just two major trophy wins — the Carling Cup in 2008 and Europa League this year — but helped to transform Tottenham into a financial powerhouse off the pitch.
The 63-year-old helped to instigate Spurs' transformative move to their brand-new state-of-the-art stadium and training facilities, which have made them one of the highest-potential clubs in Europe for success.
Nearly three weeks ago, the news of his departure is still attracting plenty of debate, following reports that Levy was pushed to resign from Tottenham by the Lewis family and found out just hours before it was made official (The Times).
The chief made some pretty questionable calls as chair, not least the appointments of highly unsuitable managers which turned out to be disasters.
In terms of the transfer market, while there are plenty of success stories, one decision that's now coming back to bite him is the refusal to strike a deal for PSG superstar Ousmane Dembele.
The Frenchman has resurrected his once-faltering career under Luis Enrique at the Parc des Princes, and fresh off the back of a stellar 24/25, he was crowned this year's Ballon d'Or winner on Monday evening.
Dembele's staggering 35 goals and 16 assists in all competitions last season, including an heroic Champions League final display against Inter Milan, gifted PSG a long-awaited treble whilst etching his name into the club's history.
His winner away to Arsenal in the Champions League semi-finals also turned out to be crucial, with the £317,000-per-week attacker starring in multiple positions as both a centre-foward and wide player across 24/25.
Tottenham refused chance to sign Ousmane Dembélé in 2022
Looking back to three years ago, it is now very interesting to note that Tottenham were actually offered the chance to sign Dembele
That is according to reliable journalist Alasdair Gold, who reported at the time that it was a 'polite no' to the opportunity of negotiating a deal for this year's European player of the year.
This blunt response to Barcelona's offering of Dembélé is made all the more humbling for Levy, considering how the 28-year-old has set France alight since his move to PSG just one year after Tottenham were approached.
The ex-Barca flop's rise back to the pinnacle of footballing stardom has been a wonder to behold after injuries largely dampened his time at the Camp Nou, with Enrique explaining that Dembele's "impeccable" attitude was perhaps a key factor.
"He is a player full of confidence," Enrique told reporters in February.
"Back when I played PlayStation as a kid, he was the kind of player you'd choose when you needed someone to change the game.
"He was already good last season but in 2025 he is even better. You can see his teammates looking for him and finding him. He has an impeccable attitude."
Now, it is highly unlikely Spurs will get such a chance to sign him again, and it further highlights just how quickly things can change in football.