Daniel Levy’s 24 years at Tottenham saw countless near misses in the transfer market. Let’s have a look at the deals the former Spurs chairman almost pulled off that would have changed the course of the club’s history.
Daniel Levy stepped down as chairman of Tottenham Hotspur last week after serving almost two and a half decades, making him the longest-serving chairman in Premier League history.
It was widely reported that Levy was actually pushed out of Spurs. Frustration was mounting among fans and rival clubs over the way Levy conducted business at Tottenham, particularly in the transfer market, where negotiations dragged on and deals often collapsed.
However, even Levy’s harshest critics will agree that there were countless “what if” moments. Big names came close, talks were held, fees discussed, but the deals never happened.
Here are the 10 biggest deals Daniel Levy missed out on at Tottenham
According to The Athletic, Spurs had Van Dijk on their radar in the summer of 2015 when he was still at Celtic. But he was only considered as Plan B. Levy’s priority was Toby Alderweireld, and once that deal was sealed, the club didn’t push for Van Dijk. Southampton took their chance instead, and a few years later, Liverpool turned him into a £75 million legend.
Former Spurs scout David Webb revealed that Tottenham came very close to signing Sadio Mane from Southampton. Paul Mitchell, then Tottenham’s head of recruitment, who had also worked with him at St Mary’s, pushed hard, and Mane even visited Spurs’ training ground in 2016. A fee of around £34 million was discussed, but Levy refused to break the club’s strict wage structure for him. Liverpool, offering £90,000 per week, secured him while Spurs ended up paying £30 million for Moussa Sissoko instead.
In August 2019, Spurs agreed a fee of around £65 million with Juventus for Paulo Dybala. He was open to working under Mauricio Pochettino, but the deal collapsed on deadline day. Complications over the player’s image rights, worth around £15 million, became the stumbling block. The image rights would have needed to be bought out as part of the deal, but Levy’s reluctance to pay the full sum meant the move collapsed. However, Dybala himself later admitted he wanted to stay in Turin.
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Levy’s name circled around Samuel Eto’o on three separate occasions. In 2002, Spurs were linked with the 21-year-old Mallorca striker but, like many clubs, hesitated. In 2008, Levy made contact with Barcelona but pulled out because of the €35 million asking price. By 2012, Spurs even offered £24 million and wages of £107,000 per week, with Levy willing to fly to Barcelona himself to close the deal, but Eto’o publicly dismissed the idea, saying Spurs were “mid-table” and he wanted a bigger stage.
This one still stings. In 2013, Spurs had Willian at Hotspur Way, medical completed, and a fee agreed with Anzhi Makhachkala for £30 million. Levy thought it was sealed, but Chelsea and Roman Abramovich swooped in with a last-minute call to Anzhi’s owner. For a slightly bigger fee, Willian switched sides and signed for the Blues. Levy was said to be “incandescent” and believed that Chelsea did not truly want Willian. To make matters worse, Jose Mourinho openly mocked Spurs, saying they should have done the medical in secret.
In 2014, Spurs lodged a €23 million bid for Antoine Griezmann, then at Real Sociedad. Levy led the negotiations but refused to meet the €30 million release clause. Sociedad stood firm, and Griezmann went to Atletico Madrid instead. Griezmann’s former agent confirmed Tottenham’s interest, making this one of the clearest cases of Levy’s frugality costing the club a future superstar.
In his book A Man Walks On To a Pitch, Harry Redknapp revealed that he visited Patrick Vieira at his house in Hampstead in 2009 to discuss a potential move to Spurs from Inter Milan. Despite his legendary Arsenal past, Vieira showed no fear about it. Redknapp later spoke with Daniel Levy, who raised concerns about the likely hostile reaction from supporters. Ultimately, the former Arsenal captain decided to remain in Italy before joining Manchester City a few months later.
Harry Redknapp admitted that Spurs had the chance to sign Luis Suarez before he left Ajax in 2011. Ruud Gullit strongly recommended him, and Redknapp pushed for the deal, but Tottenham’s scouts reported that Suarez mostly played wide rather than as a central striker, which is what Spurs needed at the time.
Levy hesitated, and by the time the club revisited the move, Ajax had raised the price. Liverpool eventually signed him for £22.8 million, and Redknapp described missing out on him as one of his ‘biggest regrets in life’.
In 2012, Harry Redknapp had identified Eden Hazard at Lille and was convinced he was the one player Spurs needed. After Joe Cole told him just how good the Belgian was, Redknapp even travelled to France, met Hazard and his agent, and the winger was keen on a move to North London. The fee was £16 million, but Levy refused to pay it. Chelsea did, and Hazard went on to become one of the best players in the Premier League.
The biggest of them all. Former Spurs player and scout Ronny Rosenthal recommended Cristiano Ronaldo to Levy and Co in 2002, when the teenager was just breaking through at Sporting Lisbon. Spurs, along with Arsenal, passed. A year later, Ronaldo impressed in a friendly against Manchester United, and Sir Alex Ferguson snapped him up for £12 million.
Nearly two decades later, in 2022, Ronaldo was unsettled at United. Reports claimed Levy and Antonio Conte briefly considered a move, given Fabio Paratici’s links to Juventus, but dismissed it quickly. Twice Spurs had the chance; first when he was unknown, then when he was a global icon. Both times, Levy didn’t pull the trigger.
Honourable mentions and what’s next for Tottenham
There are others worth noting. Rivaldo was close to Spurs in 2002 but Levy refused to meet his wage demands.
Real Madrid forward Raul was also discussed at Tottenham, but managerial changes at Spurs halted talks. Kylian Mbappe, meanwhile, was watched closely by Spurs after impressing against them in a Europa League fixture in 2015 whilst at Monaco, but he preferred to stay in France to develop.
