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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.

Richarlison has been speaking to the Brazilian media about the start he has had to the season and shed light on what Thomas Frank did to get the best out of him at Tottenham.

Dominic Solanke’s injury problems have offered Richarlison an opportunity to have a run in the Spurs side so far this season, and he has grabbed it with both hands.

Despite the constant speculation over his future during the summer, the 28-year-old has insisted that he never considered leaving Hotspur Way this summer.

In fact, Richarlison informed Thomas Frank he wanted to stay in the pair’s first conversation after the Danish coach walked through the door at Tottenham in the summer.

Richarlison admits he is following Thomas Frank’s plan closely at Tottenham

The Brazil international’s constant injury woes have meant that he has not been able to showcase his best in a Spurs shirt over the last three years.

The striker revealed that Frank and his staff have prepared a specific fitness plan for him through pre-season, which he is following to a tee.

Speaking after Brazil’s 3-0 win over Chile, the Tottenham man told Itatiaia Esporte: “I had a good pre-season, worked hard, and the new Tottenham coach [Thomas Frank] made a plan for me.

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“I managed to follow that plan closely and everything went well. So I started this season well, and I hope to keep it that way to earn my spot.”

Richarlison admits he faces a big Brazil challenge

Richarlison came on as a 78th-minute substitute against Chile, with Chelsea’s Joao Pedro getting the nod to start over him as the centre-forward.

The Tottenham man was the Selecao’s first-choice number nine heading into the last World Cup, but he admitted that he faces a sterner challenge forcing himself into Carlo Ancelotti’s starting eleven, given the competition he now faces.

When asked about becoming Brazil’s first-choice centre-forward in the United States next summer, Richarlison said: “I think the pressure is bigger, but what matters is that I keep working hard. I want to win that confidence back. I had injuries and personal problems before, but that is resolved now.”

Tottenham Hotspur continue to eye a move for a Netherlands international in the January window, but they will face competition for the player from Newcastle United and Liverpool.

It has been reported over recent days that, following Daniel Levy’s exit, we are expected to see a change in Tottenham’s transfer policy.

Spurs are expected to shop for ‘elite’ players in January in order to compete for major honours, with a centre-back and a new attacking player at the top of the club’s wishlist.

Jan Paul van Hecke was on Tottenham’s radar in the summer, and the Lilywhites are continuing to keep their eye on the Brighton man, but their pursuit of the 25-year-old has just got a lot harder.

Liverpool enter race with Tottenham to sign Jan Paul van Hecke

GiveMeSport have claimed that Tottenham Hotspur and Newcastle United are continuing to keep tabs on the Dutchman ahead of the January window.

However, those two clubs have now been joined in the race for the Seagulls star by Liverpool, who have identified van Hecke as a potential alternative to Marc Guehi, who they failed to sign on deadline day.

The Reds have now expressed an interest in luring the Dutch defender away from the Amex Stadium when the transfer window reopens, while Newcastle also remain keen on bolstering their defensive options.

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Van Hecke’s is waiting for a transfer approach

GiveMeSport say that the centre-back had a price tag in the region of £44m during the summer transfer window, and his current employers were determined to fight off suitors.

However, Brighton’s efforts to tie Van Hecke to a new contract have not proven successful, with the player aware that he is on the radar of top clubs and waiting to see if they substantiate the interest.

Tottenham’s Pedro Porro says it is not uncommon for professional footballers to not watch any football in their time off, but he confessed that he is very different and cannot get enough of the game.

Football fans often assume that professionals are obsessed with the game as much as they are, but that is not necessarily true.

While the players who get to the highest level are often committed to becoming the best player they can be, not all of them are necessarily passionate about watching the sport.

Former Tottenham left-back Benoit Assou-Ekotto even admitted that he only plays football for money and that he does not enjoy playing the game professionally, but one current Spurs full-back is the polar opposite of the Cameroonian.

Porro has confessed that he is a football fanatic who cannot get enough of the game, tending to watch whatever is on.

He revealed that while many of his fellow professionals like to switch off from the game in their off time, he prefers watching all kinds of matches.

When asked how the La Liga is perceived in England, the Tottenham man told Thursday’s edition of ABC (as relayed by Sport Witness): “I haven’t spoken to anyone about the Spanish league, I won’t lie. But I’m a fan of football; I follow the Spanish League. I’m a player who likes to watch all kinds of games.

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When asked whether or not it’s common among professional players to watch football, Porro responded: “I think it’s the other way around. There are people who play but don’t really like watching football.

“I love it. If I can have it 24 hours a day… I’m a football fanatic. There are players who do like watching football and others who say, ‘I’ve got enough with what I have.’ In my case, it’s true that I’m a big football fan.”

Porro admits he takes learnings from other players

The Tottenham Hotspur right-back revealed that he not only re-watches the matches he plays in but also tries to take pointers from other teams and players.

Porro insisted that the things he picks up from watching other teams have helped him gain a better understanding of various situations on the pitch and become a better player.

He added: “I always watch it, not just the matches I play in. I like to take things away from it, concepts, because they can often be useful when you’re in difficult situations. Like what happened to me with Spain.

“I reviewed it, not the match itself, but the concept that I could improve on from there. That’s why I like to review all kinds of football, because at the end of the day, it can help you later on.”

Tottenham Hotspur are plotting a move to re-sign one of their academy graduates, who has found game time hard to come by at the start of the new Premier League season.

Spurs had a solid transfer window, bulking up their squad with seven signings ahead of their return to the Champions League.

However, Tottenham’s lack of homegrown and club-trained players cost them dearly, with Thomas Frank having to leave out six players from the Champions League squad for the League Phase.

That is an issue the Lilywhites will have to solve, and they are now eyeing an interesting solution, with a young defender who left the club back in 2021 on their radar.

Tottenham are considering re-signing Dennis Cirkin

TBR Football have now claimed that Thomas Frank is considering bringing Dennis Cirkin back to Tottenham Hotspur Stadium.

The left-back was rated highly while coming through the ranks at Spurs, but he left in 2021 for the Stadium of Light without making a senior appearance for the North London club.

Cirkin has developed impressively over the last few years and has been a key part of the Black Cats’ journey from League One to the Premier League.

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With Spurs needing cover at full-back, the report says that there is a ‘real chance’ that they will make a move for the 23-year-old.

Cirkin is frustrated at Sunderland as Spurs eye opportunity

TBR Football say that the Republic of Ireland international is frustrated at the North East as he has fallen down the pecking order after the arrival of Reinildo from Atletico Madrid in the summer.

Additionally, the former Tottenham Hotspur man will have just six months left on his contract in January, which means that it will be Sunderland’s final opportunity to get a fee for him.

Spurs may thus be eyeing a cut-price deal for Cirkin, but it remains to be seen if the youngster would be too enthusiastic at the prospect of swapping one bench for another, or if he will prefer moving to a club which can guarantee him game time.

A player who arrived through the door at Tottenham late in the transfer window was one of Atletico Madrid’s top targets this summer, according to a new report from Spain.

Among the seven signings Tottenham made this summer, the Simons deal is the one that has got Spurs fans most excited.

It is easy to understand why, with the 22-year-old arriving at Spurs on the back of two excellent years for club and country, and appearing to be on the cusp of becoming a world-class player.

Johan Lange has said that Simons’ hunger and desire to improve were evident during the club’s conversations with the player, which is something that will be music to the ears of Tottenham supporters.

Tottenham beat Atletico Madrid to the signing of Xavi Simons

According to a report in Marca, Tottenham got the better of Atletico Madrid in the race to land the former Leipzig man, who was on the La Liga club’s radar.

The report says that Diego Simone’s side were looking to add a new attacking midfielder to their squad in the summer.

While they eventually settled for Nico Gonzalez, it is alleged that Simons was seen as the ‘perfect choice’ by Atletico.

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However, the report explains that the Spanish side could not afford to match Tottenham’s offer for the Netherlands international.

Tottenham also beat their London rivals to Simons

All through the summer, it was one of Tottenham’s London rivals who were installed as the favourites to land the 22-year-old, with reports indicating that Chelsea had even agreed personal terms with Simons.

However, Spurs managed to hijack Chelsea’s move for Simons in the final days of the transfer window, with the Blues not even submitting an offer for the player at the end.

Tottenham Hotspur reportedly failed with a late move for one of Ligue 1’s most exciting wingers, and the Lilywhites are expected to try again in January.

It came as a surprise to some Spurs fans when Tottenham signed Randal Kolo Muani on deadline day instead of a winger.

We know that Spurs were scouring Europe for a winger in the final days of the transfer window, and one would assume that the position will become a priority for Thomas Frank’s men in January.

It has now emerged that the Lilywhites failed with a last-ditch move to sign a Belgian international winger in the final days of the window, but they could try again in January.

Tottenham remain interested in Lyon star Malick Fofana

Malick Fofana’s stock has grown considerably over the last 12 months after the winger scored 11 goals and provided six assists last term.

It is perhaps a surprise that he ended up staying at Lyon, but it has now been revealed by CaughtOffside that Tottenham tried to sign the 20-year-old in the final days of the transfer window.

The outlet says that the deal for the Belgian fell through as Lyon did not have enough time to secure a replacement.

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However, Spurs are continuing to show interest in Fofana, with industry sources expecting the Premier League side to try again for the winger in January.

Tottenham will face competition for Malick Fofana

CaughOffside say that while Tottenham Hotspur are the ones showing the strongest interest in Fofana at the moment, they are not the only circling over the player.

It is revealed that Liverpool are keeping a close eye on the youngster’s situation ahead of the January window.

Additionally, Serie A giants, Inter Milan, are alleged to be ‘really keen’ on taking Fofana to the San Siro.

Tottenham Hotspur could rekindle their interest in one of the most sought-after Premier League stars after failing to get a deal over the line during the summer transfer window.

We have heard over recent days that the exit of Daniel Levy could usher in a new era at Tottenham, who want to sign elite players to give themselves a chance of competing for major honours.

It was reported during the summer that Tottenham wanted to test Villa’s resolve to hold onto Morgan Rogers, given the Midlands club’s financial issues.

However, in the end, Unai Emery’s men made it clear to the Lilywhites that their star man is not for sale. It turns out that the North London club have not given up their dreams of signing the England international just yet.

Morgan Rogers remains at the top of Tottenham’s wishlist

TEAMtalk now claim that Spurs could emerge as more serious contenders for Rogers when the transfer window reopens in the summer.

The outlet says that Tottenham made a late approach for Rogers but found that Villa were not willing to come to the negotiating table.

However, the Lilywhites are now ready to embark on a new era following Levy’s exit and are eyeing more ambitious and progressive investment in the transfer market.

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Rogers remains at the top of Spurs’ wishlist, and the club could swoop for the former Middlesbrough man to signal their ambition.

Tottenham are not put off by Aston Villa’s huge valuation of Rogers

TEAMtalk say that following an approach from Tottenham Hotspur, Villa are expected to slap a valuation of around £100m on their star attacker.

While that figure was considered out of Spurs’ reach during Levy’s reign, there is now a growing belief that the club could stretch themselves financially to bring Rogers through the door.

Tottenham will soon come face-to-face with their former manager, Ange Postecoglou, as the Australian makes a swift return to the Premier League dugout with Nottingham Forest.

Ange Postecoglou has made a rather quick return to management, just months after being dismissed from Tottenham Hotspur.

The 60-year-old has now taken up the reins at Nottingham Forest, following the sacking of former Spurs boss Nuno Espirito Santo.

Postecoglou had been linked with a number of roles across the Premier League and Europe, with Turkish side Fenerbahce also registering strong interest in the Australian.

When Ange Postecoglou is set to face Tottenham in Premier League return

With the former Spurs boss now back in the Premier League, Tottenham supporters will already be keeping an eye on when he will go head-to-head with Thomas Frank at Spurs.

According to the fixture schedule, Postecoglou’s first meeting with Tottenham is set for 13 December 2025 at the City Ground, giving him time to settle into his new role before facing his former club.

The return fixture is pencilled in for 21 March 2026, although as always, broadcast adjustments could still alter those dates.

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Postecoglou set for Europa League title defence with Nottingham Forest

Postecoglou has plenty to look forward to as Nottingham Forest manager, beginning with his first game this weekend against Arsenal, an opponent he knows very well.

Tottenham fans will no doubt be hoping that he can snatch a victory against their bitter rivals, as the Australian looks to mark his Forest tenure with an early statement.

Tottenham’s chief executive officer, Vinai Venkatesham, who has now become the main man at the North London club after Daniel Levy’s departure, has shed light on his working philosophy.

According to reports, it was Levy who persuaded Venkatesham to join Tottenham as the CEO, but in a surprise move, the former Spurs supremo has now been ousted by the Lewis family.

Venkatesham has already got stuck in and made some important decisions in his first few months at the club. In fact, it was reportedly the Spurs CEO who persuaded Cristian Romero to sign a new contract.

However, the former Arsenal chief has now seen his role change, and he has underlined how he will proceed as the man calling the shots at Spurs.

Vinai Venkatesham explains his working philosophy

Some sources have claimed that the changes at the boardroom level, including the hiring of Venkatesham, were done with Levy’s exit in mind by the Lewis family.

That suggests that the Lewis family very much saw the 42-year-old as someone who could take charge of the club, but the Spurs chief has now suggested that even though he might be the face of the club’s decisions, it will be a team effort.

When asked about the changes to his role, Venkatesham told Tottenham’s official website: “Well, I think it’s fair to say it’s been a very, very busy three months.

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“There’s not been much in the way of weekends or evenings. There’s not been much in the way of sleep. So, it’s been a very busy start, but everybody’s been really welcoming inside and outside the Club – very warm, very welcoming – so, I feel really, really settled in.

“I’m enjoying it, and I’m looking forward to the challenge ahead, but the really important thing to be clear on is this is not just about me, and it’s certainly not all about me. Everything that we achieve at the Club will be part of a team, and I mean that.

“So, naturally, I guess, as Chief Executive, my name ends up in the media, and I end up sitting here and doing an interview with you, but we’ve got 800 people at the Club, and we need everybody in the Club pulling together to drive us forward. This is certainly not all about one person or a small group of people.

Venkatesham says it will be business as usual at Spurs

Despite the huge change at the top, the Spurs CEO insisted that there will be continuity at the North London club in terms of the technical staff.

He reiterated that success on the pitch remains the club’s focus and that the staff will be backed to deliver trophies to N17.

When asked what comes next for Tottenham, Venkatesham said: “As I said at the start, it is business as usual in many ways. When I joined, I talked about wanting to do three things. The first is doing everything I can to support our excellent technical teams on the ground, both on the men’s side and the women’s side, to give us the best chance to be successful on the pitch.

“That continues to be a focus. I said my second focus was going to be around our people at the Football Club, making sure that we’re doing everything we can to empower them to be at their best, to drive the Club forward, and have the best people with the best culture to deliver against our ambitions.

“And the third one was our relationship with our supporters – make sure that they’re right behind us, make sure that they understand what we’re trying to do, communicate better with our supporters and ultimately, make them proud of what their Football Club is trying to do and what our Football Club over time will deliver.”