Counting down Daniel Levy's top 10 Tottenham transfers, starting with Kyle Walker - Opinion

Let’s take a look at Daniel Levy’s top 10 signings for Tottenham, including value buys and iconic game-changers in North London.

Daniel Levy officially stepped down as executive chairman of Tottenham Hotspur on Thursday, bringing to an end more than 24 years in charge of the club. However, he still retains a 29 per cent stake in ENIC, meaning there is no change to the ownership or shareholder structure.

The move felt inevitable after a series of reshuffles in recent months, including the arrival of Vinai Venkatesham as CEO and multiple fan protests. In the wake of Levy’s exit, Peter Charrington has joined the board and will take on the newly created role of non-executive chairman.

Levy may never have been a fan favourite, but even his harshest critics would admit he pulled off some masterstrokes in the transfer market. Here are the ten best signings of his reign.

Daniel Levy’s top ten Tottenham transfers across 24 years

10. Tottenham sign Kyle Walker from Sheffield United

Kyle Walker arrived as part of a combined deal with Kyle Naughton from Sheffield United for about £9 million in 2009. Walker spent loan spells at Aston Villa and QPR before establishing himself at Spurs as one of the best right-backs in the world. In 2017, he left for Manchester City for a fee reported at £45 million, rising to £50 million with add-ons.

9. Aaron Lennon cost Tottenham just £1m

Aaron Lennon was signed from a desperate Leeds United in 2005 for just £1 million as Leeds struggled with finances. Daniel Levy being Daniel Levy, had to take advantage of the situation. Lennon went on to give Spurs a decade of service, making 327 appearances and becoming a regular England international starter. He later moved to Everton in 2015 for £4.5m. Not the biggest profit, but huge impact for very little outlay.

8. Dimitar Berbatov was a successful purchase and sale

Dimitar Berbatov admitted he had never even heard of Tottenham before signing from Bayer Leverkusen for £10.9m in 2006 after Spurs beat off interest from Manchester United to land him. The Bulgarian striker was sheer class, scoring 34 goals in two seasons and lighting up White Hart Lane. Levy, of course, dragged his departure to deadline day in 2008, eventually selling him to Manchester United for £30.75m.

7. Mousa Dembele is a Tottenham icon

Sometimes transfers aren’t about profit. Mousa Dembele arrived from Fulham in 2012 for £15m, just a day after Luka Modric’s sale to Real Madrid. Dembele was unplayable on his day, with Harry Kane, Jan Vertonghen and even Kevin De Bruyne calling him the best they had ever played with. He went six consecutive months without being dispossessed once in the Premier League. After 250 appearances, he left for Chinese club Guangzhou City in 2019 for £11m.

6. Jan Vertonghen was an absolute bargain for Spurs

Jan Vertonghen joined Spurs in 2012 from Ajax for around €12m after publicly stating he wanted to play at White Hart Lane, despite interest from rivals Arsenal. He became a mainstay of the Spurs’ defence for eight seasons, a leader who was central to the club’s rise into the Champions League era under Mauricio Pochettino. His career dipped after a serious concussion in the 2019 semi-final against Ajax, and he left on a free to Benfica in 2020.

5. Tottenham even made a profit on Christian Eriksen

Tottenham signed Christian Eriksen from Ajax in the summer of 2013 for just £11 million, one of the “Magnificent Seven” signings funded by Gareth Bale’s departure to Real Madrid. Levy moved quickly as Eriksen had just one year left on his contract, and without doubt, he proved to be the most successful of the seven. He cost the least but delivered the most, making over 300 appearances for Spurs and becoming the top assister in the club’s history.

Eriksen eventually forced a move in January 2020 to Serie A side Inter Milan for around €27 million, despite Levy’s wish to keep him, at a time when his market value was closer to €90 million.

4. Hugo Lloris was at Spurs for nearly a decade

Hugo Lloris was secured on 31 August 2012 in what was a classic Levy deadline day move. The deal was reported as €10 million plus €5 million in add-ons, with Lyon also set to receive a 20 per cent sell-on clause. Arsenal’s Arsene Wenger had pushed hard for him, but Levy personally wanted the Frenchman, and even Lloris admitted in his autobiography that he was the “chairman’s signing.” Lyon’s president later blasted Levy for being ‘ridiculously hard’ to deal with.

Lloris went on to make 447 appearances, captain Spurs for nearly a decade, and win the World Cup with France before leaving for LAFC in 2024 on a free transfer. And no, Lyon never did see that 20% sell-on clause materialise.

3. Luka Modric went on to win six Champions Leagues

Luka Modric joined Tottenham from Dinamo Zagreb in 2008 for £16.5m, which was then a club-record fee. Daniel Levy personally flew to Zagreb to close the deal as Manchester City and Newcastle circled. He became the heartbeat of the Spurs’ midfield, contributing to 38 goals in 157 appearances. Chelsea had multiple bids rejected for him, including £40m in 2011, before Levy finally sold him to Real Madrid for £30m a year later. In Madrid, he went on to become a Ballon d’Or winner, World Cup finalist, and the most decorated player in their history.

2. Heung-min Son is Mr Tottenham

Signed in 2015 from Bayer Leverkusen for £22m, Heung-min Son was initially seen as a marketing stunt to boost Spurs’ profile in Asia. In fact, Leverkusen even rejected an £18m first bid before Levy pushed it up. Like he said, Son arrived as a shy 23-year-old who barely spoke English and left 10 years later a Spurs legend. Son scored 162 goals, won the Premier League Golden Boot, and captained Tottenham to their first trophy in 17 years.

This summer, he departed for MLS side LAFC in a record £19.6m deal at age 33, leaving more than the full fee recouped after a decade of service. Legend.

1. Gareth Bale is Daniel Levy’s greatest purchase and greatest sale

In 2007, Tottenham signed Gareth Bale from Southampton for an initial £5m, potentially rising to £10m based on appearances and success. Originally a left-back, Bale reinvented himself as a winger and lit up the Premier League. In six years, he scored 55 goals in 194 appearances, winning both PFA Player of the Year and FWA Footballer of the Year.

In 2013, he was sold to Real Madrid for £85.3m, a world record fee at the time. Daniel Levy himself admitted Spurs had no desire to sell, but the size of Madrid’s offer and Bale’s own wish to move forced his hand.

The Daniel Levy legacy and what comes next at Tottenham

There are a few other honourable mentions who could easily make this list, like Dele Alli, who many fans would argue deserves a place outright. Robbie Keane, Rafael van der Vaart, and even more recent signings like Cristian Romero and Micky van de Ven, may also count themselves unlucky.

Levy’s legacy as a businessman and negotiator is undeniable, but over time, his methods wore thin with supporters. Constant delays in the market, a habit of settling for less, and rival clubs refusing to deal with his shenanigans ultimately harmed Spurs’ progress. That is why he was asked to step aside rather than leave on his own terms.

With ENIC now set to inject more funds into Tottenham, fans will be hoping that the next chapter in recruitment brings fresh names to rival the best of Levy’s era.