During the Premier League era, Tottenham Hotspur have often struggled to keep hold of their star players.
But Spurs chairman Daniel Levy is famed for his ability to drive a hard bargain and has made a lot of money through player sales.
We’ve taken a look at the 10 most expensive sales in Tottenham’s history and how those players fared after leaving north London.
Note: we’ve included potential add-ons in the totals.
10. Kevin Wimmer – £18m
Wimmer only had a bit-part role at Tottenham but they somehow managed to convince Stoke City to part with £18million for the defender in 2017.
He endured a disastrous debut season in 2017/18, making 17 Premier League appearances as the Potters suffered relegation from the top-flight.
The Austria international then spent time on loan at Hannover, Mouscron and Karlsruher SC before his Stoke contract was terminated in 2021.
9. Michael Carrick – £18.6m
Manchester United identified Carrick as a long-term replacement for Roy Keane and eventually agreed a £18.6million deal with Tottenham in 2006.
“I must say negotiations were very difficult and went on for ages,” Sir Alex Ferguson told MUTV. “I always remember I thought it was done and David Gill phoned me on the golf course to say they want more. Typical Daniel Levy!”
The deal represented a huge profit for Spurs, who signed the midfielder from West Ham United for just £2.75million in 2004.
But it also proved to be a great deal for Manchester United as he won five Premier League titles, two League Cups, an FA Cup, the Champions League, the Europa League and the FIFA World Club Cup during his 12 years at Old Trafford.
Michael Carrick is one of the most underrated players that the Premier League has ever seen, the fact that he only got 34 caps for England is criminal. 🤯
— Football Tekkers (@BallTekkers) January 13, 2023
8. Kieran Trippier – £20m
After starring in England’s run to the semi-finals of the 2018 World Cup, Trippier suffered a dip in form with Tottenham in 2018/19.
Mauricio Pochettino then decided to cash in on the England international, selling him to Atletico Madrid in a £20million deal.
He rediscovered his best form under Diego Simeone’s tutelage and played a key role in their La Liga title triumph in 2020/21.
The right-back made 86 appearances for Atletico before returning to the Premier League with Newcastle United in January 2022.
7. Robbie Keane – £20.3m
After Liverpool declared a public interest in Keane in the summer of 2008, Levy made an official complaint to the Premier League.
But the boyhood Liverpool fan handed in a transfer request and eventually got his dream move to Anfield.
“I have already made my opinion clear on the nature of this transaction,” Levy said after the move was finalised.
“I don’t regard it as a transfer deal – that is something which happens between two clubs when they both agree to trade – this is very much an enforced sale for which we have agreed a sum of £19million as compensation plus a potential further £1.3million in additional compensation.”
The striker failed to justify that price tag, scoring seven goals in 28 appearances before rejoining Tottenham in January 2009 for a fee of £12million.
6. Steven Bergwijn – £26.4m
Bergwijn struggled for regular first-team action during his two-and-a-half years at Tottenham and was deemed surplus to requirements by Antonio Conte.
The PSV Eindhoven academy graduate controversially returned to the Netherlands and signed for their rivals Ajax in a £26.4million deal in 2022.
He finished his debut season with 16 goals and six assists in all competitions and has now been named the new club captain.
5. Luka Modric – £28.2m
Having refused to sell Modric to Chelsea in 2011, Tottenham reluctantly accepted Real Madrid’s offer of £28.2million in the summer of 2012.
The Croatia international took a little while to settle in Madrid and was infamously voted as the worst signing of the season, alongside Barcelona’s Alex Song, by Spanish newspaper Marca in December 2012.
He turned things around and has since won 23 trophies for the club, including five Champions Leagues and three La Liga titles.
The 37-year-old, who has made over 450 appearances for Madrid, also won the Ballon d’Or award in 2018 and is widely regarded as one of the greatest midfielders of all time.
4. Dimitar Berbatov – £30.75m
Following a summer of protracted negotiations, Tottenham finally agreed to sell Berbatov to Manchester United on the final day of the 2008 transfer window.
“That whole experience was more painful than my hip replacement,” Ferguson said when reflecting on the £30.75million deal.
The former Bulgaria international scored 56 goals in 149 appearances in all competitions and claimed the Premier League Golden Boot in 2010/11.
His goals helped United win two Premier League titles, a League Cup and the Club World Cup, and he returned to London with Fulham in 2012.
This Dimitar Berbatov goal against Liverpool back in 2010 😱
— B/R Football (@brfootball) January 17, 2021
3. Kyle Walker – £50m
After failing to sign Dani Alves in the summer of 2017, Manchester City manager Pep Guardiola then switched his attention to Walker.
City were initially reluctant to go above £40million but they agreed to pay Tottenham an initial £45million plus another £5million in bonuses.
He has been a pivotal figure in City’s recent success, helping them win five Premier League titles, two FA Cups, five League Cups, the Champions League and the UEFA Super Cup.
The right-back, who has made over 250 appearances for City, was recently linked with Bayern Munich but now looks set to extend his stay at the Etihad.
2. Gareth Bale – £85.3m
Bale won the Premier League Player of the Year award in 2012/13 and his impressive performances attracted interest from Real Madrid.
While Levy insisted that the winger wasn’t for sale, Madrid came up with a then-world record transfer offer that was just too good to resist.
Bale enjoyed a trophy-laden career at the Bernabeu, winning five Champions Leagues, three La Liga titles, one Copa del Rey, one Spanish Super Cup, three UEFA Super Cups and three Club World Cups.
The former Wales international became a divisive figure among supporters but still scored 106 goals for the club, including a brace against Liverpool in the 2018 Champions League final.
🏴⚡️ 5 years ago today: Gareth Bale's goal vs Liverpool in the UCL final. Simply outstanding. pic.twitter.com/UgryprhR5t
— EuroFoot (@eurofootcom) May 26, 2023
1. Harry Kane – £86m
After becoming Tottenham Hotspur’s all-time top goalscorer in 2022/23, Kane then decided to leave the club in pursuit of silverware.
Despite the fact that he was entering the final year of his contract and would have been available for free in July 2024, Spurs still set a high asking price.
The 30-year-old striker eventually moved to Bayern Munich in a deal worth an initial £86million and another £20million in potential add-ons.
His Bayern debut ended in a 3-0 defeat to RB Leipzig in the German Super Cup, but he registered a goal and an assist on his Bundesliga debut.