Daniel Levy anniversary: The 20 best Spurs deals of his tenure

Daniel Levy anniversary

It's exactly 20 years to the day since Daniel Levy was appointed chairman of Tottenham Hotspur.

Levy has since overseen a dramatic period of transformation for the north London outfit in which they've blossomed into a genuine European heavyweight. 

Spurs have reached a Champions League final, won the League Cup and completed the transition from White Hart Lane to arguably the most stunning stadium in world football. 

While the Lilywhites have moved through a period of significant change, Levy has developed a reputation as one of the shrewdest negotiators in the game. 

He has long been an enigma of major interest to supporters both within and outside the club and, though he is a divisive figure, much of Spurs' success has been attributed to his dealings in the transfer market. 

With that in mind, GIVEMESPORT have put together a ranking of his 20 best deals to honour his anniversary at the club. 

By taking into consideration performance-based, sentimental and financial factors, we count down the best deals Levy has overseen from 20 to one. 

Take a look below: 

20. Tanguy Ndombele (Bought for £55m)


By no means a bargain but the acquisition of Tanguy Ndombele was an aptly-timed coup.

19. Kevin Wimmer (Bought for £5.4m, sold for £17.5m)

How did Levy hoodwink Stoke City into paying £17.5m for Kevin Wimmer? An insight into what he's capable of on the negotiating table.

18. Rafael van der Vaart (Bought for £9.45m)

One of many deals Levy has conducted with Real Madrid. 

The Dutch playmaker went on to notch 28 goals and 18 assists in 77 appearances for Spurs and achieved cult hero status in the process. 

17. Kieran Trippier (Bought for £3.5m, sold for £20m)

Spurs made a tidy profit on Kieran Trippier after four years of excellent service at right-back.

16. Michael Carrick (Bought for £3.5m, sold for £18.6m)


Levy landed Carrick from West Ham United before the full extent of his potential became apparent. 

He was a top notch metronome for the club and deserved his move to Manchester United.

15. Danny Rose (Bought for £900k)

It's a real shame how Danny Rose's career has descended into anonymity. 

The flying left-back is Spurs' longest-serving player and has played a key role in the club's growth since joining from Leeds United.

14. Mousa Dembele (Bought for £17.1m)

One of the most unique and gifted central midfielders of Spurs' modern era. 

A steal at just £17.1m. 

13. Jan Vertonghen (Bought for £11.25m)

One of a handful of Ajax products that Levy has successfully landed. 

Jan Vertonghen was a Goliath during an eight-year stint.

12. Aaron Lennon (Bought for £1.08m)


Aaron Lennon's delivery may have induced some frustration but his return of 30 goals and 78 assists in 365 games isn't to be sniffed at. 

That's some output for just £1.08m.

11. Dele Alli (Bought for £6m)

The £6m Levy paid for Dele Alli once represented a firm top five contender on this list.

His demise in recent seasons, however, forces him down to what is a generous ranking on recent form.

10. Christian Eriksen (Bought for £12.75m)

Christian Eriksen's departure did somewhat tarnish his reputation at the club but it's impossible to dispute the size of his impact.

The Denmark international scored 69 goals and provided 89 assists in 305 appearances during a six-and-a-half year stint. 

9. Toby Alderweireld (Bought for £14.4m)

Alongside Vertonghen, Toby Alderweireld formed half of one of the most impactful partnerships in the club's recent history.

8. Dimitar Berbatov (Bought for £10.9m, sold for £30.75m)


One of football's most iconic mavericks rose to fame at Spurs following his move from Bayer Leverkusen. 

The £30.75m Levy pocketed from his sale to Manchester United was a huge figure in 2008.

7. Jermain Defoe (Bought for £9.45m, sold for £8.4m, re-signed for £14.8m)

We're into club legend territory.

Jermain Defoe joined Spurs for just £9.45m in January 2004 and went on to bag 143 goals and 31 assists in 362 appearances.

6. Robbie Keane (Signed for £9.45m, sold for £21.6m, re-signed for £15m)

Robbie Kean and Defoe's positions are relatively interchangeable but the former gets the nod in sixth place by virtue of his profit margin.

5. Heung-min Son (Bought for £27m)


Heung-min Son forms part of a tiny handful of world-class Spurs players to have played in the Levy era.

The scintillating South Korea international is now worth £81m, per Transfermarkt.

4. Teddy Sherringham (Bought for £0)

One of the great Bosman ruling transfers was secured through Levy's powers of persuasion.

After signing for Spurs, Teddy Sherringham cited the new Spurs chairman's influence, per BBC.

"It was a very big decision, especially as Sir Alex wanted me to stay.

"But Daniel Levy (Spurs' non-executive director) convinced me it was the right move."

The announcement arrived just over two months after Levy had started the job, and it's the timing and significance of the deal that ranks Sheringham so highly here.

What a way to make your first impression.

3. Luka Modric (Bought for £18.9m, sold for £31.5m)

Levy used all of his foresight to secure a future Ballon d'Or winner in 2008.

The diminutive Croatian was one of the most talented players to set foot at White Hart Lane and left fans fawning over his ability throughout his four-year spell.

2. Gareth Bale (Bought for £10m, sold for £85m)

Following a tepid opening to his career at Spurs, Gareth Bale blossomed into one of the best players in world football.

Levy's decision to raid Southampton for £10m was vindicated through umpteen spectacular goals, sumptuous assists and a £75m profit when he completed his world-record breaking switch to Real Madrid. 

1. Mauricio Pochettino 


The appointment of Mauricio Pochettino wasn't strictly a deal as such, but he thoroughly justifies his place at the top of this ranking. 

No individual has had such a profound and revolutionary effect on the club throughout Levy's reign. 

His pulsating tactical philosophy once made Spurs the most exciting team to watch in English football, and the Argentine's tenure will long be revered as a vital component of the club's rise into Europe's elite. 

Though the decision was considered to be a gamble by some, Levy took a chance on Pochettino in light of his auspicious time at Southampton.

Pochettino's failure to win a trophy when Spurs were in the ascendancy ultimately led to his downfall, but what he achieved on a broader level was far more significant than a piece of silverware. 

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