Ranking Daniel Levy’s top 10 BEST and WORST Tottenham signings

Following Daniel Levy’s decision to walk away from his role as Tottenham chairman, TEAMtalk has ranked what we think are the 10 best and worst signings of his long tenure in north London.

Levy was appointed in March 2001 and leaves nearly 25 years on, although he does so with his head held slightly higher after the Europa League success last season.

The 63-year-old was the Premier League’s longest-serving chairman and earned an estimated £50m-plus during his time in charge, but he was also the target of regular protests from Tottenham fans, especially last season when an ill-equipped squad ended up finishing 17th in the Premier League.

A new dawn could now be on the horizon in north London, but for now, let’s take a look back at Levy’s business over the years…

Top 10 best signings

10. Dele Alli

Transfer fee: £5m

From: MK Dons

Appearances and goals: 269/67

It’s a massive shame the way things have turned out for Dele, but what a player he was during that three-year stint between 2015-2018 when Tottenham were genuinely pushing for the Premier League title.

Considering the peanuts they paid for him, the payoff was a big one – before things sadly started to go downhill.

9. Dimitar Berbatov

Transfer fee: £10.9m

From: Bayer Leverkusen

Appearances and goals: 102/46

The silky technician was an incredible player to watch, even if he only had two seasons in north London before Man Utd eventually came calling in 2008.

Levy negotiated a near £20m profit on the sale, with legendary Old Trafford boss famously writing in his autobiography that dealing with the Spurs supremo at the time “was more painful than my hip replacement”.

A Levy special for sure!

8. Hugo Lloris

Transfer fee: £11.8m

From: Lyon

Appearances and goals: 447/0

Incredible value for money for the France World Cup winner, who spent over a decade in north London and spent eight as captain of the club.

Unfortunately for Lloris, he failed to lead the club to any silverware in that time and his form dropped off badly towards the end. However, he will still go down as one of the best goalkeepers the club ever had.

7. Robbie Keane (twice)

Transfer fee: £7m and then £16m

From: Leeds, Liverpool

Appearances and goals: 306/122

One of the most popular players ever to pull on a Spurs shirt and Keane has admitted previously that the best spell of his long career came in that first stint in north London.

The former Republic of Ireland international remains a regular at Tottenham legends games and is still a quality performer, even at the age of 45.

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6. Jermain Defoe (twice)

Transfer fee: £7m and then £15.75m

From: West Ham, Portsmouth

Appearances and goals: 362/143

Another legendary striker, so good they signed him twice.

Defoe was a lethal finisher who linked up so well with the likes of Keane and Peter Crouch during his time at the club. He remains a hugely popular figure with the fanbase even now.

5. Rafael van der Vaart

Transfer fee: £8m

From: Real Madrid

Appearances and goals: 77/28

Van der Vaart only spent just over two seasons at Tottenham but made a massive impact while he was at the club, having been an absolute bargain signing from Real Madrid.

Considering some of the quality performers he had at his disposal, Harry Redknapp was adamant about the best player he signed during his time as Tottenham boss.

He previously said: “Someone like Rafa van der Vaart was a fantastic signing for me at Tottenham in a last-minute deal. A great player, came in and set the place alight, he was amazing.”

4. Christian Eriksen

Transfer fee: £11m

From: Ajax

Appearances and goals: 305/69

One of the bargains of the Premier League era for sure, and it’s criminal that Tottenham were unable to win a trophy during his seven seasons at the club.

Eriksen was at his very best when Spurs were flying under Pochettino, supplying the bullets for the likes of Harry Kane and Son Heung-min.

It’s a shame it all came to a slightly bitter end when he openly admitted that he would run down his contract and leave on a free in the summer of 2020. He ultimately joined Inter with six months left on his deal in that January.

3. Luka Modric

Transfer fee: £16.5m

From: Dinamo Zagreb

Appearances/Goals: 160/17

Many Tottenham fans would agree – especially those who saw him in the flesh – that Modric was an absolute technical marvel and one of the most gifted players to ever pull on the shirt.

When he signed in the summer of 2008, Spurs equalled their club record in a deal that raised plenty of eyebrows, but he goes down as one of the most astute pieces of business that Levy ever did.

Given his smaller frame, his longevity in the game is quite remarkable, with the 39-year-old still turning out at the top level for AC Milan.

2. Gareth Bale (twice)

Transfer fee: £10m and then a loan

From: Southampton, Real Madrid

Appearances/Goals: 237/71

In terms of the sheer bought and sold aspect, Bale would be the clear No.1, but it’s not all about that when assessing these inclusions – even if that would have been right up Levy’s street!

The ‘Bale curse’ early in his Tottenham career ended up becoming a thing of myth after he transitioned from being a struggling full-back into one of the most explosive wingers in the game.

Brazilian full-back Maicon likely still wakes up in hot sweats over the way Bale demolished him in Champions League clashes with Inter.

And while he is No.1 on many lists that have been done in the wake of Levy’s exit, Bale just misses out on ours.

1. Son Heung-min

Transfer fee: £22m

From: Bayer Leverkusen

Appearances/Goals: 454/173

One of the best Premier League forward players of the last decade without a shadow of doubt and a true Tottenham legend.

It was so fitting that Son was the player to lift the club’s first major trophy in 17 years in Bilbao after all the blood, sweat and tears during his time in north London.

His link-up with Harry Kane during their time together saw them become one of the best tandems in Premier League history, while he then took on the captaincy after Lloris and Kane moved on.

A great player, a great guy and an incredible Levy signing.

*Honourable mentions

As always with these types of lists, there are always players that miss out that could easily have been in. To that end, the defensive tandem of Jan Vertonghen and Toby Alderweireld certainly deserve a bit shout out, as do Mousa Dembele and Kyle Walker amongst others.

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Top 10 worst signings

10. Grzegorz Rasiak

Transfer fee: £3m

From: Derby County

Appearances/Goals: 9/0

The Poland international was signed in 2005 but offered next to nothing during his short period in north London.

Indeed, Rasiak ended up being loaned out to Southampton and joined them in a permanent deal in the summer of 2006, with Levy suffering a £1m loss on that deal.

9. Yves Bissouma

Transfer fee: £30m

From: Brighton

Appearances and goals: 100/2

This might be a slightly controversial one for some Tottenham fans, especially given the fact that he is still currently employed by the club, but Bissouma has been a massive disappointment – if truth be told.

He was an incredible talent at Brighton and Spurs looked like they had snapped up an absolute bargain in 2022. However, besides a couple of spells where he came close to that level he had with the Seagulls, the Mali international has been a major letdown.

Yes, he performed well in the Europa League semi-finals and final, but Thomas Frank identified as soon as he walked through the door that he needed to upgrade the No.6 role, hence the arrival of Joao Palhinha.

8. Ryan Sessegnon

Transfer fee: £25m

From: Fulham

Appearances and goals: 57/3

A talented player who was so unlucky with injuries, but Sessegnon ultimately ended up being a bust signing.

7. Clinton N’Jie

Transfer fee: £8.3m

From: Marseille

Appearances and goals: 14/0

N’Jie came in from Marseille back in 2015, having earned a reputation as a real emerging talent in French football.

He ended up spending two seasons in north London, the second of which was a loan back to Marseille, before he rejoined them permanently.

6. Davinson Sanchez

Transfer fee: £42m

From: Ajax

Appearances and goals: 207/5

Arriving in 2017, Sanchez was lauded as a huge talent and his signing was viewed as a bit of a coup for Levy at the time.

In truth, he looked like he would be a great addition in his early days, although he was playing in the middle of a back three with Vertonghen and Alderweireld either side of him.

As soon as he was utilised in a back four there were mistakes galore, and he often looked really uncomfortable in possession too.

What looked like good business at that time ended up being a near £35m loss after Sanchez had played under multiple Tottenham coaches.

5. Vincent Janssen

Transfer fee: £17m

From: AZ Alkmaar

Appearances and goals: 42/6

In their search for a reliable backup for Kane’s ankle troubles at the time, Spurs plucked Janssen from Alkmaar after an impressive scoring stint in Holland.

However, he really struggled to adapt to English and ended up in Mexico with Monterrey just two years later.

4. Paulinho

Transfer fee: £17m

From: Corinthians

Appearances and goals: 67/10

A Brazilian who came to the club with a big reputation, as Spurs started spending the money they recouped from Gareth Bale’s mega sale to Real Madrid.

However, he lasted just two years before being shipped off to the Chinese Super League.

3. Giovani Lo Celso

Transfer fee: £27-55m

From: Reeal Betis

Appearances and goals: 108/11

It’s never actually emerged how much Levy paid to get Lo Celso on board back in 2020 after an initial loan stint, with reports varying from as little as £27m up to over £55m!

Either way, the highly-rated Argentine was a massive disappointment, failing to convince the likes of Jose Mourinho, Antonio Conte and Ange Postecoglou that he was worthy of keeping around.

2. Roberto Soldado

Transfer fee: £26m

From: Valencia

Appearances and goals: 76/16

The club’s record signing at the time of his arrival in the summer of 2013, off the back of the Bale sale, Soldado was a major flop in north London.

Prior to the breakthrough of Kane, Soldado was tasked with leading the line for Spurs but was not particularly good at it. He lasted just two seasons before heading back to Spain.

1. Tanguy Ndombele

Transfer fee: £60m

From: Lyon

Appearances and goals: 91/10

Abundance of talent – check. Bad attitude – double check.

Tottenham spent a new record fee to sign the French playmaker in 2019, off the back of their Champions League final failure months earlier.

Pochettino played a bit part in convincing Ndombele that he could improve his game in north London, but ended up being sacked not long after, and the attacking midfielder never really got his Spurs career going after that.

There was a spell under Mourinho where he started to flourish, but rumours of attitude problems were rife and the club ended up terminating his contract in 2024 – not getting a penny back for his services as a result.

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