Tottenham Hotspur, and Daniel Levy in particular, have developed a reputation for being hard-nosed in transfer negotiations, often buying low and selling high.
But from Jurgen Klinsmann to Gareth Bale, some of the best players in the world have graced White Hart Lane.
Spurs even got to the Champions League final under Mauricio Pochettino in 2019, where a team featuring more of their best ever acquisitions such as Son Heung-min were beaten by Liverpool in an all-English final.
Tottenham spent €170 million on the likes of Richarlison, Cristian Romero and Yves Bissouma this summer, and while it is too soon for any of them to make this list, they will rub shoulders with some already in it…
Football Transfers looks at Tottenham’s 10 best transfers of the Premier League era…
10) Lucas Moura – from PSG for €28m in 2018
Lucas Moura joined Tottenham from Paris Saint-Germain in January 2018, and unlike so many winter arrivals, hit the ground running at White Hart Lane, scoring on his first start, against Rochdale in the FA Cup.
Often accused of being inconsistent in the seasons since, the Brazilian will nonetheless go down in Lilywhites folklore after firing Spurs into their first Champions League final in 2019. Ajax were leading their semi 2-0 until a Moura hat-trick, which he completed with the final kick of the ball in the 96th minute.
We’ll never get tired of watching this…
An unforgettable night in Amsterdam ✨
Lucas Moura, Tottenham Hotspur legend pic.twitter.com/jcKOqyINY6
— Tottenham Hotspur (@SpursOfficial) August 13, 2022
9) David Ginola – from Newcastle for £2.5 million (€2.8m) in 1997
Sir Bobby Robson had wanted to sign Ginola for Barcelona the season before he swapped Newcastle for Tottenham, but when Kevin Keegan left Tyneside in January 1997 some of his favourites, like Ginola and Les Ferdinand, soon followed him out the door.
Tottenham arguably got the best of Ginola. The French wing wizard was the PFA Players’ Player of the Year and the FWA Footballer of the Year in 1999, becoming the first player ever to win the awards whilst playing for a club that didn’t finish in that year’s top four.
8) Hugo Lloris – from Lyon for €15m in 2012
A France international when they signed him and still the world champions’ No.1 to this day, Lloris arrived from Lyon in 2012 for a relative snip at €15m. A total of 123 clean sheets in 343 games later, and Lloris is widely regarded as one of the best goalkeeper of the modern Premier League era.
Lyon inserted a 20 per cent sell-on clause into his contract. A decade on Lloris looks just as likely to hang up his gloves at Spurs as anything. He’ll take some replacing.
7) Christian Eriksen – from Ajax for €12.5m in 2013
One Tottenham fan took to social media to burn his jersey when Christian Eriksen signed for Manchester United on a free transfer from Brentford this summer, but he is rightly remembered fondly by most Spurs fans.
Christian Eriksen’s move to Man Utd has angered one Tottenham fan 😬
The supporter kept his pledge to burn his Eriksen shirt 🔥 pic.twitter.com/AUns7wBpY3
— Mirror Football (@MirrorFootball) July 5, 2022
A creative genius, Eriksen only cost Tottenham €12.5m when they bought him in 2013, reuniting with former Ajax teammate Jan Vertonghen. Eriksen was twice named the club’s Player of the Year before leaving for Inter Milan in January 2020.
6) Dele Alli – from MK Dons for £5m (€5.6m) in 2015
It’s easy to forget that Dele Alli was once one of the brightest prospects in English football, and Tottenham deserved immense credit for plucking him from relative obscurity with MK Dons in 2015.
A scorer of great goals and, in his 2016/17 pomp a great scorer of goals with 18 in the Premier League – from midfield – Alli was also an England regular until 2019.
His lack of application has left managers from Jose Mourinho to Antonio Conte at a loss since, though, and he is now at Besiktas via a fruitless spell with Everton. Still only 26.
5) Paul Gascoigne – from Newcastle for £2.2 million (€2.5m) in 1988
Ok, we may have to dip back to just before the Premier League era for this one, but Paul Gascoigne did at least play in the Premier League for Tottenham (apologies Dave Mackay).
But Gazza was at his electric best for Spurs, having joined them from Newcastle at Manchester United’s expense in 1988. “He promised to sign for us, and I went on holiday.” Sir Alex Ferguson later recounted. “I got a phone call from Martin Edwards saying he’d signed for Tottenham because they bought his mother a house for £80,000 and, dearie me, I couldn’t believe it.”
Injured his own knee with a reckless challenge on Gary Charles in the 1991 FA Cup final before joining Lazio for €6.2m (equivalent to €13.6m today) in 1992. Football Italia on Channel 4 was started largely to follow his progress, and he subsequently enjoyed a second peak with Rangers.
4) Luka Modric – from Dinamo Zagreb for €18.5m in 2008
Luka Modric has blossomed into arguably the best midfielder in the world at Real Madrid, and he was the first player not named Cristiano Ronaldo or Lionel Messi in 10 years to be awarded the Ballon d’Or when he won it in 2018.
But it shouldn’t be forgotten that Modric was also a world-class operator in his four years with Tottenham. He arrived as the first of 11 summer signings under Juande Ramos in the summer of 2008, but soon outstripped the others.
“He’s a hell of a player and a manager’s dream,” effused Ramos successor ss manager, Harry Redknapp. “He trains like a demon and never complains, will work with and without the ball on the field and can beat a defender with a trick or with a pass. He could get into any team in the top four.”
It turned out Modric could get into the top one in world football, and he has won five Champions Leagues since his €35m switch to Madrid.
3) Jurgen Klinsmann – from Monaco for €2.2m in 1994
Spurs have had world-class operators before and since Jurgen Klinsmann, but the West Germany World Cup winner’s arrival from Monaco in 1994 arguably secured Tottenham’s reputation as a viable destination for top players in the early Premier League era.
Renowned as a cheat in England, he immediately won fans over on his debut, scoring a headed winner against Sheffield Wednesday and immediately celebrating with a diving celebration that has been copied far and wide since.
2️⃣5️⃣ years ago today, @J_Klinsmann introduced THAT celebration! 🙌#THFC ⚪️ #COYS pic.twitter.com/BvPJTmtziI
— Tottenham Hotspur (@SpursOfficial) August 20, 2019
Scored 38 goals in 66 games, sold over 150,000 shirts with his name emblazoned on the back, was inducted into Madame Tussauds Wax Museum and still enjoys cult status among Spurs fans today.
2) Gareth Bale – from Southampton for £10 (€11.8m in 2007)
Not the first player to leave Tottenham for Real Madrid, but quite possibly the most talented to represent Tottenham in the Premier League era, Bale lit up the Premier League and Champions League across his first six season at White Hart Lane.
It’s incredible to think that the Welsh wing wonder was signed from Southampton as a left-back in 2007, and the early headlines weren’t kind, with Spurs winless in Bale’s first nine games for the club. But he soon turned things around, and after being moved into a more attacking role by Harry Redknapp, he never looked back.
We miss the old Gareth Bale 😭
— Football Transfers (@Transfersdotcom) February 5, 2021
Obliterated Maicon – the Brazilian at the time regarded as one of the best right-backs in the world – when Tottenham beat Inter Milan 3-1 in the 2010/11 Champions League group stage, and Real came knocking to the tune of €100m in 2013.
Returned briefly on loan two seasons ago and is now seeing out his career with LAFC.
1) Son Heung-min – from Bayer Leverkusen for €30m in 2015
Modric and Son may have Champions League trophies that have eluded Son Heung-min, but the South Korean has spent the prime of his career at White Hart Lane, and his ceiling has proved to be extremely high indeed.
Making a mockery of the notion of a “Bundesliga tax” ever since his €30m arrival from Bayer Leverkusen in 2015, Son matched the irrepressible Mo Salah for Premier League goals last season, top-scoring with 23 despite playing in the line behind No.9 Harry Kane.
South Korea were playing. So, of course, Son scored 📷pic.twitter.com/Vjn5CYKqxQ
— Football Transfers (@Transfersdotcom) September 27, 2022
Now with 134 goals and 75 assists in 334 games in all competitions with Tottenham, Son is widely regarded as the greatest South Korean, if not the greatest Asian, player of all time.
A Premier League and Champions League runner up with Spur, Son was told by his dad that he had to leave in order to prove he was world class this summer. But he has already done that.