In the 23 years Daniel Levy has been Tottenham chairman, there has been a mixed bag of transfer successes.
Spurs have unearthed some gems over the years such as Gareth Bale and Luka Modric, selling them on for big profits.
However, for every Welsh wizard and creative Croatian, there has been a flop come through into the Tottenham squad.
The Levy era has equipped some Spurs managers with options that simply haven’t lived up to their transfer fee.
Signings may not work out for several reasons, however a fair few just didn’t quite settle in at Hotspur Way.
So with that said, here’s a look at the top ten worst transfers Tottenham have made in the Levy era, with key factors surrounding their price tag, time at the club and the impact they had.
10 – Hossam Ghaly
Some Tottenham fans may not recall midfielder Hossam Ghaly, but his spell at the club was certainly filled with controversy.
Spurs landed the Egypt international from Feyenoord in 2006, however, an incident at Blackburn Rovers is how he is best remembered.
Ghaly was substituted against Rovers in 2007 and proceeded to take off his shirt and throw it on the ground, leading to disciplinary procedures from the club and an apology statement from the player himself.
After that moment, the midfielder didn’t play for Spurs again, leaving in 2009.
9 – Giovani Lo Celso
Tottenham made their loan deal for Real Betis midfielder Giovani Lo Celso permanent in 2020, with hopes that the midfielder would replace the outgoing Christian Eriksen.
An exact transfer fee paid is tough to confirm, however reports have varied between Spurs shelling out £35million-to-£60million for the playmaker.
The Argentina international hasn’t quite reached the heights though, scoring just ten times and bagging eight assists in over 100 appearances for the club.
8 – Ryan Sessegnon
Tottenham shelled out £25million to land Ryan Sessegnon in 2019 from Fulham, with the youngster showing plenty of promise.
At just 17 years old, Sessegnon was a mainstay in the team at Craven Cottage, helping them earn promotion to the Premier League.
The full-back often played on the wing in his early days, scoring 16 goals in the campaign and winning the Championship player of the season.
With hopes of tapping into that potential, Spurs made their move but injuries have impacted the defender severely.
Sessegnon managed just 57 appearances for Tottenham in five years, with nine separate injuries keeping him sidelined.
7 – Roberto Soldado
Tottenham signed Roberto Soldado from Valencia in 2013, hopeful that the striker would elevate them to new levels.
£26million was paid for the Spaniard, who could only muster up 16 goals and 11 assists in 76 appearances for Spurs.
6 – Paulinho
Paulinho is a player that has embarked on an interesting journey through his career.
Tottenham paid £17million for the Brazilian midfielder from Corinthians, with lofty expectations for his career trajectory.
Poor performances led to a two-year stay at White Hart Lane, before leaving the club for Guangzhou Evergrande, in China.
Since then, Paulinho has played for Barcelona and has since returned to Corinthians in the twilight of his playing career.
5 – David Bentley
In 2008, Tottenham dropped a staggering £15million on winger David Bentley from Blackburn Rovers.
Bentley had some bright moments, such as his stunning effort to score against North London rivals Arsenal.
However, with a dip in form, he would quickly become out of favour and was sent on loan spells to Birmingham City, West Ham United, FC Rostov and Blackburn again.
Bentley retired at just 29 years old, scoring five times for Spurs in 62 appearances.
4 – Vincent Janssen
In their search for a strike partner for Harry Kane, Tottenham landed Vincent Janssen from AZ Alkmaar for £17million.
The Dutch forward had cost just £400,000 the summer before at Almere City, representing a huge jump in value.
The end product didn’t quite justify the outlay though, as Janssen failed to impress under Mauricio Pochettino and scored just six goals before leaving for Monterrey in 2019.
3 – Clinton N’Jie
In their search for yet another striker, Tottenham signed Clinton N’Jie as an impressive young option from Marseille in 2015.
The forward joined for roughly £12million, but failed to make any impression as he didn’t manage to score a single goal for the club before leaving in 2017 to rejoin Marseille.
2 – Grzegorz Rasiak
Tottenham spent £3million in 2005 to sign Grzegorz Rasiak from Derby County, with the centre-forward impressing in the second tier.
His time in North London was short and anything but sweet as he made just nine appearances and failed to score or assist in that time.
1 – Tanguy Ndombele
The number one worst signing in the Levy era may well be Tanguy Ndombele, purely for the transfer fee associated with the move.
Tottenham spent a club-record £63million to land the playmaker from Lyon in 2019, and he showed glimpses of that ability.
However, with ten goals and nine assists in 91 appearances for the Lilywhites, there were questions over the deal.
The Frenchman has since spent three consecutive seasons on loan, where he has struggled to convince, likely leading to little return on that large investment from the club.
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