Tottenham are prone to making a faux-pas or two in the transfer market but even by their standards questions have to be asked about Tanguy Ndombele.
Dropping £55million on the Frenchman, who can’t seem to convince any manager that walks through the door that he is worth persisting with, is looking like a woeful investment right now – and fans have had enough.
Booed off for a below-par display against struggling League One side Morecambe is a new low and some on social media were quick to condemn Ndombele as the club’s worst ever signing.
French midfielder Tanguy Ndombele was loudly booed by Spurs fans as he walked off the pitch
While it is bad, and Spurs are said to be open to offers for the central midfielder, he would not be alone in failing to make it work at Tottenham.
Roberto Soldado still finds himself haunted after joining from Valencia, Sergei Rebrov was himself a record buy only to be booted into touch by Glenn Hoddle and one player went four and a half years without a single second of competitive action for Tottenham.
With that in mind, Sportsmail goes back through the archives to work out who is Tottenham’s biggest transfer regret…
10. Benjamin Stambouli
Joined in 2014 for £4.7m
The French midfielder arrived from Montpellier and expectation was high. Oh how foolish that seems now.
In fairness, Mauricio Pochettino wanted Morgan Schneiderlin but couldn’t prise him away from Southampton.
That then saw a late scramble for a defensive midfielder and the wheel must have stopped on Montpellier title winner back in 2012, Stambouli.
Benjamin Stambouli (left) was a deadline day arrival and lived up to the ‘panic buy’ status
‘It’s a dream to play in the Premier League and with Tottenham,’ he said, ‘it adds another dimension.’
Actually turned out to be more of a nightmare that is the exact type of experience that would be scratched from a CV.
The Frenchman started just four league games during his time in England and got four yellow cards to match.
The best thing Tottenham did with this deal was convince Paris Saint-Germain to give them £6million to take Stambouli off their hands. Season to forget.
Joined in 2008 for £1.9m
In a line-up featuring Alan Hutton, Jonathan Woodgate and Chris Gunter, Gilberto would likely have scoffed at the idea that it would be his career that would nosedive.
Gilberto was flying the flag for Brazil and when he overcame injury, which he joined with in that January window, he made his debut in the UEFA Cup in March, becoming the first Brazilian to play for the club at first-team level.
To those back in Brazil watching on at history being made, it was excruciating.
Gilberto was at fault for PSV Eindhoven’s goal – the only one of the game – and he was hooked off by boss Juande Ramos at half-time.
He did at least score and so deserves some credit for that, coming on in a 4-0 win over West Ham to net the third goal.
Gilberto (far right) made history as Spurs’ first Brazilian but it was a ‘nightmare’ stint at the club
But just three appearances in the following 2008-09 season ensured the writing was on the wall and he was promptly sent packing back to Brazil, where he joined Cruzeiro after his contract was terminated.
In fairness, he actually apologised for the ‘nightmare’ stint in an interview back in 2018, so we’ll show similar remorse in these rankings.
‘It’s true, I had a nightmare at Spurs. But I’d done well in Germany. I played for my country, and I’d won stuff in Brazil,’ Gilberto told ESPN. ‘Tottenham came in, and I saw it as a chance to have a proper crack at some silverware.
‘I remember my debut against PSV. I tried to dribble past Jefferson Farfan. He nicked the ball from me and scored. From that moment, it was all downhill. I tried my best at training and hoped that things would turn around.
‘I want to say sorry with all my heart to the Tottenham fans. I’m gutted that it didn’t work. I would have loved to have stayed, but I got branded very quickly. There were some great people at the club, but it was a bad time for me personally.’
8. Clinton N’Jie
Joined in 2015 for £8.3m
Another real headscratcher here… but you could say that about all of those that made the cut.
Snubbing Arsenal to take a five-year contract across north London with Tottenham, this pacey striker seemed – seemed being the key word – to have the attributes to excel in English football.
And yet it was a disaster, whichever way you dice it up.
Clinton N’Jie made the move from Lyon but never managed to score a goal for Tottenham
The Cameroonian never made a single start in the Premier League for Tottenham, all eight of his appearances coming off the bench.
He never managed a single goal for Tottenham, either.
His highlight, you ask? Well, he got an assist for Erik Lamela against Manchester City…
To cut him some slack he was badly hampered by a knee injury which he sustained in the December of 2016.
That sidelined him for three months and he never really recovered himself in the eyes of Mauricio Pochettino, eventually being shipped out on loan to Marseille after one season before making that permanent 12 months later.
Joined in 2013 for £17m
The minute Paulinho was nicknamed ‘The Brazilian Lampard’ you just knew disaster was afoot.
‘This comparison is a responsibility I will take, I will not run away from it,’ he said when he arrived from Corinthians in the summer of 2013 as part of the seven signings funded by Gareth Bale’s Real Madrid move.
Andre Villas-Boas was smitten with Paulinho, then a club record signing at £17m before they broke it twice more in the same window.
Winning Man of the Match in his Premier League debut, a 1-0 win over Crystal Palace, was a good early sign but it was something of a false dawn for the Brazilian international.
This wasn’t Gilberto Part II but even so, he fell so far short of expectations.
Paulinho arrived with so much promise but, likened to Frank Lampard, he majorly disappointed
On a wage of £55,000 a week and turning up as a Copa Libertadores and Club World Cup winner, he was expected to stand out, and make a tangible difference.
Villas-Boas’ sacking in December – prior to that the boss had started Paulinho in every league match before he got suspended in the 5-0 loss at home to Liverpool.
Following a brief caretaker spell of Tim Sherwood, when Pochettino took over Paulinho was hamstrung by a manager who didn’t believe in him.
Paulinho started only three league games under Pochettino and his stock had plummeted. Fans had expected an international star but seemed to be seeing a pretender by the same name.
When he completed an eye-opening £10m switch to Guangzhou Evergrande, then the reigning Chinese Super League champions, there was much surprise at the return. His spell had been so disappointing that a £7m loss was viewed as not too bad all things considered.
6. David Bentley
David Bentley is remembered for his wonder goal vs Arsenal but, that aside, he fell well short of expectations across five years
Joined in 2008 for £15m
Speaking of nicknames, the ‘next David Beckham’ doesn’t half paint a target on someone’s back and when Bentley walked away from football at the age of 29 there were a number of questions on where exactly it all went wrong.
In five years he managed 62 games at Tottenham which is startling.
Bentley had caught the eye with Blackburn and was generating plenty of interest.
Tottenham won the race but he soon fell down the pecking order with others, such as Aaron Lennon, proving far more reliable in midfield.
Between 2011 and 2013, when he chose to hang up his boots, Tottenham sent Bentley on a wild goose chase to try and find the form to reignite his career.
Off he went to Birmingham, West Ham, Blackburn and later, Rostov in Russia, of all places. Nothing worked and after falling out of love with the game he called it a day and now looks after various businesses, including running a bar and restaurant over in Spain.
Would be harsh to put him higher when his first league goal for Tottenham was a 43-yard stunning volley in the North London derby against Arsenal, in an epic 4-4 draw in October 2008.
5. Vincent Janssen
Joined in 2016 for £17m
Tottenham aren’t alone in this but they don’t half fall flat on their face in search of top-level strikers.
Janssen was building up quite the hype in Holland when he netted 29 goals in 40 games for AZ Alkmaar.
Tottenham bought into that excitement to the tune of £17m and perhaps wished they had held off after a three-year spell in north London that everyone is keen to wipe from their memory.
Janssen managed 42 games in all competitions for Spurs in total, with six goals.
Vincent Janssen put the blame for his dismal three years on being underappreciated by Spurs
Admittedly, 38 of those appearances came in his first season, as did all six of the goals.
It soon went rapidly down hill – managing just 40 minutes of action in his last two seasons, with a loan at Fenerbahce sandwiched in as well.
Asked where it went wrong at Tottenham years later, Janssen felt he was badly used and under-appreciated.
He told VTBL: ‘It was not the period I was hoping for at Tottenham. As a 22-year-old boy from AZ this was a great step, but I didn’t get the minutes there that I expected.
‘Also, I did not reach my [best] level there. Ultimately you want to play again, be a footballer and be appreciated.’
4. Roberto Soldado
Joined in 2013 for £26m
We mentioned earlier that Tottenham broke their transfer record to get Paulinho before it was broken twice in the same window thereafter.
One of those was Soldado, joining from Valencia for £26m.
He arrived with pedigree and was taken more seriously than someone like Janssen, who arrived years later.
Soldado had scored 59 goals in 101 LaLiga games for Valencia and was widely known as one of the more impressive forwards in Spain at that time.
Cue his move to England.
Roberto Soldado (middle) had pedigree in Spain but he has been left haunted by Spurs spell
Only, in two miserable – and we are unable to use any other word for it – years in north London, Soldado managed three Premier League goals from open play. Three.
In total he had seven Premier League goals to his name before he packed up back for Spain, desperate to escape the hell that had swallowed him.
‘It’s like a thorn in my side and always will be as I wasn’t able to find a solution and give my best performance,’ he told the i back in 2020.
‘I got to a point where I was lost. In the second year I said to myself, “I can’t do this any more, I’ve been an important player in Spain and I can’t be here any more.” I’d got lost as a player and needed to go back to LaLiga.’
Back thriving now with Granada, Soldado will be keen to wipe all memory of his Spurs stint.
3. Sergei Rebrov
Joined in 2000 for £11m
Where to start with Sergei Rebrov?
The all-time top scorer in the Ukrainian Premier League looked electric alongside Andriy Shevchenko when the pair played for Dynamo Kiev.
Here was George Graham’s top target and fans were excited at Rebrov’s potential, particularly after seeing Spurs shatter their transfer record, which had been £6m for Les Ferdinand previously.
Handed a five-year contract as a show of faith, everything was looking good for Rebrov, until he actually had to go out and perform and well… he didn’t.
Hitting the bar on his debut after coming on from the bench gave a glimpse into his magic but that sort of thing was fleeting during two dismal seasons.
Sergei Rebrov was Tottenham’s record buy at the time but was discarded by Glenn Hoddle
Then 25, he was of a slight build and proved too easy for defenders in England to bully.
Just nine league goals in his first season at Tottenham wasn’t good enough for a player who broke the club transfer record.
But when Glenn Hoddle took over that was that and Hoddle put his faith in Teddy Sheringham to score the goals.
Rebrov managed to start just nine league games in 2001-02 and never managed a single appearance in 2002-03.
By the time he was offered an escape route to Fenerbahce he’d only managed 10 goals in 59 Premier League games. A bitter disappointment all round.
2. Tanguy Ndombele
Joined in 2019 for £55m
Spared top spot – you’ll soon see why – but Tanguy Ndombele has been a complete disaster since turning up in north London.
Tottenham shattered their transfer record to the tune of £55m to get Ndombele and now two and a half years later they are wondering whether to cut their losses.
The midfielder’s future at the club appears firmly up in the air after he was booed by his own fans having been hauled off against League One Morecambe in the FA Cup, which must have proven a sobering end to his weekend.
The 25-year-old was handed a rare starting spot against Morecambe but failed to impress and was part of a triple change made by Spurs boss Antonio Conte as his side trailed 1-0 on the hour mark.
Tottenham will listen to offers for Tanguy Ndombele (right) as his time in London disappoints
Ndombele arrived from Lyon with much promise, hope of being the bull-dozing midfielder that could go on to show up rivals higher up the league.
But that just hasn’t happened and as he slowly trudged off the field before heading straight down the tunnel, much to the home crowd’s annoyance, it was hard to argue he has any sort of future in north London.
Jose Mourinho wasn’t sold, Nuno Espirito Santo didn’t look interested and Conte is hardly a patient man for these sorts of things.
Asked about Ndombele going off to a chorus of boos, Conte said: ‘This type of situation happens in football. You have to be good to try to change your opinion if someone is disappointed with you. It’s normal.
‘I was a player and it happened sometimes to me that someone was unhappy with my performance. This is our life. We have to continue to work and try to be better next time.
‘We have to know very well that if we perform well, the fans are happy. If you don’t perform well, the fans are not happy. This is football.’
1. Bongani Khumalo
Joined in 2011 for £1.5m
Well, here is a man fit to where the crown as Tottenham’s worst ever signing.
Forget the nominal value of just £1.5m and focus more on the fact that in four and a half years Bongani Kjumalo failed to make a single competitive appearance for Tottenham.
Khumalo, a defender, joined Tottenham in the 2011 January transfer window from South African side Supersport United.
In comparison to some of the other names on this list, his credentials were significantly less convincing but, given the benefit of the doubt, Khumalo was welcomed with open arms.
To the Tottenham fans who remember Khumalo, fair play, you’re worthy of a place on any quiz team.
Bongani Kjumalo (right) never played in a competitive match for Spurs in four and a half years
To not get a single minute of competitive football in almost five years is actually staggering.
They didn’t even want him in and around the squad after seeing him in pre-season, sending him on five loans to Reading, Preston North End, Doncaster Rovers, Colchester United and, lastly, a stint in Greece with PAOK.
It’s also funny that he sees his best career moment as his time at Tottenham – despite no competitive appearances.
He once told Sport24: ‘The move was the highlight of my career, even though I have had a number of them in my life. I grew as a player and, generally, as a man in this world.’
Whatever you say, Bongani…