Highlights

• Tottenham’s record signing Tanguy Ndombele has been a financial disaster and he now looks set to leave the club
• He wasn’t the only midfielder on Spurs’ radar as they looked to replace Mousa Dembele
• Other potential midfield signings for Tottenham included Youri Tielemans, Florian Grillitsch and Franck Kessie

Back in summer 2019, Tottenham Hotspur coughed up a club-record £63m fee to sign Tanguy Ndombele from Lyon. It remains one of the top 50 most expensive transfers in the history of English football, but also one of the biggest financial disasters of Daniel Levy’s tenure as chairman of the north London club.

Indeed, Levy broke a habit of a lifetime that summer, trying to capitalise on Mauricio Pochettino’s Tottenham side unexpectedly reaching the 2019 Champions League final by investing heavily in a new star midfielder, while also bolstering the squad with the additions of Ryan Sessegnon and Jack Clarke. Tellingly, Spurs had previously gone 18 months without signing any first team players, so a new record acquisition was very much a deviation from the norm.

But the move backfired completely. Levy dispensed of the manager who brought Ndombele to Spurs just a matter of months later, while successors Antonio Conte, Jose Mourinho and Nuno Santo all struggled to get a tune out of him.

The Frenchman has made just 62 starts in four years, having been loaned back to Lyon in January 2022 and then farmed out to Napoli for the entire of last season. Reports of a poor attitude continue to this day and Spurs are said to be looking to finally offload Ndombele for good this summer.

But going back four years, Ndombele certainly wasn’t the only midfielder on Tottenham’s radar as they sought a replacement for Mousa Dembele, who had left the club for the Chinese Super League in January.

So who could Spurs have signed instead, and where are they now? We take a look below…

6

Yves Bissouma

Yves Bissouma was just another one Brighton’s recruitment team got right. The Mali international joined the Seagulls from Lille in 2018 at the age of 21, and following an initial settling in period, the central defensive midfielder was spellbinding for the South Coasters, whose £15 million move proved to be another piece of savvy, emphatically executed business from Brighton.

Now at Tottenham, having signed for the club for £35m during the 2022 summer transfer window, Daniel Levy may have been left kicking himself having been interested in the player four years earlier, where he could have landed him for a fraction of the price, and an even smaller fraction of what he paid for Ndombele twelve months later.

5

Youri Tielemans

In one of the finest pieces of business in the free market this summer, Aston Villa made the major coup of scooping Belgium international, Youri Tielemans on a free transfer from Midlands rivals, Leicester City. The midfield maestro was pivotal in Leicester’s concerted effort at breaking the Premier League top six mould, and making it a top seven. He also scored a rocket for the Foxes in the 2021 FA Cup final to secure the club its first-ever FA Cup crown.

The acquisition of the hot prospect didn’t come easy either, with both Manchester United and Tottenham Hotspur in serious pursuit of the player heading into the 2019 summer transfer window following a six-month loan at the King Power Stadium. The midfielder could have been a viable option over Ndombele, with the pair experiencing quite the contrasting Premier League fortunes, but he favoured staying with the Foxes.

4

Florian Grillitsch

Midfielder Florian Grillitsch has enjoyed quite the steady professional career in the Bundesliga. The Hoffenheim star made 152 appearances for the German club during his five-year stay before heading off to explore new opportunities for Ajax in the Eredivisie during the 2022 summer window.

Now back at Hoffenheim, following a disappointing period in the Netherlands, the player may be left wondering what could have been if he had signed for Tottenham as was rumoured during the 2019 January transfer window. His contract was said to include an £18 million release clause but the transfer chatter came to nothing.

3

Andre Gomes

Despite being a man out-of-favour in Catalonia, Andre Gomes was still very highly rated elsewhere and seemed keen on the idea of proving himself in the Premier League when joining Everton on loan in summer 2018.

He seemingly did just that as it was reported the following year that Daniel Levy and Tottenham were interested in taking the centre-midfielder off Barça’s hands for an alleged fee of £30 million, half the price paid for Spurs flop, Ndombele.

Unfortunately, Gomes’ Everton career hasn’t gone to plan. Ironically suffering a serious injury against Tottenham, the Portugal international struggled for minutes at Goodison Park and spent last season on loan at Lille.

He’s now into the last year of his contract with the Toffees, suggesting a move will take place this summer.

2

Franck Kessie

The Ivorian was once a hotly-tipped prospect who Serie A side Atalanta had plucked from relative obscurity. Earning himself a succession of big moves to AC Milan and Barcelona, Franck Kessie now finds himself plying his trade in Saudi Arabia following a move to Al Ahli.

Prior to his permanent move to Milan, Kessie was widely touted to be on the radar of Tottenham as a direct replacement for Mousa Dembele. Instead, Kessie stayed on at the San Siro full-time where he’d go on to establish himself as one of the top stars of Italian football, providing a consistent supply of goals from midfield.

1

Donny van de Beek

The Dutchman was a pillar in Erik ten Hag’s Ajax side that reached the Champions League semi-finals in 2019, only to be stopped by a Lucas Moura masterclass.

The midfield prodigy charted his rise alongside the likes of Mattheus De Ligt, Frenkie De Jong and Andre Onana, except unlike the aforementioned who have gone on to achieve impressive feats in their careers so far, Van de Beek’s time as a professional footballer peaked at the Johan Cruyff Arena. He has been on a downward spiral ever since, with his stint at Manchester United spelling disaster.

A fruitless loan move to Everton has meant the midfielder’s time in England has been massively underwhelming, but could it have been different if he had joined up with Pochettino at Tottenham? Van de Beek had been linked with a move to Spurs towards the end of the 2019 season, with Tottenham said to have been impressed with his performances against them in the Champions League.

But the Dutchman stayed put, before moving to Old Trafford a year later.