Tottenham Hotspur are all over the transfer gossip so far this window, having already signed Ivan Perišić and Fraser Forster on frees, with Yves Bissouma having now passed his medical.
With three promising signings already made, it might look like Tottenham are a club that knows exactly what needs to be done in the transfer window.
In some respects this is true. The club bought Gareth Bale for £7million and flogged him for a record £85million. Meanwhile, top players like Heung-Min Son and Cristian Romero now fill their ranks, players who clubs at the very top of world football would snap up in a heartbeat given half a chance.
But for all these successes, the North Londoners have also had their fair share of complete and utter clangers.
Read on for some of Tottenham’s most disastrous transfers in recent memory.
Potentially the worst of the bunch, Janssen signed for the club for a whopping £20million, promising youth and Premier League-ready sturdiness when he signed from Dutch outfit AZ.
But in his three years with the club he managed just 31 league games, returning a measly two goals.
He joined Monterrey for a surprising £8million in 2019.
This one truly is heartbreaking for Spurs fans. The club's record signing at the time of writing – for £53million – no one would doubt Ndombele’s technical gift, an ethereal ability to twist and trip out of danger and into space that no one else knew was there.
But the former Lyon man couldn’t get his rhythm going, falling out with Jose Mourinho and receiving criticism for not being fit.
It seems unlikely he’ll pull on a Spurs shirt again, despite the talent.
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The nimble Frenchman promised to bring a new lease of wide energy to Spurs’ attack.
Spurs bought him for just under £10million in 2017 before sending him out on loan twice.
They eventually gave up on him in 2019, flogging him to Besiktas for around £4million.
He seems to have turned his fortunes around a bit in Turkey though, with 15 goals in 74 goals.
Highly-rated Soldado arrived at Spurs for £26million and with a genuine bit of buzz, but sadly the striker never managed to make a name for himself with the Lillywhite loyal.
Part of the influx of players available with the money from Gareth Bale, he smashed the club transfer record of £17million the club made earlier in the same window for Paulinho, who arguably deserves his own spot on this list.
Between 2013 and 2015 he played 52 league games for Spurs, scoring just seven goals. To make things worse, only two of the six goals he bagged in first season came from open play.
Once English football’s next big thing, he bore resemblance to David Beckham in his play style.
But it wasn’t meant to be for the man from Peterborough, managing 42 league games and three goals in five years for Spurs after signing from Blackburn.
At the age of 29, without a club and out of love with footballs, David Bently hung up his boots.
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