Tottenham chairman Daniel Levy is still looking to bolster Spurs' attacking ranks before the transfer deadline in four days' time, and given their previous luck this window, it wouldn't be surprising to see them scrambling till the eleventh hour.
Thomas Frank watched on as his side failed to secure the signings of Morgan Gibbs-White and Eberechi Eze, both in spectacular fashion.
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Gibbs-White saw his once-advanced move to N17 blocked by Nottingham Forest, who wrote a letter to Spurs threatening legal action, as weeks of back and forth between the clubs ensued before the 25-year-old signed a new contract regardless.
Meanwhile, Tottenham were convinced they'd land Eze at one stage - having agreed personal terms with the player and the finances of a deal with Crystal Palace - only for Arsenal to swoop in and hijack the transfer.
Their need for a number 10 is glaring, having lost both Dejan Kulusevski to a knee injury earlier this year and James Maddison to an ACL rupture in pre-season.
FFC Spurs - James Maddison
FFC Spurs - James Maddison
At one point, Frank was planning to head into 25/26 with a fully fit Maddison and Gibbs-White, only to now have neither. In an ideal world, it's been reported that the Dane would like two new playmakers (Gary Jacob), but that scenario looks near-impossible barring a last-gasp miracle.
In terms of who they could bring in, Spurs are in the market for a new centre-back, number 10 and a winger.
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One of the playmakers on their radar is West Ham United's Lucas Paqueta, and the Hammers are reportedly open to selling, if their asking price is met, and they can source a replacement (Paul O'Keefe).
The Brazil international would be Spurs' second signing of the window from their London rivals after a £55m deal for Mohammed Kudus, which also ended an unofficial transfer embargo between the two clubs spanning 14 years.
Tottenham offered Yves Bissouma in swap deal for Lucas Paqueta
According to TBR Football and journalist Graeme Bailey, Levy and the Spurs recruitment team actually made a unique proposal for Paqueta recently, involving Galatasaray-linked Yves Bissouma.
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Bailey reports that Tottenham offered Bissouma in a direct swap deal for the Brazil international, and the talks centered around Paqueta going the other way on a straight loan.
Bissouma also would've departed for the London Stadium on a dry temporary deal, but it is believed that negotiations didn't progress to the final details and the Mali international has now agreed to join Galatasaray instead.
According to other reports, West Ham want £60 million to part company with Paqueta, so Spurs will need to head back to the negotiating table.
“He drives me mad sometimes but everybody who watched him would have said: ‘This player has got incredible talent’," said former West Ham boss David Moyes in 2023.
“There is a word that goes around, a maverick. He is that for us. It is really important we get him in and adapt to him and accept some of his things.
“He may not do things which are what I would say conventional, but we are really enjoying him at the moment, and he is terrific at taking the ball under pressure. But also there are moments when I say: ‘What are you doing?’”