Tottenham hand ‘last man standing’ a transfer ultimatum, as situation threatens to turn sour

Tottenham have handed Sergio Reguilon – the sole remaining player they aim to offload – a transfer ultimatum amid an important deadline now being less than a week away, according to multiple reports.

Tottenham successfully rid their books of numerous unwanted stars over the summer. Among the first-team stars to depart in various guises were Eric Dier, Ivan Perisic, Ryan Sessegnon, Japhet Tanganga, Joe Rodon, Emerson Royal, Tanguy Ndombele, Oliver Skipp, Pierre-Emile Hojbjerg, Giovani Lo Celso, Manor Solomon, Bryan Gil, Alejo Veliz, Troy Parrott and Dane Scarlett.

Exit opportunities were also sought for left-back Sergio Reguilon who does not feature in Ange Postecoglou’s plans.

Explaining why, the Athletic – who labelled Reguilon the ‘last man standing in Tottenham’s outcasts’ – recently stressed Postecoglou favours full-backs who maraud inside and become heavily involved in the build-up play.

By contrast, Reguilon is a full-back whose game is built around overlapping his left winger and firing crosses into the box.

In essence, Reguilon’s plight closely matches what has happened with Ben Chilwell under Enzo Maresca at Chelsea. Their greatest strength going forward is not a trait their managers value highly.

Tottenham partly to blame for Reguilon being stranded

But despite Tottenham making it clear Reguilon was up for grabs, a move did not materialise. Reporter Ben Jacobs subsequently claimed the blame partly lays with Spurs.

Indeed, he explained Tottenham pushed for a Reguilon to leave either in a permanent deal or in loan deal that contained an obligation to buy.

Unfortunately for Spurs, the bulk of interest in Reguilon only centred around loan moves and no club was willing to include an obligation to buy.

As such, Reguilon has remained in north London where his outlook for the current campaign is exceedingly bleak.

Along with fellow full-back Djed Spence, Reguilon was recently omitted from Tottenham’s squad for the group phase of the Europa League.

Reguilon is in the final year of his Tottenham contract and according to several fresh updates, Spurs have set their sights on offloading Reguilon to Turkey.

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Turkey or bust for unwanted Reguilon

The Turkish transfer window (closing on September 13) is one of very few that still remain open. Fenerbahce – now managed by Jose Mourinho – have been linked with a late move for either Reguilon or Chilwell.

Per the latest from Football Insider, Reguilon has been given a ‘Turkish ultimatum’ by Spurs.

In other words, he’s been informed if he doesn’t join a Turkish club he’ll spend the next four months in limbo until the January window opens.

The obvious question to ask is if Tottenham don’t find a buyer, why not just use Reguilon as back-up to Destiny Udogie and Ben Davies?

On that front, Postecoglou has already hinted Reguilon might not be reintegrated into the first-team set-up even if he remains in north London.

When speaking about Lo Celso and Reguilon (prior to Lo Celso’s re-signing with Real Betis), Postecoglou said the pair “don’t have to get integrated back into the squad” if they failed to secure moves away.

He continued: “It’s pretty clear where they sit in terms of where we are as a squad and where we are as a team.

“But I’ve never been one to force people out. They’ve got decisions (to make) about their own careers and what they want to do.

“And if they’re still here, they’re still here. We’ll work around that scenario. But it certainly won’t affect the way we work in the first team.”

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Spurs could accept unfavourable terms to avoid situation souring

The lack of viable exit destinations now means Tottenham may be forced into accepting less-than-ideal terms for a player in the final year of his contract.

To facilitate an exit, Spurs may have to accept a loan that does not contain an option or obligation to buy.

Such a move would mean Tottenham don’t generate a transfer fee as Reguilon would become a free agent when the loan ends, but it would net them a saving on wages.

It would also remove from the picture a player who Postecoglou has zero intention of using and who according to the Athletic, can be a problem in the dressing room if things aren’t going his way.

Indeed, their report stated ‘there is an internal perception at Tottenham that when things aren’t going well or Reguilon is not being selected to play, he is not the easiest character.’

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