The blockbuster Tottenham swap deal involving a former manager that could define the January window

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Tottenham are pushing to strengthen their defensive options before the window closes - could a rare swap deal help them out?

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Cristian Romero's last-gasp header rescued a 2-2 draw, rescued Thomas Frank’s blushes and saved Tottenham Hotspur from an embarrassing defeat against the division’s second lowest-ranked club. However, the full-time whistle at Turf Moor and the last-minute equaliser didn’t save Frank and his team from being booed off the pitch by the away end as the pressure intensified on the Dane, with Spurs having now won just two of their last 14 league games.

As it stands, Spurs are in 14th position, Frank is battling to save his job and the problems that have haunted the capital club since the end of Ange Postecoglou’s tenure continue to damage the club’s chances of finishing in the upper echelons of the league table. But can they improve matters before the end of the January transfer window?

Tottenham hope to sign defender before the window closes

Spurs remain winless in the Premier League in 2026 despite an encouraging display against Borussia Dortmund in the Champions League, and they’ve failed to control games - and have at times switched off defensively, particularly from set plays despite both Romero and Micky Van de Ven’s habit of netting at the other end of the pitch.

Calciomercato understands they are in the market for a central defender to help sort things out at the back, and have turned their attention back to a star that has been on their radar since last season when Postecoglou was still in charge.

The outlet explains Spurs are keen on signing Alessandro Buongiorno from Napoli. The 12-time Italian international has played in Naples since 2024 when he left Torino and formed part of the club’s Serie A title winning side last season. Overall, he’s played 49 matches for Napoli and has looked extremely solid, earning himself a place in the Serie A Team of the Season last year.

The blockbuster Spurs and Napoli swap deal which could define the winter window

Buongiorno has the ability to be a strong addition to the Tottenham team, but he’s under contract with Napoli until 2029 and is unlikely to depart for a cheap figure given that he’s a regular for the club. However, his Napoli side are in fourth position and unlikely to challenge for the title this season while they are also at risk of dropping out of the Champions League unless results go in their favour in the last game. Tottenham, who are on course to stay in Europe a little while longer, could use this to their advantage as they aim to once again go to the latter stages of an elite competition.

One way Tottenham could look to entice Buongiorno to North London is by striking a deal with their former manager and perhaps giving him a player that he wants in exchange for the defender as a sweetener. A viable option for this sort of deal could potentially be out-of-favour defender Radu Dragusin, formerly of Genoa, who is reported to be the subject of strong interest from clubs in Italy - including Conte’s Napoli - despite his injury-hit spell in North London.

Il Corriere dello Sport in Italy understands AS Roma have already tabled a loan move but add that Conte’s side are also interested. With Dragusin thought to be unsettled in North London and perhaps surplus to requirements it could make sense to try and include him in negotiations to cut down the overall figure and fill a void in both manager’s squads.

It looks to have worked for Aston Villa in their pursuit of Tammy Abraham, with Yasin Ozcan going in the opposite direction, and could be something we see from more top-flight clubs moving forward, particularly if it helps from a PSR point of view. Perhaps Spurs could repeat the trick, especially as their need for defensive reinforcements has been sharpened by the apparent failure of their reported bid for Andrew Robertson.