New Tottenham head coach Roberto De Zerbi is eyeing a reunion with a former Brighton star.
Tottenham Hotspur have started planning for the summer transfer window after hiring Roberto De Zerbi as their permanent head coach earlier this week.
Addressing the defensive problems has to be one of the priorities heading into the summer transfer window. Amid the uncertain futures of Cristian Romero and Micky van de Ven, the club bosses must look to get in a quality centre-back. AS Roma star Evan Ndicka has emerged as a target for the North Londoners.
There is also the requirement of a new left-back, despite the signing of Souza from Santos in the winter transfer window. This is because Tottenham need a reliable starting left-back, which Destiny Udogie hasn’t proven to be in the last couple of seasons. Persistent injury problems and inconsistency have prevented Udogie from hitting the heights he was expected from the fans, resulting in Djed Spence deputising at left-back for the majority of his game time.
With De Zerbi on board now, it looks like he has set his sights on a player he knows well.
Tottenham get greenlight to sign AC Milan defender
According to a report from Milan Live, De Zerbi is ‘ready to welcome’ AC Milan left-back Pervis Estupinan to Tottenham in the summer. He is ‘appreciated’ by the new Spurs head coach, who played a key role in his emergence at Brighton and Hove Albion.
Pervis Estupinan made a name for himself in the Premier League at Brighton, for whom he provided 19 goal contributions in 104 games. This led to a transfer to AC Milan in the summer of 2025; however, the 28-year-old has struggled to adapt to life in Serie A. The Ecuadorian international has been limited to just 19 appearances at AC Milan after making some high-profile errors, yet he continues to get traction from the Premier League.
West Ham and Fulham are interested in the flying left-back/wing-back, while Spanish side Atletico Madrid are also keeping tabs. The report adds that Estupinan will leave Milan after just one season, and a return to the Premier League looks a strong possibility.
Before De Zerbi’s appointment, Tottenham made ‘simple enquiries’ about the AC Milan flop. Now with De Zerbi at the club’s helm, Spurs should enjoy an edge over other clubs in the race to sign Estupinan, who played the best bit of football of his career in the Premier League.
Estupinan would be a strong fit in De Zerbi’s system at Tottenham
Firstly, Estupinan has proven his quality in the Premier League across three seasons with Brighton, and as well as making over 80 appearances, he has experience of playing in Europe.
The other attraction of the Ecuadorian is his familiarity with De Zerbi’s possession-based system. He was one of the first names on the Italian’s teamsheet during their time together at Brighton, adding energy, pace and dynamism to the side. Blessed with a great engine, the 28-year-old could make an impact at both ends of the pitch at the Amex Stadium, and Spurs could do with him at left-back.
However, like Udogie, Estupinan’s fitness remains a concern, with the former Watford man having had muscle-related issues in the last few seasons. Hopefully, this doesn’t emerge as a red flag for the Tottenham chiefs to end their pursuit of the Milan left-back. Of course, any potential deal will likely depend on Spurs preserving their Premier League status, with a transfer for Estupinan unlikely should the club drop to the Championship.