The January transfer window is undoubtedly a tricky time for Milan as they need to do their best to ensure that this month's trade does not spoil their challenge to the title. The Rossoneri certainly have a lot of players who can challenge for the Serie A title, but if the club is not careful, these players may leave in the winter window. One of those players is centre-back Romagnoli, who was once considered the cornerstone of San Siro's revival but may now be tempted to leave the club and embark on a new adventure. Although Roma Jr. was a left-back in his youth, he has now become a centre-back who can play in a three-back or four-back system.
After a brief break at Roma, Romagnoli was sold to Milan for 25 million euros and signed off on a five-year contract, while including a 30% revenue share clause for a future transfer that would be paid to Roma if he was eventually sold. Over the past six seasons, Romagnoli has made more than 230 appearances for the club and has become one of the most accomplished centre-backs for the Italian international and Serie A.
Unlike traditional Italian centre-backs, Romagnoli is an elegant, composed left-footed defender who likes to use his technical skills to move around the pitch and complete tasks in the heart of his own penalty area. As a result, the centre-back has been highly regarded in Italian football for some time. In 2015, former Milan coach Mikhailovic said that "Romagnoli has everything to become the new Nesta", while Italian football star Di Biagio went a step further: "Technically, Romagnoli may even be better than the 20-year-old Nesta." But since then, Romagnoli has not achieved what Nesta has achieved, although given his 26-year-old age, the defender still has plenty of time to reach his potential.
Although it is now his seventh season at Milan, Romagnoli's future at the club is uncertain due to the circumstances of his contract. According to Italian transfer expert Di Marzio, Milan have offered the defender a new contract, but there has been no progress as his new contract is paid less than his current contract at the club. As a result, Romagnoli may be looking for a new club and it is Tottenham from the Premier League who is watching him closely for the moment. According to British reports, Tottenham's new head coach Antonio Antonio Conte has made it clear that he wants North London clubs to bring his compatriots to the Premier League as soon as possible. That means the January transfer window could open a new door for the former Milan captain.