The transfer market is often a place of second chances, and for Pervis Estupinan, a move to North London might be exactly what he needs to revive a stalling career.
After making a high-profile move from Brighton to AC Milan last summer, the Ecuadorian left-back has found life in Italy much more difficult than many expected. However, recent reports suggest that Tottenham Hotspur is keeping a very close eye on the situation, and the path to bringing him back to the Premier League appears surprisingly clear.
Estupinan’s time at the San Siro has been a struggle of consistency and tactical fit. So far this season, he has managed only sixteen appearances in Serie A, accumulating fewer than one thousand minutes on the pitch. For a player who was once considered one of the most dynamic full-backs in England, these numbers are a stark indicator of his current standing.
At times, the Milan coaching staff has even preferred young Davide Bartesaghi over the experienced South American, suggesting that trust in Estupinan’s defensive reliability has hit a low point. The issues in Italy seem to stem from a lack of defensive discipline.
While he scored a significant goal against Inter Milan recently, that moment proved to be a bit of a false dawn. Almost immediately after that high point, a major defensive lapse against Lazio reminded everyone why he has struggled to hold down a permanent spot in the starting eleven. In a league that prizes tactical rigidity and defensive awareness, Estupinan has looked like a square peg in a round hole.
Despite these struggles, Tottenham remains interested. Initial inquiries have reportedly been made, but there is a major caveat to any potential deal. Most insiders believe that a move for Estupinan is directly tied to the potential appointment of Roberto De Zerbi. The Italian manager, who worked with Estupinan at Brighton, is currently one of the leading candidates to take the permanent job at Spurs.
If De Zerbi arrives, it is highly likely he will want to bring in players who already understand his complex and demanding system. The terms for a potential transfer have now become clearer. AC Milan is not inherently opposed to letting the left-back go, as they have been largely disappointed by his output.
Their main goal is to ensure they do not suffer a significant financial loss on the investment they made just a year ago. Last summer, the Italian giants paid roughly €17 million plus bonuses for his services. According to reports from Calciomercato, Milan would be willing to sanction a sale for around €14 million. This figure would allow them to balance their books and reinvest the funds into a replacement who better fits their current style of play. For a club with Tottenham’s resources, a €14 million fee is relatively modest, especially for a player with proven Premier League experience.
It represents a low-risk, high-reward opportunity, provided they have the right manager in place to utilize him. The current tactical setup at Milan under Max Allegri is notoriously pragmatic and defensive. Estupinan, by contrast, is a player who thrives when he is allowed to bomb forward and join the attack. In a restrictive system, his defensive flaws are magnified, but in an expansive system like De Zerbi’s, his offensive contributions often outweigh his mistakes at the back.
This is why the priority for Tottenham must remain the managerial hunt. While the prospect of signing a talented full-back for a bargain price is tempting, it only makes sense if the new manager actually wants him. De Zerbi is known for being incredibly specific about the types of players he needs for his system to function correctly. He demands full-backs who can act as playmakers and overlap with intensity. Estupinan fits that mold perfectly, having played some of the best football of his career under the Italian’s guidance at Brighton.
If Spurs can secure De Zerbi, the signing of Estupinan becomes a logical next step in building a project that aligns with a clear vision. It would be a “plug-and-play” signing that helps the manager implement his ideas much faster. However, if Tottenham moves for a different type of manager, one who prioritizes defensive solidity above all else, then pursuing Estupinan might just be repeating the same mistake Milan made.
As it stands, the ball is in Tottenham’s court. The price tag is set, and the player’s current club is ready to talk. The coming weeks will be decisive, not just for the club’s league status, but for their ability to attract the right leaders to the dugout. If the pieces fall into place, Pervis Estupinan could find himself back in London, playing the kind of football that made him a star, under a manager who knows exactly how to get the best out of him.
For €14 million, it is a deal that seems almost too simple for Spurs to ignore.
