As Tottenham prepare for a pivotal summer window, regardless of which division they find themselves in, the club will need to be shrewd in the transfer market, and Pervis Estupinan could prove a valuable addition.
Estupinan has managed just 946 minutes of league football this season—a disappointing return for a player once regarded as one of the most dynamic left-backs in Europe. The move to Italy, which cost Milan £17 million, has simply not worked out.
The most compelling argument for this deal is not the bargain price or underutilised potential—it is the De Zerbi factor.
That kind of endorsement carries genuine weight when it comes from a coach already trusted with rebuilding an entire club.
The need at left-back is pressing. First-choice Destiny Udogie continues to struggle with injury, with Djed Spence—a natural right-back—forced to deputise on several occasions. Ben Davies is also set to depart this summer, leaving the flank dangerously undermanned in that department.
However, the main caution is one of priority. Goalkeeping remains a question mark, the absence of a reliable defensive midfielder continues to leave Spurs exposed, and there are deficiencies in attack.
That said, at a reported asking price of around £13 million, Estupinan represents the kind of smart, experience-driven business De Zerbi’s Tottenham must pursue.
Reuniting a proven Premier League performer with the manager who unlocked his best football is not sentiment; it is strategy.