Tottenham are one of the sides showing an interest in AC Milan left-back Pervis Estupinan, who has previously worked under new manager Roberto De Zerbi, according to a report from Milan Live.
Spurs recently confirmed the appointment of De Zerbi on a five-year deal, with his first task being to keep them in the Premier League after a dismal season.
Focus will then quickly shift to the transfer market, as there's no doubt they'll need to bring in a host of new additions if they want to avoid enduring another difficult campaign.
Whether Tottenham can avoid the drop remains to be seen, but it's going to be an interesting summer transfer window for the north London club, whatever happens.
If Tottenham remain in the Premier League, Spurs are likely to be busy in the market, and there's no doubt De Zerbi will be demanding plenty of signings.
Tottenham Eyeing Former De Zerbi Star
According to a report from Milan Live, left-back Estupinan looks set to leave Milan in the summer transfer window, and there's a chance he could end up at Tottenham.
Spurs are interested in Estupinan, who previously worked under De Zerbi at Brighton, and the new Tottenham manager is believed to be a strong admirer himself.
The report confirms that he will be leaving this summer, with his representatives now exploring new opportunities ahead of the 2026/2027 campaign.
Estupinan, who De Zerbi thinks can be 'one of the best in the world', hasn't been a regular for Milan this season, starting just 12 Serie A games, playing a total of 888 minutes.
The Ecuadorian international enjoyed some of the best football of his career under De Zerbi, producing 16 goals and assists combined in 64 matches. Estupinan has also only played under Unai Emery more than De Zerbi, so the Tottenham manager knows him better than most.
Tottenham Could Eye New Left-Back
With Ben Davies being out of contract at the end of the season, Spurs could look to bring in a new left-back in the summer transfer window ahead of the 2026/2027 season.
Souza was brought to the club back in January, but the young Brazilian is at the beginning of his career and is not quite ready to be playing in the Premier League every single week.
If Spurs remain in the Premier League, they'll likely want to bring in reinforcements all over the pitch, so it's certainly plausible that a new left-back could arrive during the summer transfer window.