Pervis Estupiñán Tottenham transfer interest grows as De Zerbi targets reunion

Pervis Estupiñán’s difficult season at AC Milan could be heading towards an early conclusion, with Tottenham now emerging as a realistic destination if the defender leaves Italy this summer.

The Ecuador international only joined Milan from Brighton last year, but his place in the squad has weakened significantly in recent months, raising serious doubts over his long-term future at San Siro.

According to reports in Italy, Tottenham manager Roberto De Zerbi is interested in reuniting with the left-back after their successful spell together at Brighton.

That possibility is now gaining momentum.

Expectations were high when Milan signed Estupiñán.

His attacking energy and Premier League experience appeared to make him a natural fit for Serie A, particularly in a system that values aggressive full-backs.

But things have not developed as expected.

Instead, academy defender Davide Bartesaghi has overtaken him in the pecking order, including in key matches.

That was underlined again during Milan’s recent goalless draw against Juventus, where Bartesaghi got the nod despite strong suggestions Estupiñán would start.

When Estupiñán entered at half-time, he struggled to change the game.

That performance only strengthened the feeling that his Milan future is fading.

De Zerbi knows Estupiñán well.

Their partnership at Brighton brought some of the defender’s best football, particularly in attacking phases where his overlapping runs and crossing became major weapons.

That familiarity matters.

At Tottenham, De Zerbi’s tactical demands would suit Estupiñán’s strengths far more naturally than his current role in Milan.

From the last few weeks of Milan’s campaign, it has become increasingly clear that Max Allegri does not fully trust him as a consistent starter.

That changes the transfer landscape.

If Tottenham move early, they may find a deal available at close to Milan’s original €17 million investment.

That price would represent relatively low risk in the current market.

Tottenham’s interest in Liverpool defender Andy Robertson has also been widely reported, and that creates an interesting choice.

Robertson offers experience and leadership, while Estupiñán offers younger legs and familiarity with De Zerbi’s demands.

The financial difference could be significant.

Robertson could arrive without a transfer fee, while Estupiñán would require an agreed deal with Milan.

That may shape Tottenham’s thinking.

Having followed De Zerbi’s teams closely in England, full-backs are often central to his attacking patterns. That makes Estupiñán a logical fit if Spurs prioritise system compatibility over pure market value.

Still, no final decision appears close.

Tottenham’s summer recruitment plans are expected to become clearer once the season ends, with left-back reinforcement high on the agenda. Estupiñán’s future at Milan will likely depend on whether he can force his way back into the starting side over the final weeks.

If his role remains limited, a return to the Premier League looks increasingly realistic.

This is one transfer story that could develop quickly.

Would Estupiñán be the right fit for Tottenham, or should Spurs go for experience with Robertson?