The Estupinan conundrum: Why Amorim might have delayed sale to Aston Villa

It looked as though Pervis Estupinan’s time at AC Milan was coming to an end after just one year, but now things have been thrust into doubt.

Reports over the past 10 days or so have suggested that Aston Villa advanced rapidly in talks with Estupinan, even agreeing personal terms over a move back to the Premier League. The fee was not expected to be an issue either, especially after their big-money sales.

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Several sources spoke of the deal being at an ‘advanced stage’, but that was a few days ago now. The reliable Matteo Moretto said the completion was ‘one step away’ back on July 18. At the time of writing, on July 23, that final step has not yet come.

Instead, reports in Italy are now claiming that the new head coach Ruben Amorim has asked the Milan management to pump the brakes on the sale. It seems like an odd U-turn, given Estupinan had a difficult first season in Italy and appeared so keen to reunite with Unai Emery.

What is it that made Emery want to work with the Ecuadorian again after their time together at Villarreal? By extension, what is it that Amorim might have seen in Estupinan that makes him want another look? Rohit Rajeev has put forward some ideas.

A case for Estupinan

There could be a tactical reason that Amorim wishes to evaluate Estupinan up close, one that fits perfectly with his system.

As shown on the board, Milan under Amorim are expected to build in a 3-2-5 structure when in possession.

The back three provide the foundation, the double pivot controls the centre, while the front five stretch the opposition both horizontally and vertically.

This positional structure is key to understanding why Amorim values certain player profiles, and why Estupiñán could have a role to play.

With Estupiñán comfortable inverting into central areas, Milan could gain an extra tactical dimension.

As Estupiñán moves into the left half-space, Pulisic is free to drift wide and occupy the touchline, stretching the opposition horizontally.

Crucially, Milan don’t lose presence between the lines because Estupiñán fills the vacated half-space. This maintains Amorim’s positional structure while creating better spacing and more passing options in possession.

🔄 With Estupiñán comfortable inverting into central areas, Milan could gain an extra tactical dimension.

➡️ As Estupiñán moves into the left half-space, Pulisic is free to drift wide and occupy the touchline, stretching the opposition horizontally.

⚙️ Crucially, Milan don’t… pic.twitter.com/xkJd9zIM4u

— Rohit Rajeev (@keralista) July 23, 2026

We’ve seen this before. Under Roberto De Zerbi at Brighton, Pervis Estupiñán and Kaoru Mitoma constantly rotated positions, with Estupiñán inverting into central areas while Mitoma held the width, before switching again.

That fluidity made Brighton far less predictable and constantly forced opponents to adjust their defensive shape.

Amorim could recreate a similar dynamic at Milan, with Estupiñán and Pulisic interchanging to create overloads while maintaining the team’s positional structure.

🔄 We’ve seen this before.

Under Roberto De Zerbi at Brighton, Pervis Estupiñán and Kaoru Mitoma constantly rotated positions, with Estupiñán inverting into central areas while Mitoma held the width, before switching again. pic.twitter.com/TEkHzhes5Z

— Rohit Rajeev (@keralista) July 23, 2026

Benefits and concerns

The benefit? Serie A is heavily influenced by man-oriented defending. Paulo Fonseca once spoke about how he was more worried about facing Cagliari just days after beating Real Madrid 3-1 in the Santiago Bernabeu, partly because of the man-to-man approach.

Constant positional rotations and fluidity make it much harder for defenders to maintain their assignments, creating gaps that can be exploited through movement and quick combinations.

The problem? While Estupiñán may offer this tactical flexibility, his individual performances have not always been convincing and he has made errors leading to goals. An example? He scored the derby decider vs. Inter, then one week later allowed Gustav Isaksen in behind to net Lazio’s winner.

That is why, despite the tactical upside, Milan could still decide that selling him is the better long-term solution if a stronger profile becomes available.

From a data standpoint (thanks to DataMB for the player comparison tool), there are some rather striking metrics too.

When plotting where Estupinan ranks against the existing options in Alexis Saelemaekers and Davide Bartesaghi, plus previous wing-backs Amorim has relied upon such as Geny Catamo, Geovany Quenda and Amad Diallo, it is instantly evident that the former Brighton man offers something a bit different.

Of the other names listed, none really come close to matching what Estupinan did on the defensive end during his final season with the Seagulls (greater sample size than last season at Milan). However, this came at the expense of attacking creativity compared to his peers.

As we established in our three-part tactical analysis on Amorim’s system, he likes to have a balance on the flanks. They are arguably the most important players in a his 3-4-2-1 formation.

More than just wide defenders, they are crucial to maintaining the team’s structure in both possession and out of possession, often determining the balance of the entire formation.

His tactical approach relies heavily on the wing-backs to provide width, support progression, and contribute in the final third, while also dropping back quickly to form a back five when defending.

Typically, the two wing-back roles are not identical. On one side, Amorim often prefers a more explosive profile: a player with strong dribbling ability, high work rate, and the capacity to consistently win 1v1 duels and carry the ball forward.

On the opposite flank, the role can be more playmaking-oriented. Rather than relying on dribbling, this wing-back is often expected to contribute through passing, combination play, and intelligent positioning to help circulate possession and create attacking connections.

Whether Estupinan could be the perfect complement to a more attack-minded wing-back is probably what the coach wants to discover. It remains possible that he might then agree the sale. Who the replacement might be is unknown, but at least Amorim can glean a better idea of what he wants.