Make or Break at San Siro: Why Samuel Chukwueze Must Finally Own Milan’s Right Flank

By Victor Fakiya

Samuel Chukwueze arrived back at AC Milan this summer looking like a €20 million afterthought. Three years after his move from Villarreal, the Nigerian winger’s future at San Siro is entirely up in the air. A frustrating loan stint at Fulham ended with the London club declining their buy option, sending him back to Italy to face a brutal reality. He has to fight for his place all over again.

When Rúben Amorim took the reins at San Siro, Samuel Chukwueze’s Milan career looked set to fade away silently. The Portuguese tactician would have been entirely justified in deciding the winger’s time was up. Instead, Amorim saw a chance to improve him, keeping the Nigerian player and completely changing his tactics to make him play much better.

The right wing-back position in Amorim’s 3-4-2-1 setup is now occupied by Chukwueze. He had no prior experience in that position. Despite this, the Nigerian has started both Serie A matches and has an assist after only two games.

We can’t yet definitively state that Chukwueze has improved his situation at Milan. Amorim has bestowed upon him a clarity of role and managerial confidence that were largely absent during his club career.

He must now prove his capability to preserve it.

Milan Never Quite Got The Player They Bought

Chukwueze arrived at Milan in July 2023 after five years at Villarreal.

Samuel Chukwueze 2⃣1⃣
It suits you well 🤩#ACMQuest #SempreMilan pic.twitter.com/nyOyAJsBWy

— AC Milan (@acmilan) July 27, 2023

The Nigerian had built a strong reputation in Spain. He made 207 appearances for Villarreal’s first team and scored 37 goals. He also helped the club win the Europa League in 2021.

Milan saw a player with speed, skill and the ability to take on defenders. But things did not go as planned. He played a few games for the team. Milan eventually decided that a loan move made more sense.

In September 2025, he joined Fulham for the season.

England did not completely change Chukwueze’s situation, but he had some good moments.

He made 25 appearances for Fulham, scoring three goals and providing four assists. He also produced one of his best performances of the season against Manchester City.

Chukwueze came off the bench and scored twice as Fulham lost 5-4 in December 2025.

But Fulham still did not sign him permanently. The Nigerian therefore returned to Milan in the summer. This time, however, a new manager was waiting for him.

Amorim Saw A Different Way To Use Him

Amorim’s arrival changed the situation.

The Portuguese manager has moved Milan towards a 3-4-2-1 system. That system uses two centre-backs, a central defender, two wing-backs and three attacking players behind the striker.

Chukwueze has been used on the right side as one of those wing-backs. It is a new position for him.

Chukwueze has played most of his career as a winger. His job was usually to stay high, receive the ball and attack defenders.

Now he has to do more. He still needs to attack. But he also has to help Milan defend. He has to track opposing players, recover his position and help his team when it loses the ball.

Amorim knows this is a challenge. In August, the Milan manager said Chukwueze’s ability to defend would depend on his mentality and character. He also said the Nigerian had already improved in that part of his game.

“Defending is about spirit and character, which Chukwueze has. He’s improving. We think he suits the position,” Amorim said.

The manager’s point is simple. Chukwueze does not need to become a traditional defender. He needs to work hard enough to handle the defensive side of his new position. That is the biggest test of the experiment.

He Gave Amorim An Early Reason To Trust Him

Chukwueze’s first big chance to show what he could do came against Manchester United in pre-season.

Milan won 4-2 in Wrocław on 15 August. Chukwueze started at right wing-back and was involved in three of Milan’s four goals. He scored the equaliser and provided two assists.

The first two league games have provided better evidence.

Chukwueze started Milan’s opening Serie A match away to Torino. He played the full 90 minutes and created the second goal with a cross that Adrien Rabiot headed into the net. Milan won 2-1.

A week later, Chukwueze started again against Venezia and played another 90 minutes. Milan won 2-0.

After two league games, he has played 180 minutes, started twice and provided one assist.

That is already a big change from his previous seasons.

For much of his time at Milan, Chukwueze had to fight for minutes. Under Amorim, he has started the first two league games of the season. The next question is whether that continues that trajectory.

The New Position Could Suit Him

There is a reason Amorim may be willing to take this risk. Chukwueze’s biggest strengths have always been clear. He is quick, good with the ball and dangerous when he runs at defenders. He can play on either wing and deliver crosses into the box.

A wing-back role allows Milan to keep many of those qualities.

He can still receive the ball wide and attack. The difference is that he starts from deeper positions and has more space to run into.

That could be useful in Amorim’s system.

It also gives Chukwueze a chance to become more involved in games. Instead of waiting for the ball in the final third, he can help Milan move the ball from deeper areas and then join attacks.

But there is a price. He has to defend. If he loses the ball and does not recover quickly, Milan can be exposed on the right side. If he moves too far forward at the wrong time, he can leave space behind him.

This is why Amorim’s experiment will take more than a few good games to judge.

Chukwueze Also Has More Room At Milan Now

The timing of his return is important. Milan are a different team from the one Chukwueze joined in 2023.

Amorim is building the team around his own ideas. The club have also changed their attack, including the arrival of Gonçalo Ramos. Rafael Leão has also left Milan for Galatasaray in a deal reported to be worth €45 million.

Chukwueze should not be seen as Leão’s replacement. They are different players and play different roles. But Leão’s departure does mean there is more room for other attacking players to take responsibility. That could help Chukwueze.

He is no longer trying to force his way into the same team he left last season. He is now part of a new Milan team with a new manager and a different style.

That gives him another chance to prove that he belongs there.

Now Chukwueze Has To Keep Shining

There is already an example of what Amorim can do with an African winger in an unfamiliar role.

At Manchester United, Amorim used Côte d’Ivoire international Amad Diallo as a wing-back after taking over the club in November 2024. Diallo had mainly played as a winger before then. Amorim saw that his speed, ball control, and ability to run could also work from a wider, deeper position.

The change did not make Amad a defender. Instead, it allowed him to stay involved in United’s attacks while asking him to work harder without the ball. Amorim later said he liked Amad in the position because he could run and had the physical ability needed for the role.

Amad then became one of the players who benefited most from Amorim’s arrival. He went from struggling for a regular place to becoming an important player in the team. He scored, created chances and showed that he could handle the demands of playing wide in Amorim’s system.

Chukwueze now has a similar opportunity. Like Amad, he is an African winger with pace and the ability to beat defenders. And he has to prove that he can defend well enough for Amorim to keep trusting him there.

Amorim has already shown Chukwueze that he sees value in him. The Nigerian has responded with two starts, 180 minutes and an assist in Milan’s opening two league games.

Now he has to do what Amad did at Manchester United: make the manager’s idea work on the pitch.

If he can improve his defending without losing his pace, crossing and ability to take on defenders, this could become more than a short-term experiment.

It could give Chukwueze the role he has been looking for at Milan since 2023.