Ruben Amorim has been at AC Milan for barely two months and, already, that is starting to sound an awful lot like Manchester United.

A 2-0 home defeat to Benfica in the Europa League on Wednesday brought boos from the San Siro and some remarkably strong criticism in Italy.

It wasn’t just the result of course. Milan looked lost, and Amorim’s words before and after the game haven’t helped him.

La Gazzetta dello Sport say the “alarm is serious”. In a separate piece, they describe “shadows looming over Amorim’s management” and declare a “red (black) alert”.

Anything looking familiar so far?

Amorim is already talking about failure

One of the most striking parts is how Amorim himself is (still) talking.

“If I have to fail, it’s better that I fail big,” he said around the Benfica game. His point was that, if things go wrong, he wants them to go wrong while sticking to his ideas.

That immediately caught Gazzetta’s attention. They explicitly compare the situation to Manchester United, where Amorim once made it clear he wouldn’t change his system ‘even if the Pope asked him to’.

There’s one rather important difference: those conversations came much later in his Manchester United spell. At Milan, he’s been there a matter of weeks. And there’s more.

“I want to help this club, I don’t know if I’ll have the necessary time, but the players listen to me a lot in training and that gives me hope,” Amorim said.

Again, it’s quite something to hear so early. He is coming across as increasingly uneasy and almost fatalistic about what could happen.

From a “10/10” transfer window to the wrong squad

Ruben Amorim
Milan, Italy. 28 August 2026. San Siro Stadium. Enilive Italian Serie A football Championship. AC Milan VS Venezia FC. Players of Milan during warmup. Ruben Amorim, coach Milan. – Editorial credit: Cristiano Barni

There’s another déjà vu: Amorim said Milan’s squad isn’t entirely suited to his football.

“If the squad is poorly suited to my game? Partly, yes. I don’t have the perfect characteristics because it’s impossible to arrive at a new club and have everything ready.”

Fair enough in isolation. Except around ten days earlier Amorim had rated Milan’s transfer window “10 out of 10”.

That’s the contradiction now being picked apart in Italy. Gerry Cardinale had worked closely with Amorim over recruitment and made a real effort to support his new manager.

Both things can’t be true. Either Milan had a 10/10 window or Amorim has helped pick a squad which doesn’t properly suit his football.

Italian media already questioning his decisions

Ruben Amorim sat in dug out

Calciomercato have gone further and argue Amorim is currently adding to Milan’s problems instead of solving them. They question his constant changes to the starting XI.

Five players were changed for Benfica, despite Milan already being five competitive matches into the season. The criticism is simple: how can automatic patterns develop when the team keeps changing?

The outlet says Amorim is getting his starting teams wrong, overestimating squad players and then trying to repair things with half-time substitutions.

There’s even an uncomfortable comparison with Marco Silva. Because the former Fulham boss also arrived at Benfica this summer. Yet, according to Calciomercato, his team already look like they’ve been playing together for years. Amorim’s Milan still look like a work in progress.

The last three performances against Juventus, Lazio and Benfica have now caused enough concern for the ownership to get involved.

Cardinale wants answers

Gazzetta image
‘Nightmare in Milan’ -‘Whistles at San Siro’ – Ruben Amorim rated 4/10

Cardinale, Giorgio Calvelli and Amorim are expected to hold talks to assess what’s going wrong. The Milan owner is particularly disappointed with those last three performances.

He also wants Amorim to explain both the problems he publicly listed after Benfica and his comments about the squad.

For now, there’s an important distinction to make: Amorim still has Cardinale’s full backing. Nobody is saying he’s about to be sacked.

But the message in Italy is already becoming pretty clear. Milan need wins, Amorim needs to settle on a team, and some of the noise surrounding him is sounding remarkably similar to Manchester.

After leaving Manchester United, Amorim said he’d learned from the experience and was certain he’d become a better manager. But two months into the Milan job, Italy is already asking some of the same questions.

What Fabio Capello has said

Vastly successful as a manager, including four Serie A titles and a Champions League at AC Milan, Fabio Capello isn’t liking what he’s hearing or seeing from Ruben Amorim.

The 80-year-old has offered some advice: “Why, instead of focusing on attack, don’t you focus on defence, which is leaking everywhere?

I have an old maxim that I always repeat: you have to know how to make wine from the grapes you have available. Depending on the quality of the grapes you have, make the appropriate wine. But if you always want to make champagne, but the grapes you have aren’t suitable for that, the result will be as we saw.”