Between Dreams & Reality – Are Milan Right to Pursue Ex Man Utd Boss? | OneFootball

Even without the distraction of European football, Massimiliano Allegri failed to steer AC Milan back to the UEFA Champions League on his return to San Siro in 2025/26.

A heartbreaking home loss to perennial strugglers Cagliari on the final weekend condemned the Rossoneri to a gut-wrenching fifth-place finish, with Como leapfrogging them into fourth right at the death.

It didn’t take long before the dominoes started to fall. First to feel the wrath of Paolo Scaroni and Zlatan Ibrahimovic was none other than Max Allegri. The club relieved him of his duties immediately after the end of the season.

Desperate to fill the gap before the beginning of the 2026 FIFA World Cup, the 19-time Serie A champions were quick to identify Oliver Glasner as a top candidate to replace the Italian veteran.

Fresh off leading Crystal Palace to UEFA Conference League glory, Glasner entered the free-agent pool, having announced his departure from Selhurst Park at the end of a history-defining campaign.

In addition to the German tactician, Milan had also earmarked Andoni Iraola and Antonio Conte as Allegri’s potential successors before realizing they were not realistic targets.

Glasner’s name has slowly faded away, opening the door for a surprise appointment as the Rossoneri intensify their search for a fresh direction.

Former Manchester United manager emerges on Milan’s shortlist

Ruben Amorim faltered at Old Trafford. Despite being initially perceived as a potential Manchester United savior after Erik ten Hag’s dreadful tenure, the 41-year-old crumbled under the pressure.

Brought in to replace the Dutch coach after a superb four-year stint at Sporting CP, Amorim was tasked with turning the Red Devils’ fortunes around. However, he failed to meet expectations.

Instead of being part of the solution, he became part of the problem.

With a miserable 38% win rate, he left the club with the lowest win percentage of any permanent Man Utd boss in the post-Sir Alex Ferguson era, casting major doubt on his managerial credentials.

Since being sacked by United in January, no one was even considering appointing Amorim until now. Desperate times call for desperate measures, and Milan seem willing to take this gamble.

According to several news outlets around Europe, the San Siro giants have opened talks with the Portuguese manager over the vacant job, with Amorim reportedly ready to take one of the hottest seats in European football.

Recipe for disaster or win-win deal?

Milan have hit rock bottom. Two consecutive seasons without Champions League football, and they’re preparing for a summer of upheaval, with several standout stars, including Rafael Leao, set to wave goodbye to the club.

Having missed out on the Champions League prize money, the Rossoneri are likely to operate on a tight budget this summer, so raising funds through player sales could be their best chance to build a competitive squad again.

The picture looks bleak, and even the most optimistic Milan fans do not expect the seven-time European champions to challenge for the Scudetto next season. With that in mind, they’d be wise to pursue a wartime manager.

However, they appear to have other plans. Seemingly unfazed by Amorim’s disappointing tenure at Old Trafford, the Rossoneri are ready to bring the Portuguese tactician to San Siro ahead of a transitional summer.

Whether it’s an act of desperation or a masterstroke waiting to happen remains to be seen, but one thing is certain – Milan cannot afford another mistake of this magnitude.

Amorim’s attacking philosophy and track record of developing young players may offer reasons for cautious optimism, yet recent events at Old Trafford suggest this appointment would carry considerable risk.

With expectations at San Siro permanently sky-high and patience running thin, Amorim would walk into a baptism of fire from day one. And perhaps, this is precisely what he needs to get back on track.

Final verdict

Amorim’s success in Lisbon made him one of Europe’s most exciting young coaches. However, his first foray into Europe’s top-five leagues left a lot to be desired, and in all fairness, the Milan job isn’t much different from what awaited him at Man United.

A fallen giant under pressure to return to the top, limited margin for error, and supporters desperate for immediate results – the similarities are difficult to ignore. His arrival could be just what both Amorim and Milan need to rediscover their identity and prove their recent setbacks do not define them.

Then again, there’s an equally realistic chance this ends up becoming another case of the right manager arriving at the wrong club at the wrong time.

Nevertheless, Glasner feels a genuinely better fit.