The ball is rolling [Newsletter]

Jun 17, 2026

🤔 Third time’s the charm?

Ruben Amorim is the new head coach of Milan. After a casting process that took about three weeks, as opposed to the 7-10 days that Gerry Cardinale first spoke about, the Rossoneri finally have someone in place. You’d think that it would be a relief for the fans after such a long wait, but just as the casting process was criticised, the outcome has certainly been so too.

Having decided to move on from Oliver Glasner, who is considered a great manager after winning three trophies with Crystal Palace, Milan travelled to the other end of that spectrum. After all, while Amorim did impress during his four and a half years at Sporting, it was a disaster at Man Utd with just 1.43 points clinched per game on average.

Now, whether that was the result of the Old Trafford side being a tire-fire of sorts is what we will have to find out during the upcoming season. But hey, maybe third time’s the charm? Amorim will actually be Milan’s third Portuguese head coach in just two years, having entrusted the gig to Paulo Fonseca and Sergio Conceicao too. God knows why the Rossoneri have that preference to begin with.

🏀 NBA causes anger

A few days ago, when talking about Milan’s casting process, Matteo Moretto explained that they want an ‘NBA-style’ organisation and that the CEO, Head of Football, and head coach roles are not ‘necessarily connected to each other”. These comments caused a lot of anger among the Rossoneri fans, and rightfully so given how the journalist made it sound.

However, in my opinion, he was slightly misunderstood. If you watch the video on YouTube, it sounds like he means the persons for those three roles won’t necessarily be connected from before. Each candidate has been headhunted to assemble a dream team, even if that means putting people who haven’t worked together before in the same room. As long as they have similar ideas.

As we also highlight in the bulletin this week, Milan sort of confirmed this as there will be “a clear relationship between the ownership, the Head of Football, and the head coach”. In other words, we don’t have to worry ourselves to death about Amorim and the Head of Football, seemingly Markus Krösche, not speaking to each other. Quite the opposite.

📋 Milan Bulletin

Below, we have collected the most important Milan news from the last week, including our longer reads and newspaper reports.

📰 Latest News

As part of the Amorim announcement, Milan clarified a few things: 1) Amorim has been a target for several years, mainly thanks to his Sporting years. 2) The CEO, Head of Football, and head coach roles will be closely linked, making the chain of command shorter. 3) Three months of work were compressed into three weeks.

Ralf Rangnick was asked about his talks with Milan during a press conference last week. He confirmed that he had given the Rossoneri a deadline and that there was ‘still no clarity’ once that arrived. He also called out Italian media, especially their reports of his demands. “I smiled and chuckled,” he said.

Mattia Liberali is on the radar of several clubs after a great season with Catanzaro in Serie B, and there is a €6m release clause in his contract. Como and Sassuolo are currently frontrunners in the race, but although Milan are entitled to 50%, some fans are disappointed that they won’t get more (if they are not buying him back).

Mercato round-up: Camarda’s buy-out clause has been triggered by Lecce, but Milan are expected to buy him back; Maignan is once again being linked with an exit amid the UCL failure; Roma are exploring a deal for Pulisic, as Gasperini likes him; Amorim wants a striker similar to Gyökeres to lead the line for Milan; Rabiot might well join Allegri at Napoli.

🔍 Longer Reads

Our latest long reads include a look at Ruben Amorim and whether Milan are making an all-too-familiar mistake or not. We have also delved a little deeper into the management direction that the Rossoneri have decided to take, with the Head of Football role introduced.