Fun start to the summer [Newsletter]

Jun 04, 2026

🤯 That was one way to announce it…

I can’t be the only one who feels the whole Rafael Leao announcement was a little bizarre, surely? After such a long time at the club, leading them to the Scudetto in 2021-22, it would have been appropriate with a MilanTV interview or something of that sort. Casually announcing it in a random interview with Portuguese TV, while wearing sports slippers (I presume), was no way to do it.

This isn’t me placing blame on Leao either, just to be very clear. The situation at Milan is chaotic right now and he probably felt it couldn’t get any worse, which is fair enough actually. It’s just said how things have developed over the last few years because at the end of the day, he’s our star player. We all more or less expected a departure this summer, I know, but we couldn’t even get that right.

It will be very interesting to see how much money Milan can get for their No.10, especially now that every single club knows he wants to leave. That undermining position is totally on Leao, without a shadow of a doubt, but I’m willing to give him the benefit of the doubt here. I just can’t be bothered with another infected departure involving a player who has given us so much.

💰 World Cup boost

Since Milan are still talking to several candidates for the head coach role, I’m going to focus on the World Cup instead, hopefully coming back to the manager next week. The Rossoneri will have ten players at the tournament: Maignan and Rabiot (France), De Winter and Saelemaekers (Belgium), Estupinan (Ecuador), Gimenez (Mexico), Jashari (Switzerland), Leao (Portugal), Modric (Croatia) and Pulisic (USA).

Several of these players could end up leaving this summer, so for Milan, the tournament could definitely act as a boost of sorts. Leao is a great example as a strong run with Portugal, along with his desire to leave, could result in several clubs lining up. Gimenez is another one after a very tough season, especially since some of the clubs that are already monitoring him might be doubting his qualities.

That said, it will be a little bit strange to follow these players during the tournament. Usually, you can be pretty sure that they will stay at the club (making it easier to root for them), but now we are in a weird in-between where everything can happen with a completely new management in place. Nevertheless, albeit perhaps not for the Italians, it should be a fun one in North America.

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📋 Milan Bulletin

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

📰 Latest News

Despite the fact that the results for Milan Futuro have been largely negative, the director of the project Jovan Kirovski is reportedly in line for a new contract. Speaking of which, the club did tie two young talents down to their first professional contracts: Luca Menon and Mattia Mercogliano.

Sadly, the chaos at the management level means Milan are at risk of losing one of their most promising young talents on a free transfer, as Simone Lontani seems to be Parma-bound. Not only that, but goalkeeper Alessandro Longoni appears to also be heading away on a free.

The picture is constantly changing, but at the time of writing Oliver Glasner is the frontrunner to take the head coach role with or without Ralf Rangnick’s arrival. He had a six-hour meeting with the leadership on Tuesday in Germany, which he showed up for well-prepared.

Mercato round-up: More Italian influence is expected in the squad for next season; some big names could leave amid the confusion at management level; Spurs are targeting a Milan striker; Nkunku is now expected to stay for a few reasons; a Celtic midfielder has been linked; Leeds United could come in for a midfielder after the Okafor signing.

🔍 Longer Reads

We have had quite a few long reads over the past week for you to sink your teeth into, including why it became logical for Andoni Iraola to reject Milan, the irony of the Rossoneri’s rekindled Rangnick pursuit, and a look at how the start to the summer has been one battle after another.

We also put together our awards for 2025-26 including the best, worst and everything in between, while a Liverpool insider revealed all to us about the Arne Slot links, and there was a piece on the internal divisions that have emergeddespite the power vacuum.