Milan head into next week without a head coach, a sporting director, a technical director, or a CEO. That's the full senior structure gone in one swoop — and the clock is ticking.
Two meetings will go a long way to defining what the club looks like next season. Ralf Rangnick sits down with the Austrian FA on Monday to discuss his future. Oliver Glasner meets with Milan's remaining representatives on Tuesday. Both conversations will carry real weight.
Rangnick: the architect Milan want to build around
RedBird's preference appears to be Rangnick in the sporting director role rather than on the touchline. That's a significant distinction. The German built his reputation at TSG Hoffenheim, guided consecutive promotions, and then shaped the Red Bull football network from above — influencing the careers of Jurgen Klopp, Thomas Tuchel, Julian Nagelsmann, and Glasner himself in the process. He understands how to construct a club, not just manage a squad.
The Austrian FA want to keep him. That's understandable — he's their best option and they know it. But Rangnick knows what's being offered from Milan's end, and a project to reshape one of European football's most storied clubs is a different kind of challenge entirely.
Glasner arrives fresh off a trophy
If Rangnick ends up overseeing Milan's football operation, Glasner as head coach makes immediate sense — they know each other's methods, and trust matters when you're rebuilding from scratch. Glasner just won the 2025-26 Conference League with Crystal Palace, beating Rayo Vallecano in Leipzig. Three trophies with Palace. His stock has never been higher.
That makes Tuesday's meeting genuinely competitive. Milan aren't the only club aware of what Glasner has done at Selhurst Park, and anyone pricing up Serie A winner markets next season will want to know who ends up in that dugout before committing.
By Tuesday evening, Milan's picture should be significantly clearer. Whether it's clear in the right way is another question entirely.
