Recreating an all-time Milan XI is always incredibly challenging because you inevitably have to leave out some monumental names. Clearly, this is just a fun exercise, and the lineup I’ve proposed is far from perfect—there could easily be ten other equally (if not more) valid versions. That said, I’ve opted for a modern 4-3-3 formation because it felt sacrilegious to leave out one of the three legendary strikers who shaped Milan’s history. The good news is that all three forwards have vastly different skill sets, so, in theory, it’s possible to fit them into an all-time lineup.

Goalkeepers
From a pure talent perspective, Albertosi deserves a place here, but I simply don’t associate him with the Rossoneri shirt—he’ll always be a Cagliari legend to me. Dida, on the other hand, might not have been as otherworldly as some others, but he reached incredible heights and, at his peak, was undeniably world-class. I’m giving him the nod here, though it’s just as valid to choose Sebastiano Rossi, who demonstrated remarkable consistency over the years.

Defense
What a defense, folks! Honestly, it might be the best in football history. All Italian, three of them played together and knew each other’s movements by heart. I could’ve shifted Maldini to the center and put Schnellinger at left-back, but I loved Maldini as a full-back. He was a freak of nature: powerful, fast, technically gifted—just unstoppable. He’s staying as my left-back. Tassotti might not have been a world-beating full-back, but his impact in a Milan shirt was enormous, and he deserves a spot. Nesta? One of the greatest center-backs of all time and the perfect partner for Baresi.

Midfield
Okay, okay, I could’ve included players like Pirlo or Liedholm, and they wouldn’t have looked out of place—I get it. But Rijkaard is non-negotiable for me. He offers balance in both phases of play, physicality, excellent technique, aerial threat, and midfield dominance. Rivera is also a must-have. The “Golden Boy” made Milan history and was one of the club’s earliest legends—he simply has to be here. Next to him, Pirlo could’ve fit, but in my opinion, he needs a different context to truly shine. That’s why I chose Schiaffino. He was a phenomenal midfielder who doesn’t get enough credit: a playmaker, attacking midfielder, or even a libero later in his career. He had outstanding tactical intelligence, sublime technique, dynamism, vision, and a sharp footballing mind.

Attack
As mentioned earlier, Milan’s attacking options are just devastating. It pains me to leave out Gullit, but I can’t justify removing any of the three strikers I’ve selected (or one of the midfielders). Van Basten is the prototype of the perfect number 9: physically strong, intelligent, supremely skilled, elegant, and excellent at linking up with teammates. Nordahl was an unstoppable force of nature—a cyclone of raw power and incredible goal-scoring instincts. Sheva, for me, is somewhere between Van Basten and Nordahl: he moved intelligently between the lines, linked up well with teammates, and was a complete, brilliant forward.