I think Milan’s issues come down to two categories:
- Strategic limitations tied to financial directives
- Execution of the sporting plan.
Starting with execution, since this is the more obvious one: signings like Musah and Chukwueze came at the expense of more urgent profile needs. That shows a bit of naivety from our group, the belief that stashing undervalued talent would naturally lead to upside, instead of focusing on coherence and balance. I expect this to improve under a competent SD.
Then come the structural limitations. You see it in decisions like holding on to Theo and Leao despite clear stagnation, or sticking with Bennacer rather than pivoting to someone like Kephren Thuram. These aren’t just tactical choices, they’re attempts to extract value from past decisions rather than move forward with clarity.
Now look at Juventus. They’ve not only spent heavily, they’ve also shown a willingness to cut losses quickly. If a signing doesn’t fit, they move on, even if it means selling for less. They understand that sunk cost plus opportunity cost matters more than trying to salvage bad investments. Is Milan ready to take that approach? That kind of decisiveness requires consistent financial backing, not just one-off transfer splurges. And the problem is,
when Milan fails and loses money, the reaction is usually to become more risk-averse, which only makes it harder to correct course. Instead of cutting losses quickly, we double down, hesitate, or try to “make it work” and that hesitation becomes its own cost. Before anyone tries to say I’m hyping Juventus, I’m not. I’m simply pointing out the difference in investment strategy and decisiveness between them and us.
This is also why the idea of “we’ll go all out when the right one comes” feels like wishful thinking to me. A good sporting director improves your odds, helps avoid obvious missteps, and may spot undervalued opportunities. But even the best can’t guarantee that every transfer will work out, even super competent Berta thought it was a good idea to go all out on Joao Felix.
For me, the bigger question is about ownership’s stance. Are we going to keep posturing with “Berlusconi 2.0” slogans to rile up fans, or will we finally accept that our best shot is to function more like Dortmund, Porto, or Benfica—clubs with clear models, alignment between sporting and financial goals, and realistic expectations? That kind of clarity is far more important than any individual appointment.