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I agree, many people are looking at this like it's a big deal, like because his last time wasn't great, but the reality is, just because his last term was bad, doesn't mean this has to be bad too. We should be looking into this as a good thing for Milan.
We will definitely see them improve and shouldn't really consider this as bad, we should see this as a good thing. We are improving a lot and for that reason we are going to see Milan probably make a ton of money, not going to be that bad at all. If we could see them be in the top four during the first season, then they can fight for the top pace a year later. So give Allegri 2 years, and I think there is a possibility of a title, unless some other team does incredibly well.
It is 11 years ago that Allegri was the AC Milan coach for the last time. Within 11 years everything changes. I don't know i. there is a single player still playing from back then, but I doubt it. In the meantime he collected 12 national titles in Italy, I think that is proof enough to say that not too much can go wrong here. You never know in advance, but the probability that this goes utterly wrong is rather low as he is a proven expert as the titles substantiate.
Changes for the players could be inbound too. He knows what he wants and I think they will a few transfers. Whether he is a fan of players like Pulisic or not, it remains to be seen but he likes consistency and Pulisic is someone who can't bring it every weekend.