Maybe to Model some jeans. I don’t think he would go there to coach. The Italian clubs don’t have the same level of funds.
For the historic side maybe but the league wouldn’t challenge him mate
He loves Italy, he's said he'd like to manage there in the future and it's the only serious league he hasn't won yet. It's his obvious destination after leaving City, the only question is when and whether the league is interesting enough. He almost went to Milan instead of Bayern in 2013.
For the past 10 years it's just been Juventus hegemony, now Napoli, Milan, Inter, Roma and Lazio are all genuinely competing for the title.
RedBird Capital have the money to make Milan go deep in the Champions League as well.