When you think 'da milan'..
The whole 'champion elite champagne family football' image around Milan is part of the Berlusconi era, always has been. It's an image he wanted Milan to have (for multiple reasons), the big stars with big personalities (think Gullit and MvB) needed to be at Milan and attractive football was expected. This is all fine and well when the money for it is there. Maybe the whole elite image is a bubble but nobody bats an eye when there's the money and power to back it all up.
What happens when the money and power is not there anymore to back that image up? It requires adequate foreseeing and a change of habits maybe even culture within the club. You can't buy the Gullits, van Bastens and Nesta's anymore, for whatever reason, which route do you take? In Milans case they didn't take any route. The bubble of champion elite champagne football and club is still lingering around, hence you see 'champions' like Torres arrive. Players who have that image that Milan wants it players to have but are past it, there have been many. The real champions are just too expensive to buy or keep (Silva, Ibra)
When the same thing happened with clubs like Ajax (used to be bigdog now not so much) they foresaw it and started heavily investing (already had a very solid tho) in youth system. Relative to a club like Milan they have low financial ability but over the last few years have been able to stay competitive despite (again relative to their financial position) selling their best players every single year. Their youth system is able to produce new first team worthy players every year but they don't have the financial power to keep them at their club for a longer time. Milan on the other hand has.
From players like De Sciglio, El Shaarawy, Saponara, Niang, Cristante to Pato and even slightly older talented players like Urby, Poli, Constant etc. Players who show potential at the start of their Milan career but fade away or even regress as time goes on.. For me it confirms the focus is all wrong. The champion elite champagne phase of the Berlusconi era is over, the money is not there anymore. If they want to maintain that image, they should (partially) sell. Otherwise more youth is inevitable.
Not saying Milan should be a full on youth developping team like Ajax or even Arsenal, but daring to invest an 8m sum into a talent instead of a freebie 4m net wage 'champion'. Look how Juventus 'made' players like Pogba and Vidal into champions and are able to hold onto them (for now). Also this is not a knock on the trainers at Milan who didn't give youth a chance, this all is above them and deeper into the clubculture.