I have the feeling that Maldini is trying to build a dynasty slowly building the team and not selling key pieces even if they are 'easy' to replace. Example - Tomori sold for 50 m, new Thiaw bought for 10 m. 20 m pure profit, like 40 m capital gain and a good sub. On paper this is an amazing deal. And we had many of these offers for Theo, Bennacer, Leao, etc. And none of these players was sold. I don't think we even considered them.
Selling (as much as it is nice to grab some big bucks) is sending bad message to the players (both playing for Milan and all the rest). It means that you can have your ass shipped anytime which is not really something good for player development. And it means that we are not special in any way. Just another club that doesn't value the players as people, but only as assets. And Maldini is not that type of guy. Not that I know him personally, but I've been following this team for over 20 years and I have a pretty good idea about how it's run. And many of the former players said that Milan wasn't just their employer, but their family. Having said that I am 99% certain CDK will remain at least for another season because Maldini spent too much time negotiating for him just to throw him away after 10 months. So, unless some really good offers arrive (30+ m) and CDK himself requests a transfer, he will probably stay.
Maldini is adding important pieces to the puzzle every summer.
2019 - Theo, Bennacer, Leao
2020 - Tonali, Kalulu
2021 - Tomori, Maignan, Adli (I have no doubt he will become a good player once the bald fuck gives him a proper chance)
2022 - CDK (same as Adli), Thiaw
There are 2 problems:
1. He inherited an absolutely ass team. He is not upgrading the team he inherited, he is literally building a new team. From our 2020 team it's only Calabria left.
2. He doesn't have the money to proceed quickly and is forced to often take gambles with players like Origi, Florenzi, Dest, etc. because he can't afford the players he initially wanted. Yeah, he has some major fuck ups, but it's normal.
If Pioli quits alcohol and remembers how to play football, this is a backbone of a team for at least the next 6-7 years. And this is some serious level of talent. Yes, some players will go, but the backbone would still be there. And once this backbone gels (Pioli, I am looking at you) and Maldini adds another 2-3 important pieces (CF, RW, CM), we can start kicking some serious ass.
Point is, even if you sell players for profit or just have a shit ton of money because of the owners and you bring shinny new toys all the time, it does not necessarily mean that you are upgrading the team. Examples - Chelsea in 2022/2023, Real's Galacticos, PSG, etc.
Even the richest teams took years to be build and in our case it will probably take 2 more years before we can call Milan a CL contender again, but we are definitely on the right track (although I have major doubts about Pioli's capabilities) and selling some key players (even if it's for profit) is probably against Maldini's plan.