One of the problems of the modern game, to me, is the empowering of Director's of Football who reserve to themselves the decisions on signings.
The managers are less of a manager and are becoming solely coaches.
Ancelotti is high profile manager, if you consider his record, and should have a say on the squad shape. We may argue if Silva was a modest manager but Ancelotti is one of the top managers of the decade.
He is far from being outdated, in my opinion. He's hugely experienced as a manager and as a former top class football player.
So signing Ancelotti is, to my eyes, a top, top decision. It's like opening a restaurant and having a top chef.
Now, provide him the resources (which are not necessarly financial) and let the man work. We are in January so I think we should be able to offload some rotten tomatoes.