The thing is he just keeps stripping the squad, at every level, and that's why you have to question him.
It's one thing if he's letting quality players like Nasri and Fabregas go, to an extent if they want to leave he might not have a say in that.
But if you look at some of the other players he's let go, Eboué, Senderos, Eduardo, Clichy, even going back to Gilberto Silva, none of these players wanted to go. Those players had a degree of versitility if Eboué was still there they wouldnt have had to play a 12 year old non-leaguer at full back. In fact selling Eboué sums up his crazy sqaud stripping mentality, and that's why I think it's time for him to go.
He has far too much faith in his youth team, it's cost you finishing top of the CL groups in the last few seasons (which meant you faced Barca instead of say Roma last year), and it's costing you in terms of him not signing decent back up players.