The question you have to ask is, with the teams he had over that space of time, would you expect anything less than what he's achieved? For 5 of the last 9 seasons he was in control of squads that were arguably the best in the World, at Inter he took over a team that were already dominating Serie A. Now to be fair to him there's only a handful of managers that would be able to meet those expectations to the same level of success but that doesn't really change the fact that not winning most of those trophies would have made him a failure.
If he wins it all with Chelsea this season, I'll be a little more impressed.
