Last season they had the best squad in the league and he finished second, giving up the Scudetto fight few rounds before the seasons end. He's also the one most responsible for Pirlo playing in Juventus colours. This season they have worse squad than last season, but still easily better than Fiorentina's, if Fiorentina hadn't choked against Roma Milan would probably play in EL, heck, I'm far from sure they will win in Siena and maintain that third spot.
It's not hard to hire worse coach than Alllegri, but I disagree that he has Milan jumping above their arse.