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#2 Carlo Ancelotti
Carlo Ancelotti is one of the most decorated managers of the current era. Having managed some of the best teams in the world and has won the Champions League on three separate occasions with two different teams.
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He is the third manager in our list to have managed Chelsea at some point of time. We'll come to that later, let's start with his initial days as manager.
He started out with Serie B team Reggiana and helped them secure promotion in his first season itself, in 1995. But he shot to fame in 1999 when he was announced as the manager for Juventus, though his spell there was not that fruitful.
He managed the AC Milan team when they were in their prime. In the eight-year spell as the manager AC Milan won the Serie A once, Champions League twice and Coppa Italia once. It was after this spell that Chelsea came calling.
He joined in the 2009-10 season and by the time he left, Chelsea had won the EPL title once, FA Cup once and the Community shield once. So, this list wouldn't have been complete without mentioning this eyebrow-raising Italian.
