2. Carlo Ancelotti
There are few players who can claim to have won the European Cup twice, in successive seasons as a player. There are even fewer players who have won the European Cup twice as a manager. But, there is nobody apart from Carlo Ancelotti, who can claim to won the European Cup twice as both a player and a manager, with the same club (AC Milan).
As a player, Ancelotti won the Serie A thrice, twice with AC Milan and once with AS Roma. He also won the UEFA Super Cup and the Intercontinental Cup twice in successive seasons with AC Milan. As a manager, he has won everywhere he has been. He is one of a select few managers to have won the League in England, Italy and France. He has also been awarded the Serie A, Ligue 1 and UEFA Manager of the year. He is currently at Madrid, trying to pick up the League title there as well, so he can rightfully claim to have won the league in four different countries, something not many can lay claim to.
With such a stellar CV, you might be tempted to think that there can’t be anyone better than this, but you are in for a surprise when you find out who is number one on the list.