5) Giovanni Trapattoni
Il Trap is arguably one of the most respected personalities in Italian football for his services rendered as both player and coach. He spent the majority of his playing career at AC Milan but managed a host of top clubs and international teams including Milan, Juventus, Inter, Bayern Munich and Italy.
Player: In a 13-year career, Trapattoni spent 12 seasons at AC Milan. He could play both as a centre-back or a defensive midfielder. With Milan, he won the Serie A title twice. But his biggest achievement with the club was winning the European Cup twice – in 1963 and 1969.
The 1963 final was special as he was tasked with keeping Benfica legend Eusebio on a leash. Although the Portuguese striker did score early on in the game, Trapattoni managed to mark him out of the game as Milan came back to win 2-1.
Manager: As a manager, Trapattoni won plenty of league titles, even winning them in four different countries. But he won the European Cup just once – during his stint with Juventus. The Old Lady reached the final in 1985 where they beat Liverpool 1-0 thanks to a Michel Platini penalty.