#1: Giovanni Trapattoni

Back in his playing days, Giovanni Trapattoni was an absolutely revered figure at AC Milan. Trap spent his entire career with the Rossoneri and could have been a one-club legend if it hadn't been for his one-year spell with Varese in 1971.
Although he spent 12 years at the club, Trapattoni returned to manage AC Milan three years after his retirement in 1972. The Rossoneri were delighted to welcome their legend, but the excitement was short-lived.
After just one season, Trapattoni stabbed a dagger into the hearts of AC Milan fans by agreeing to coach rivals Juventus. Trapattoni was a huge hit with the Bianconeri who won loads of titles during his tenure of a decade from 1976. It was here that he earned his recognition as one of the best managers in the history of the game.
But, Trapattoni committed treason again by joining rivals Inter Milan for a stint of five years. The Bianconeri fans suffered the same fate as AC Milan supporters. Yet, Juventus welcomed him with open arms back for a second spell in 1991. Quite a brave man!