14. Massimiliano Allegri – Juventus ($4.5 million annual salary)
Massimiliano Allegri played in several Italian football clubs as a midfielder. He started his senior career in 1984-1985 season. In terms of goal scoring, he had his best season with Pescara as he scored sixteen goals in 64 appearances.
He retired from professional football in 2003 and jumped into the managerial seat right away. In fact, the first team he managed was the last team he played for, Aglianese.
Allegri might have played in mediocre clubs only, but he has taken on two big Italian clubs, AC Milan and Juventus. On his first season with AC Milan, he brought the team to earn a Scudetto (winning the Italian league).
However, his last season was not so prideful as AC Milan could only finish 11th. Thus, he moved to Juventus for $4.5 million of annual salary in 2014. For all two seasons he has managed the club, Juventus has won all three Italian trophies: Serie A (Italian league), Coppa Italia, and Supercoppa Italiana.