#4 Massimo Carrera
One of the rising stars of the famed Italian coaching system and like most of the good Italian coaches, he was a former defender who played the game at the highest level.
In terms of actual coaching experience, he is the youngest of the candidates but what he lacks in experience, he more than makes for in what he offers.
Carrera is close friend and associate of Chelsea coach Antonio Conte. It was Conte who gave Carrera his first gig in football after his retirement following a long and eventful playing career.
In his first full job as a coach, Carrerra displayed all the skills he had learned working with Conte at Juventus (as sporting director and acting coach when Conte was suspended for match-fixing) and at the Italian national team to push Russian club Spartak Moscow to their first league title in 11 years.
Carrera has changed the culture of a club renowned in Russia for being flaky and made them stronger, more tactically aware and fitter than ever.
Despite his long association with rival club Juventus as player and coach, Carrera can do a great job for AC Milan if given the chance and will bring organization, defensive discipline and a strong focus on the collective to a Milan side currently struggling for a coherent identity.