#1 Vicente Del Bosque
There is no question that Del Bosque's departure was one of the weirdest and most controversial decisions in the managerial history of Real Madrid. It was ridiculously unfair, even by their own standards.
Del Bosque had delivered its ninth Champions League win to the club while managing to reach the last four of the Champions League in each of his four seasons. He managed two league titles in three years and along with that, won a Spanish Super Cup as well. All this while, players with a big reputation or "Galacticos" were brought in to the club. Allegedly, most of them were brought without Del Bosque's consent.
In 2003, after Real won the title for the second time under him, the board decided to let his contract expire. This happened week after Madrid had signed David Beckham. The board tried to minimize the damage by offering him a promotion of sorts to Technical Director. However, the Spaniard refused.
He later went on to manage Besiktas and was linked to a return to Madrid after 2007. However, he was roped into the Spanish National Team in 2008. After his removal, Real went into a spiral that saw them fail to win any trophy for the next four seasons, which was the longest drought in the club's history.