#4 Ruud Gullit – Chelsea
The 1987 Balon d’Or winner succeeded Glenn Hoddle as Chelsea manager in 1996, while he was still a player at the club.
A superstar in his own right at the time, Ruud Gullit had joined the Blues a year prior, on a free transfer, under Hoddle. Despite the initial difficulties faced in adapting to the system, the Dutch maestro made swift adjustments to finish runner-up to Eric Cantona for the Player of the Year Award, and was named Chelsea’s Player of the Year.
When Hoddle left to take up the England job, Gullit was the natural fit for the managerial role. He had great influence in the team and commanded respect. His first season as player-manager would see the Blues lift the FA Cup, their first major trophy in 26 years, as well as a sixth-place finish in the Premier League.
He left a year later, however, because of a dispute with the club.