4. Ruud Gullit
One of the most colourful personalities to have ever graced a football pitch, the enigmatic Dutch man Rudd Gullit occupies the 4th position in this list.
The proponent of ‘sexy football’, Gullit was appointed as player-coach at Chelsea in 1996 following the departure of Glenn Hoddle. His arrival ushered in a new era for Chelsea as in his first season in charge of this dual role, he led the club to an FA Cup triumph and with that, helped break a 26-year-old trophy drought for the West London club.
In doing so, he became the first non-British manager to win a major trophy in England. His arrogance though was said to be his downfall as he was sacked in just his second season in charge when Chelsea were second in the Premiership and progressing well in the cup competitions.
His last appearance as a Chelsea player was against Arsenal in the League cup semifinal. His time at Chelsea can be called a success even with his premature sacking.
Apart from breaking the trophy duck, he also brought in players of the quality of Gianfranco Zola and Gianluca Vialli into the club. The latter would be chosen as his successor as player-coach and would also enjoy a fruitful spell in charge.