Ranking every Chelsea manager of the Roman Abramovich era from worst to best 

#1 Jose Mourinho (2004-07, 2013-15)

Chelsea FC v Manchester United - Premier League

Even though both of his reigns as Chelsea boss ended in fallouts, Jose Mourinho remains not just the greatest manager of Roman Abramovich’s era, but in the club’s history altogether.

The Special One is still beloved by most fans at Stamford Bridge and with a brilliant 63.6% win percentage over two spells that saw him win three Premier League’s, three League Cups and an FA Cup it is hard to argue against it.

Mourinho is the manager who helped put Chelsea on the map, taking the club to new heights as the Blues dominated English football and quickly became a force to be reckoned with across Europe as well.

Mourinho had bags of charisma and created some iconic moments from shushing the Liverpool fans to his witty one-liners to the press. All of this helped him win over the fans.

Of course, there were plenty of dark times during his tenure as well, with both of his runs ending in major fallouts and poor runs of form, but overall his time in charge was a big success.

Whether he was the Special One or the Happy One, ultimately, he was the successful one and in this game, you are judged on exactly that.