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#3 Antonio Conte
Chelsea signed Antonio Conte as their new manager for the 2016-17 season following the departure of Guus Hiddink. The Italian had good credibility in his managerial career having won Serie A thrice with Juventus.
Conte was one of the preachers of the three-man defense but at Chelsea he initially started with a back-four. It was after going 3-0 down at Arsenal that Conte famously tweaked the system to his infamous 3-4-3 and the rest is history.
The Blues endured a remarkable run of form on the pitch and, as a result, won the Premier League in Conte's first ever season in England. The following season, the Italian manager helped the London club win the FA Cup.
Unfortunately, Chelsea finished fifth at the end of the 2017-18 season which led to the sacking of Conte as the Blues missed out on a place in the Champions League. He was replaced by his fellow countryman Maurizio Sarri, who did not enjoy the best of spells at Stamford Bridge.
#2 Carlo Ancelotti
Chelsea have seen a good number of Italian managers at their helm and Carlo Ancelotti is arguably the finest of the lot. The former AC Milan manager has an immense amount of experience and is currently managing Real Madrid for the second time in his career.
Ancelotti signed for Chelsea in the summer of 2009. The following season, he led the team to the Premier League title with a margin of one point. That season was a memorable one for the Blues as they scored 103 goals in the league, the first team to achieve the feat in England's top-tier league. Chelsea also went on to win the FA Cup that season, completing the domestic double.
In the 2010-11 season, Chelsea finished second behind Manchester United in the Premier League. Despite that, Ancelotti was sacked by Roman Abramovich after which the Italian signed for Paris Saint-Germain. The Italian has now returned to former club Real Madrid for his second stint as manager.
#1 Jose Mourinho
Jose Mourinho kickstarted the revolution brought on at Chelsea under Roman Abramovich. He's easily the best manager in the club's history.
Following his heroics with Porto, the Portuguese manager joined Chelsea in 2004. His detailed understanding and analysis of the opponents made Jose Mourinho a very tactically sound manager. He was brought in by Roman to have an immediate impact and he did not disappoint. He won two Premier League titles, the FA Cup and two League Cups during his three seasons with the Blues.
Amidst rumors that Mourinho and Roman had a disagreement in 2007, the former left Chelsea to sign for Inter Milan, where he won a historic treble. After leaving his next job at Real Madrid, Mourinho eventually returned to Chelsea for a second spell in 2013.
Jose managed to win the Premier League once again with Chelsea in the 2014-15 season along with the League Cup. Much of what Chelsea are today has to do with how the Portuguese set the tone in the early days of Roman Abramovich's era.
