Since Scotsman John Tait Robertson was appointed as Chelsea’s first boss way back in 1905, the Blues have had a total of 36 permanent and short-term managers. The last two decades have seen the club’s greatest period of success and a host of big name managers, including Jose Mourinho and Carlo Ancelotti have graced the dugout at Stamford Bridge during that time, but have they enjoyed a fruitful career after leaving west London?
Mourinho arrived to much fanfare in 2004 after lifting the Champions League trophy with Porto, and the “Special One” lived up to his billing with an extraordinary debut season as Chelsea won the Premier League for the first time in 50 years. The Blues retained the title a year later and completed a domestic double in 2006/07 before Mourinho made a shock exit later that year.
The Portuguese moved to Inter Milan in 2008 and led the Serie A giants to back-to-back Serie A titles, and became only the fifth coach to win the Champions League with two different clubs in 2010 when his side defeated Bayern Munich 2-0 in the final. Real Madrid came calling after his success in Italy but Mourinho’s three-year tenure at the Bernabeu is the arguably the leanest of his career in terms of trophies, with just one La Liga and a Copa del Rey.
His incredible rapport with the Chelsea fans played a major role in Mourinho making a long awaited return to the club in 2013, and another Premier League title and League Cup win followed before he was sacked in 2015. The former Barcelona translator showed his enduring qualities this year when he lifted the Europa League trophy for the second time in his career with Manchester United, but 888sport are among a growing consensus of critics that believe his reliance on defensive tactics could make long-term success at Old Trafford difficult.
Mourinho claimed he was still Chelsea’s “number one” earlier this year but several other managers have also been popular with the Blues faithful since the turn of the millennium. While Claudio Ranieri didn’t win any major honours during his time at the club between 2000 and 2004, his affable nature and hard work to transition the side following Roman Abramovich’s arrival made him a fan favourite.
The Italian enjoyed little success in his next seven managerial roles but he and Leicester City stunned the footballing world in 2015/16 when the Foxes won an improbable Premier League title. Chelsea played their part by defeating Spurs to ensure the trophy went to the King Power Stadium, and Blues fans showed their love for their former boss by giving him a standing ovation and chanting his name during the final game of the season at Stamford Bridge.
Another Italian, Carlo Ancelotti also enjoyed a short but prolific stint as Chelsea boss, with a top flight and FA Cup double during the 2009/10 season. He has since won Ligue 1 with Paris Saint Germain and made history at Real Madrid by lifting the club’s tenth Champions League trophy. The former AC Milan boss moved to Bayern Munich in 2016 and clinched the Bundesliga title in April.
A rundown on managers wouldn’t be complete without mention of Roberto Di Matteo, the only Blues boss to bring the Champions League trophy back to the Bridge in 2012. Unfortunately, Di Matteo has struggled during permanent stints at Schalke 04 and Aston Villa, and is now out of work. Meanwhile, Rafa Benitez won the Europa League with Chelsea but his previous ties with Liverpool and other factors meant he was never embraced by fans. He has since had a brief tenure at Real Madrid and is set to manage Newcastle United in the EPL next term after guiding them to the Championship title.