In June 2003, Roman Abramovich bought Chelsea from Ken Bates, in a deal worth £140m. Since then the Russian has hired multiple managers over the course of his 16 years of his leadership. Many have been successful, winning multiple trophies; 5 Premier Leagues, 5 FA Cups, 3 League Cups, 2 Community Shields, 2 Europa league titles and the coveted Champions League trophy. Of course not all his appointments have been successful, but in this article, I’m going to go through my top 3.
It is to nobody’s surprise, Chelsea’s most successful manager is in the number 1 spot. Abramovich’s first appointment as Chelsea’s owner. Jose Mourinho replaced Claudio Ranieri, a fan favourite at the time which meant Mourinho had a tough job in pleasing Stamford Bridge and boy did he succeed. Everyone knows about his infamous first press conference, where he announced himself as the ‘special one’ to the world. He wasn’t wrong as he went on to become every Chelsea fan’s special one.
Under his guidance Chelsea won back to back Premier League titles, breaking the record for the least goals conceded and most points in a single season. He also won the FA Cup, 2 League Cups and the Community Shield. He held the record of most competitive home games unbeaten which at the time was 64. Jose had completely transformed Chelsea, from a good side to one of the best and most feared in all of Europe. He became Chelsea’s most successful manager ever, winning 6 trophies in 3 years.
Mourinho unexpectedly left Chelsea in September 2007, during the beginning of the 2007/2008 season ‘by mutual consent,’ breaking every Chelsea fan’s hearts. Rumours speculated this was due to disagreements between Jose and Roman, involving the hiring of Avram Grant.
However, this was not the last Chelsea fans would see of Mourinho. On June 2013, Abramovich re-appointed Mourinho as manager, much to the joy of the fans, who had yearned for his return for years. During his second tenure Mourinho won the Premier League and League Cup further adding to his haul. Sadly, not all love stories have a happy ending and in his third season, Chelsea never kicked off, having their worst ever start to a Premier League season. This resulted in Mourinho leaving Chelsea for a second time. Mourinho will forever be remembered for his charm, humour, his relationship with the fans and of course his trophy cabinet speaks for itself. Not only the best manager Chelsea have had during the Roman Abramovich era but the best Chelsea manager of all time. Who knows, maybe the future could have a third spell for Mourinho at Chelsea.
In June 2009, Roman hired Ancelotti to succeed the then interim manager Guus Hiddink. In the August, Ancelotti won his first trophy as Chelsea manager, winning the Community Shield against Manchester United. He led Chelsea to their first Premier League title since Mourinho left, and that too with style. His teams were great fun to watch, scoring a lot of goals on the way, securing the title with an 8-0 victory over Wigan at Stamford Bridge. He set the record for most goals in a single season which was 103. He later went on to win the FA Cup as well beating Portsmouth in the final, securing 3 trophies in his first season. After the numerous Chelsea managers that were hired and sacked after Mourinho, Ancelotti became the first to have success and a bond with the fans. This wasn’t to last as he was sacked the following season, despite finishing second in the Premier League. A move which still baffles most fans to this day.
Abramovich hired Conte on the 4th of April 2016. He would start after he finished his job as Italy manager while they competed in the Euros. During the competition, he showcased his ability as a manger, leading Italy to the quarter finals, with what was described as, ‘the least talented Italy squad ever,’ and his passion. His start to the season was a little rocky, but after a 3-0 humbling defeat to Arsenal, Conte changed the formation to a 3-4-3 which proved to be a tactical masterstroke. Chelsea went on to set multiple records, 13 wins in a row, a record 30 wins in the Premier League, and of course the Premier League title. Sadly, Conte couldn’t achieve the double, losing to Arsenal in the FA Cup final, but he made up for it a year later defeating Man UTD to win his first domestic cup in England. Things didn’t end well off the pitch with Conte and Chelsea, but for just his achievements at the club, he makes the top 3.
Honourable mentions go to Maurizio Sarri, for his one season in which he won the Europa League, narrowly lost the League Cup final on penalties to Manchester City and finished third in the league. All while being up against a lot of the fans, media, pundits and having the tough task of changing Chelsea’s philosophy from a defensive, counter attacking team into an attacking possession-based team. Another honourable mention is for Roberto Di Matteo, while he was sacked within 8 months, his triumph in the coveted Champions League, against all odds, giving Roman Abramovich and the fans something they have desired since the Abramovich era began.