Claudio Ranieri | Sep 2000 – May 2004
Affectionately known as The Tinkerman for his fondness of rotating players at a rate of knots, the Italian arrived at Stamford Bridge pre-Roman era, and did fairly well, finishing runner-up to a tremendous Arsenal side, and reaching the Champions League semifinals with a talented Chelsea squad only to mystify just about everyone with his bizarre team selection, resulting in a heavy second leg defeat which was enough to see him become the first coach sacked by Abramovich.
Was the sacking harsh? Yes, it can be argued following the success he achieved, but he wasn’t the level of coach Roman desired after purchasing the West London club, and the embarrassing defeat to Monaco coupled with the constant changing of the team was enough reason for Roman to wield the axe.
Ranieri would go onto manage a whole host of teams in Europe before returning to England and miraculously winning the Premier League with perineal underdogs Leicester City.
Why He Deserved The Sack
Could never settle on a regular team. Didn’t seem tactically good enough at the highest level. Not enough worldwide pedigree to attract the best players. Bought a lot of duds.
Jose Mourinho | Jun 2004 – Sep 2007
Fresh off winning the Champions League with the unfancied Porto, Jose Mourinho was hired by Roman to make Chelsea the Kings of Europe. Upon arriving at Stamford Bridge, The Portuguese rifled feathers by declaring himself The Special One. He would go on to prove those words, winning the club’s first English League Title in over 50 years. By the time he left, he had won back-to-back titles, two league cups and a FA Cup. By anyone’s standards, Mourinho was a success at Chelsea.
However, not everything was plain sailing with Mourinho. He was a hard manager to play under, got under people’s skin, and played a pragmatic style of football that didn’t sit well with Abramovich. The final nail in the coffin came when Jose clashed with Roman over certain signings, finally getting the bullet one month into his fourth season following a 1-1 draw with lowly Rosenberg.
Mourinho went to Italy, joined Inter Milan and won a historic treble to get his career back on track before crumbling under the pressure at Real Madrid and returning to Chelsea (more on that later), then having limited success at his supposed dream job at Manchester United, only to get sacked and agree to become Tottenham manager. How the mighty have fallen.
Why He Deserved The Sack
Constant falling out with the owner. Rifling feathers with players who dared to question his methods. A dire style of football. Always questioning referees motives. Being public enemy number one and bringing bad press to the club.
Avram Grant | Sep 2007 – May 2008
A close friend of Abramovich, Grant was parachuted in from his technical director role at the club to replace Mourinho, much to the shagrin of the Stamford Bridge faithful. Despite not being a fan favourite, and a charisma vacuum, Grant was extremely successful at Chelsea, finishing second in the league and only losing the Champions League final on penalties to Manchester United after John Terry unfortunately slipped when taking his. He also has the best win percentage of any manager under Abramovich.
He was sacked shortly after the European final defeat in Moscow after reports claimed Roman was embarrassed to lose in his home country. Players were said to be disappointed at the sacking, having a good rapport with the manager, who was the polar opposite of Jose in his man-management skills.
Following his sacking, Grant stayed in the Premier League, gaining many plaudits for his defiance with Portsmouth despite their severe point loss and subsequent relegation, they lost out on the FA Cup to Chelsea, of all teams. He also had a less than impressive stint at West Ham.
Why He Deserved The Sack
Failure is not an option at Chelsea. Avram Grant led Chelsea to three failures in one season. Losing to Spurs in the League Cup, and Manchester United in both the League and Champions League, the latter of which happening in Roman’s homeland of Russia. He was also extremely boring with the media, not well known, and most claimed he was just riding Jose’s coattails.