5. Letting Michael Ballack leave.
At the end of Ancelotti's double winning first season in charge, Chelsea made the decision to let Michael Ballack leave on a free. Ballack's contract was up, he was 33 and he was one of Chelsea's highest earners - sounds like the ideal time to let him go. Chelsea then signed a young Brazilian midfielder to replace Ballack, and all seemed rosy. However, Ramires struggled to settle down and his performances were nowhere near as good as what we had seen from Ballack the previous season.
Paul Merson famously said that Ramires wasn't "fit to lace Ballack's boots" after one of his poorer performances. I interviewed Martin Lipton from the Daily Mirror last year and he said that if Ballack had stayed then Chelsea would have won the a second Premier League title in a row. Lipton told me how Ballack was Terry's equivalent; they didn't always get on but when Terry was down, it was Ballack who got the players going. So not only was he still an excellent midfielder, he was also vital to the dressing room. Ballack had expressed his desire to stay multiple times and I still don't understand why the board let him go.
4. Sacking Carlo Ancelotti.
Without a doubt, Ancelotti was one of the best managers in the world and still is. He won the Premier League title and the FA Cup in his first season in charge; if there was ever any doubt that he was a world class manager, he proved it that season. He finished his second season in charge trophy-less, due to no fault of his own in my opinion. Drogba caught malaria at the start of the season. Essien, Malouda and Lampard, meanwhile, who were all key figures in Ancelotti's first double winning season in charge, all missed large portions of the season through injury.
Abramovich then went out and bought a new toy, also know as Fernando Torres and Ancelotti then had to try and accommodate Torres, Drogba and Anelka. Ancelotti was sacked moments after the final game of the season away at Everton, a disgraceful way to treat a manager only 12 months after he had won the double.
3. Sacking Roberto Di Matteo.
I admit that I wasn't pleased at all when Di Matteo replaced AVB midway through last season. AVB's management wasn't working so why replace him with a member of his own staff? I'm glad they did though. RDM installed confidence in a team that was at rock bottom, it would have been hard to do worse than AVB but the way Di Matteo turned the team around was something special. As you all know, he was the first ever Chelsea manager to win the Champions League, he also won the FA Cup without being able to field his strongest XI in either final.
He got the three amigos playing fantastic football earlier this season and he also got Torres scoring again, well nearly. Chelsea were only four points behind Manchester United in the league when Di Matteo was sacked, there was still a chance that the team could progress through a very hard Champions League group and Chelsea were still in the league cup. Every manager has bad results but sacking Di Matteo was a pathetic and embarrassing move by the Chelsea board and replacing him with Benitez made it even worse.
2. Signing Fernando Torres.
Of course there is still time for Torres to shake off his tag of being the biggest flop in the history of football but we all know that isn't going to happen. Torres was a panic buy, he was supposed to be an instant solution to Chelsea's woes and at £50M, I had hoped so too. Step forward Shevchenko mark II. Torres has hindered the plans of every Chelsea manager he has played under, I will be very surprised if he isn't shown the door in the summer.
I don't think anyone will ever be able to give a definitive answer as to why it hasn't worked out for Torres at Chelsea but he should never have been signed. He was injury prone and had been struggling to recapture his form at Liverpool after a disastrous World Cup. At the time I thought it was the best thing ever, in hindsight it was an absolutely tragic move by the board.
1. Sacking José Mourinho.
The Special One, the best manager in the world and the winner of Chelsea's first league title in fifty years. You either loved him or hated him and I loved him. Whilst I doubt that he had intentions to stay at Chelsea forever, he should never have been sacked when he was. In three seasons he had won back to back Premier League titles and then won the cup double in the third, how on earth could the board have thought that they needed a change? I can only think that he clashed with Abramovich on a personal level, with an ego like his that can't have been hard.
He was adored by the fans and players alike. Players like Lampard, Drogba and Terry made it no secret that they would love to see José return to Chelsea. Many still hope that he will be returning at the end of the season but will his relationship with Abramovich mean that the Special One won't be returning to the Bridge?
The signings of Shevchenko and Juan Sebastian Veron were unlucky to miss out. So was the sacking of Ray Wilkins and the manner in which he was sacked. Please let me know your top five in the comments section below.