They say that, with Abramovich, you always have to prepare for the illogical. At the time they thought it utterly illogical to sack Jose Mourinho and replace him with Avram Grant, even if Grant then guided Chelsea to within a whisker of a European and domestic double. Grant, of the six managers Abramovich has so far employed, has gone closest to delivering the dream and satisfying that so-called obsession.
But, if Abramovich does dismiss Carlo Ancelotti, either in the next few days or at the end of what has been a hugely disappointing season, the decision would be a product of both aspects of the oligarch's character. Part anger and part of a possible plan that was hatched a couple of months ago when Chelsea were really struggling.
Marching orders? Ancelotti (centre) could face the axe from owner Abramovich
Abramovich's mind would have been clouded at Old Trafford on Tuesday by bitter disappointment - by the failure, once again, to deliver the trophy he so craves.
Defeat by Manchester United, like defeat by Inter Milan last season, would have sparked the customary autopsy but it would have also left Abramovich feeling hugely let down by a man he considered to be the answer. There will be part of him that wants the Italian to go immediately.
That forgets the domestic double Ancelotti delivered in his first season in English football and sees only the crushing elimination at the hands of Mourinho last season and the manner of this defeat, with the nightmare over the selection of Fernando Torres.
Does Abramovich tell his managers which players to pick? Sources at Stamford Bridge insist not, and Mourinho maintains to this day he was never ordered to play Andriy Shevchenko.
The incredible sulks: Torres (left) is drawing comparisons with Shevchenko, having also struggled to replicate his goalscoring exploits after his own move to Stamford Bridge
There was 'always that bad smell in the room', as one close observer put it yesterday, but the evidence of the two legs of this season's Champions League quarter-final would suggest Mourinho handled it better than the Italian. Where Mourinho often had the courage to omit Shevchenko, Ancelotti has buckled under the pressure of that ?50million price tag.
The selection of Torres in both legs - first alongside Didier Drogba, then in his place - was nothing short of a disaster; a major factor in why Sir Alex Ferguson is relishing the prospect of a fourth Champions League semi-final in five years and why Ancelotti fears for his job. Abramovich is sure to interpret it as weakness, perhaps concluding, however unfairly, that Ancelotti does not have the strength to cope with the pressure of working for him.
Is is significant that Ancelotti went to Chelsea as 'first-team coach'? He leaves transfer business to others - as he did at Milan - preferring to focus on matters on the training pitch.
Mourinho is certainly different, and so, for that matter, is Guus Hiddink. They are managers with the ego and the personality to deal with an owner like Abramovich, even if the clashes with Mourinho did result in his dismissal.
The Special One: Mourinho (centre) was a victim of Abramovich's wrath despite winning back-to-back league titles
Ancelotti could respond to that by pointing to his record at AC Milan - two European Cups and one Serie A title among the eight trophies he won in eight years in charge - under Silvio Berlusconi.
Against him, though, is his muted reaction to the dismissal of Ray Wilkins, his failure to revive a team who threw away a commanding lead in the Barclays Premier League this season and the indecision that seemed to affect his judgment when it came to picking his team at Old Trafford this week.
His allies, and Ancelotti has many who recognise his qualities not just as a fine coach but as a thoroughly decent man, say there is a flip side to that particular argument.
They say Ancelotti is a proud man who was deeply wounded by the way his employer undermined him over Wilkins; who expects to be shown a bit more respect.
He is still at Chelsea, they insist, because he believes in his players and it would not be his style to walk out suddenly. But he is unlikely to put up much of a fight should Abramovich decide to bid him farewell, especially when there seems to be a job waiting for him at Roma.
Even before his side lost to United, Ancelotti had to deal with Ron Gourlay, the club's chief executive, publicly declaring his position would be reviewed at the end of the season, which again was not exactly helpful.
Winner: Hiddink led Chelsea to FA Cup glory during his brief tenure in 2009
Hiddink might be the answer but, when the pain of disappointment subsides, Abramovich does need to go through a period of introspection and examine his own role in this sorry mess.
It is not Ancelotti's fault that, despite spending more than ?70m in January to take his overall investment at Stamford Bridge to the best part of a billion, an ageing team are in serious need of an overhaul.
Nor can he be blamed for failure in the five Champions League campaigns prior to his arrival. It has more to do with a lack of continuity and in the fact that Abramovich clashed with Mourinho and made a mistake when it came to Luiz Felipe Scolari.
The precise reason why Wilkins went still baffles many Chelsea insiders but sacking him destabilised the dressing room, upset the coach and damaged his position in the eyes of the players. When he sang on that open-top bus there seemed a genuine affection for him. Now insiders say that warmth is mixed with disappointment. Wilkins was a popular figure.
Happy days: Ancelotti was believed to be against the dismissal of assistant Ray Wilkins (right)
But is the answer to dispense with Ancelotti as well? Abramovich hired him in the first place because of his record in Europe and the success he enjoyed last season demonstrated an ability to galvanise a new team and deliver success.
What the Russian should do is authorise further investment in players and provide Ancelotti with the support he has said he always received from Berlusconi when times were tough.
That way, he might just win the Champions League. Sacking the manager and starting afresh certainly has not paid off so far.
Get Guus back! Abramovich has his heart set on Hiddink return to Stamford BridgeKeep Carlo! Cech insists Ancelotti is best man, despite European setbackAll the latest Chelsea news, features and opinion
Explore more:People: Alex Ferguson, Didier Drogba, Roman Abramovich, Fernando Torres, Luiz Felipe Scolari, Jose Mourinho, Carlo Ancelotti Places: Milan, Europe