The Russian owner has not taken kindly to zero return on his investment.
Claudio Ranieri was the first to pay the price for the absence of any silverware, the Italian axed after less than a year of Abramovich's tenure in 2004. The Blues had finished second in the table.
Four years later it was Avram Grant informed that his services were no longer required. The Israeli had come within one kick of winning the Champions League only for John Terry to slip up - literally as well as metaphorically - during the penalty-shootout defeat by Manchester United in Moscow. Again, a second-placed finish was deemed unsatisfactory and Grant was dismissed.
Then, in 2011, Carlo Ancelotti -despite delivering a domestic double 12 months earlier - was served with his P45. And, for the third time under Abramovich, a Chelsea boss learned that second was nowhere.
Even Rafa Benitez, who guided Chelsea to a Europa League triumph, saw his interim tenure expire at the end of last season.
And so to Mourinho who, until last week, was still in the hunt for the Champions League and Premier League crowns.
A semi-final defeat by Atletico Madrid terminated their stay in Europe's showcase competition, while Sunday's stalemate at home to Norwich put paid to league hopes. Victory over the Canaries would have shot them to the summit heading into the final seven days of the campaign; third is where they will now remain.
Mourinho, of course, has long since played the 'transition' card, labelling his side everything from the 'little horse' to the 'learner driver' in the race for the title.
Learner drivers, however, very rarely tear around in a vehicle worth £250million. And, to that end, the sight of Mourinho's men running out of gas before the finish line will no doubt be of concern to the billionaire boss who has spent millions souping up his ride.
There is no escaping the fact that had Chelsea taken just five extra points from the recent defeats against Aston Villa and Sunderland and the draw with Norwich, then the title would be all but theirs – even small horses should be able to hurdle such relatively routine obstacles.
The Champions League loss came against a side assembled for £30m – that is £20m less than the cost of Fernando Torres. For no matter the merits of Atletico – and they are deserving of praise – Chelsea should have progressed, especially when leading 1-0 with only 50 minutes of the tie remaining.
At least they made it to the last four of the competition. The same cannot be said of their efforts on the domestic front. Sunderland were their conquerors at the quarter-final stage of the Capital One Cup, while the fifth-round surrender at Manchester City in the FA Cup was among their sorriest showings of the season.
Mourinho, though, has managed to offset every disappointment with the promise of a better day.
He has succeeded in trivialising his shortcomings. Individuals – namely his strikers – have been criticised, their profligacy invariably offered as justification for his side's failure.
The Portuguese will, of course, survive any post-season inquest and return next season with a squad boasting even more riches than it does already. Given the trophyless conclusion to this campaign, Mourinho's stay will be unprecedented.
Were Chelsea to sign off from successive seasons minus any silverware then that, too, would be a first. It would almost certainly mean the last of Mourinho.
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