With Pep Guardiola opting for Bayern Munich and little discernible sign of anybody, including Rafael Benitez himself, expecting the current managerial arrangement to last beyond the end of the season, Roman Abramovich finds himself back at a familiar drawing board.
Money can buy you most things in football but not, it would seem, the manager of your choice. There has actually been a long-standing myth that Abramovich's pounds 1?billion Chelsea investment has ensured that he always gets what he wants, but the list of those who have said 'no' is longer than commonly imagined. From a failed personal visit to Highbury to offer pounds 50?million for Thierry Henry in 2003 to this week's Guardiola snub, Abramovich has suffered his share of knock-backs.
The question, though, as he approaches his 10th anniversary at Chelsea, is whether his ownership method, notably the ruthless treatment of managers, has now become the biggest obstacle to the club's progress.
It was certainly notable this week to hear that Guardiola sought the counsel of Sir Alex Ferguson and Arsene Wenger before deciding his next move. Self-interest might have been at work but, as managers who so value their autonomy, it can be suspected that both Ferguson and Wenger relayed their reservations about the structure at Chelsea.
"There is a big salary that comes with the job but also the understanding that you could be relieved of the post at any time," Ray Wilkins, the former assistant manager said. "In my case, it was 'crash, bang, wallop and off you go'. That's the way he works. Guardiola may well have decided that he didn't want to be in a situation like that."
The Abramovich decade can be broadly divided into two parts. The first, lasting into a fifth season, was relatively stable and certainly fruitful. Claudio Ranieri, the so-called 'dead man walking', may feel aggrieved by his treatment but he was never an Abramovich appointment and was replaced by Jose Mourinho, who, won five trophies in three years.
In the following five seasons six managers won another five trophies. The argument, however, that changes in manager have been justified by continual silverware is flawed. In 2006, Chelsea had put themselves in a position to dominate under Mourinho but blew it. Manchester United, Manchester City, Real Madrid, Barcelona and perhaps Bayern Munich have all overtaken them. As Di Matteo demonstrated at the end of last season, subsequent successes have hinged on an existing, but exceptional, spine of players - Didier Drogba, Frank Lampard, John Terry, Ashley Cole and Petr Cech - and have been achieved in spite of, rather than because of, managerial upheavals.
With the Champions League finally in their trophy cabinet, the irony is that there has never been more uncertainty or negativity surrounding Abramovich's Chelsea.
The manager's position remains in a familiar state of flux. The squad are undergoing some necessary and (in the case of Lampard) some baffling upheaval. It certainly seemed instructive yesterday to hear Benitez turn to the reassuring experience of Terry when he had previously indicated that the captain would miss tomorrow's match against Arsenal with his knee injury.
"It's important to have players with character on the pitch if you want to manage a game," Benitez said. "It's difficult to say what a leader is. It's something that happens. We have a group of players with quality and sometimes we miss these things. He's one of the strong characters."
Another thing that could help is changing the atmosphere at Stamford Bridge. A combination of Benitez's past association with Liverpool and outrage at the treatment of Di Matteo has ensured a disharmony among fans that, according to the Chelsea Supporters' Group, is "tearing the club apart". Those tensions have contributed to two defeats and a draw in the past three home games, with Benitez yesterday making his usual pre-match appeal for unity.
Abramovich has not, thus far, been the direct focus for unrest but he is under more risk of personal vilification than ever before.
The question now is how the club restore their image, not just in the eyes of supporters, but to prospective employees around the world.
Abramovich is still known to crave a style of football that would give Chelsea an identity similar to Manchester United, Arsenal and Barcelona. He should be attracted by the work of Jurgen Klopp, Diego Simeone, Michael Laudrup or Joachim Low. Yet has he learnt the lesson of the Andre Villas-Boas experiment, that implementing a revolution in style while overhauling a squad requires patience?
"There are two sorts of reaction: either you stick to your project and the people who are part of it, or you want immediate success," Villas-Boas said. "In that case, you have to change everything. At Chelsea, I think another sacking is just like any other day at the office."
That might be so, but the price Chelsea risk paying for their owner's style is perpetual limbo and a declining ability to attract the world's best managers and players.
Roman's controversial rule at Chelsea:
England coach Sven-Goran Eriksson called at his London house for tea while speculation raged over the future of Chelsea manager Claudio Ranieri.
Splashed pounds 31?million on Andriy Shevchenko from AC Milan. The striker scored nine goals in a three-year stay.
A fractious relationship with Jose Mourinho ended with the Portuguese coach leaving Stamford Bridge despite having won the Premier League twice.
Pushed through the pounds 50?million signing of Fernando Torres, who has supplied just 14 goals in 68 appearances.
Sacked Carlo Ancelotti a year after the popular coach had guided Chelsea to their first League and FA Cup double.
Sacked Andre Villas-Boas after less than a season.
Sacked Roberto Di Matteo, who had taken the club to their first Champions League triumph months earlier.
Upset supporters by appointing the deeply unpopular Rafael Benitez as interim manager