In a 16-year managerial career that has taken Carlo Ancelotti from Reggiana to Chelsea via Parma, Juventus and AC Milan, it is doubtful whether he has faced a more momentous or difficult decision.
The equation is simple. If Chelsea do not score at least once against Manchester United tomorrow night, Ancelotti will join Claudio Ranieri and Avram Grant (both swiftly sacked) as the only managers to end a season without a trophy since Roman Abramovich bought the club in 2003.
So, in desperately needing a goal, does Ancelotti select a system and strikers who, between them, impressively set an all-time Premier League record for their attacking play last season? Or does he give another chance to a newcomer who, for both club and country, has now not scored in more than 13 hours of football?
The answer should be obvious but, when the newcomer in question is a £50m investment called Fernando Torres, you get a sense of the dilemma.
Alex Ferguson seems perfectly content to put his £30m striker on the bench in the languid shape of Dimitar Berbatov but, the key difference is, there was unquestionably nobody outside of the managerial dug-out who brought the big money striker in red to Old Trafford. Intriguingly, Ancelotti says that he has already decided on the system that he will employ at Old Trafford and there is a feeling that he will again opt to play both Torres and Didier Drogba in a 4-4-2 formation. That would surely be a mistake.
Both Torres and Drogba look more comfortable as a lone central striker and the evidence of the first leg against Manchester United is that 4-4-2 also does not bring out the best from other key players, notably Frank Lampard and Michael Essien.
Logically, Chelsea's best chance is to revert to their tried and tested 4-3-3 system, with Drogba returning as the main striker.
Since the end of January, Ancelotti has tried just about every combination involving Drogba, Torres, Nicolas Anelka and Salomon Kalou and the return from his four main strikers has been just five goals in 12 games.
A Champions League quarter-final is not the time to compromise or experiment further. The necessary work of eventually evolving Chelsea's style around Torres should now wait to pre-season and some of the remaining Premier League matches.
Yossi Benayoun, who spent three years with Torres at Liverpool, offered a telling insight into how the players have been trying to adapt. "Chelsea are used to playing with Didier, so that means playing up to his body, not playing behind the defenders into the space which is where Fernando wants the ball," he said.
"Slowly, slowly, the players have got to know him better. I think it was hard to get used to his game. I know he didn't score but if you look at most of the games he's played he does have great movement."
On Saturday against Wigan, Chelsea did initially revert to the 4-3-3 formation of last season and, while Drogba showed signs of a return to form, the contributions of Anelka and Florent Malouda were sporadic.
In labouring to a 1-0 win, Ancelotti felt that the players already had Old Trafford "in their minds". Ancelotti also urged his squad to focus on the collective tomorrow night.
"Everyone is trying to resolve this problem we have individually," he said. "Obviously it's better to stay in focus and work more with each other."
Yet Ancelotti agreed that it would be the "character" of his players rather than tactics which would be decisive against United.
"Tactically more or less it is the same game that we played here," he said. "I have to watch the game and prepare something that we can do to create difficulties.
"Mentally you can make the difference. You have to cope mentally with this type of game. You have to use personality and courage. They have to truly believe that we can win there. I don't know if they will be able to do this. But at the start of the game you have to believe."
From Roberto Martinez, there were further words of encouragement, even after Torres had impeded Wigan goalkeeper Ali al-Habsi in the build-up to Malouda's winning goal. "I felt his movement was back," said Martinez.
"It's all too easy for people to say when a striker hasn't scored that he hasn't performed very well. There's a lot of expectation. Fernando had a very tough summer. He won the World Cup, then he had very little rest, he's been injured and it's going to take a bit of time. Fernando Torres is going to turn out be a bargain for Chelsea by the end of his contract."
Martinez might well be right. At only 26, Torres should have a big future at Chelsea. The £50m question for Ancelotti is whether he also represents the best option for the present. (© Daily Telegraph, London)