Is Peter Crouch a luminary, but only in the way of a lamp-post? Is passing on Michael Owen an error that will haunt the Anfield manager with each new strike on goal for Newcastle by the man who had the door of his old house slammed in his face? How long can the wasteful ways of Luis Garcia be tolerated by a team of the highest class?
They are big questions, whose answers may well shape Benitez's destiny, but they are also intriguing and they are addressed to a man whose football spirit is essentially filled with adventure - and who, in an astonishingly brief time, has changed utterly the horizons of his club.
On that last point the same is true of Chelsea's Jose Mourinho, but they are different - sharply different - horizons.
They stretch no further than the mechanics of winning, or in this case of the Champions' League outing at Anfield, not losing.
Liverpool, denied two strong penalty appeals and one decent ask, should have won the game and virtually guaranteed their progress to the knock-out phase.
But they did have one psychologically important achievement before Sunday's Premiership rematch. They did highlight a certain hollowness at the heart of the Mourinho empire. Chelsea's performance was so lacking in ambition it made utterly redundant the current raging discussion about negative tactical formations.
Mourinho played his version of 4-3-3. But in terms of serious intent to take hold of the game the only relevant number was a big fat zero, and this was clear from the moment Didier Drogba, at £24m maybe the most overpriced player in the history of football, booted the ball into touch straight from the kick-off.
Did the Special One order such an opening statement, and if he did was it a gesture of contempt for all those that say a team of such individual talent has a duty to rise above the functional, albeit a method so refined that almost all opposition is turned to dust? If he did he was recalling the old days of Wimbledon; he was making a comment of derision for all those in the game who still don't quite believe that the end - his and Chelsea's success - justify the means.
And what were these means? Ninety minutes of play from the richest team ever assembled which lacked one moment of authentic attacking glory. Drogba was a disgrace and on either flank the potential brilliance of Arjen Robben and Damien Duff was sacrificed completely to the task of tracking back. The midfield of Michael Essien, Frank Lampard and Claude Makelele was completely sterile. The bug of adventure had plainly been killed off somewhere along the M1.
Does Mourinho or his owner Roman Abramovich care about Chelsea's contribution to the wider values of football? On this evidence plainly not. When Robben, who last season illuminated the method of Chelsea with some stunning accomplishment, gave way to the £21m reserve Shaun Wright-Phillips he was unconsoled by the arm his coach casually placed on his shoulder and this was not so hard to understand. He is a Dutch player bred on the concept of total football that has inspired generations of his countrymen. In Chelsea he is learning another game. Not total football, but minimalist football; football that gives only what it has to, football that makes functionaries of players who cost more than £20m. Yes, players who win or draw when necessary but who do not stretch themselves in expanding the beauty and the range of the game they play.
Expansion of thought and performance is everything in Benitez's new world of Anfield, and the only argument is the fierce one about his personnel. Djibril Cissé does not look the answer, especially when played wide, and the potential of Crouch is one key to the immediate future. Already the beanpole striker has caused division in some erudite football circles. Ian St John, the most vital of front men, is inclined to the belief that if Crouch does have major assets they are currently being well hidden.
St John's contemporary John Giles is of a different view. After his commentary stint for Irish television, Giles said: "Crouch was my man of the man of the match. I don't think we have seen the best of him yet but already he is making a valuable contribution. I would have loved to have seen him operate with Owen, but then Benitez has his opinions and you can only admire the strength of his convictions. He is clearly his own man."
What no one questions is the fact that Benitez is a football man reaching for a new dimension, and his disappointment at not signing the Benfica wide man Simao Sabrosa and his ultimately quixotic faith in the skill of Harry Kewell has to make you wonder how he might try to exploit the gifts of a Robben or a Duff or a Wright-Phillips.
For the moment, Benitez's most convincing statement is his faith in the beautiful play-making of Xabi Alonso. Chelsea have the power and the wealth, a legion of formidable players and a coach of brilliant organisation - and, so far at least extraordinary motivation.
But this week they didn't have a touch of the football angels. In Alonso, this is Liverpool's greatest possession. It would be a thrilling foundation for any club's ambitions.
- More about:
- Chelsea F.c.
- Claude Makelele
- Frank Lampard
- Jose Mourinho
- Liverpool FC
- Premier League
- Real Madrid