So far, in his pursuit of his long-held dream of encouraging Spurs cockerel to clear its throat again for one more triumphant crow, he has failed.
Nine managers have so far paid the price in 13 years of Levy’s ruthless stewardship. It would be no surprise if Mauricio Pochettino, the tenth, has started to look at the small print of his contract.
For, worryingly, the only sounds coming out of the Lane now are the boos and jeers of dissatisfied fans – and the noisy demolition of reputations.
Levy sits impassively in the stand at Spurs, staring out like some inscrutable sphinx from his position of power, lauding it over all and sundry with expressionless, dead eyes.
Like those Egyptian images from the land of the Pharaohs, he never shows a flicker of emotion. Few have ever heard or seen him have a conversation in public.
And now there is a growing belief that the man known as the toughest negotiator in football when it comes to buying and selling will either make Tottenham great again, or break them.
This belief seems to be filtering out from the foundations of the club itself, where players are said to be doubting whether there is a way ahead under the current boardroom regime.
According to Tuesday’s Daily Telegraph, Pochettino will hold a meeting with his staff when they return from international duty. The chairman’s role will inevitably be discussed, as will that of the rather mysterious technical director, Franco Baldini, who largely determines which players are signed.
Levy, of course, sacked his most successful manager, Harry Redknapp. Back then, over two seasons, H made the club one of the most attractive in the Barclays Premier League, playing scintillating football orchestrated by Gareth Bale.
Redknapp did not last the course – no explanation was ever offered – neither did Gale, and the money from his transfer, around £85 million, has brought in players who so far have not lived up to expectations.
It is no surprise, then, that the latest occupier of the manger’s chair, Pochettino, is coming under increasing pressure, just like those before him.
George Graham, Glenn Hoddle, David Pleat, Jacques Santini, Martin Jol, Juande Ramos, Harry Redknapp, Andre Villas-Boas and Tim Sherwood were caught in a revolving door policy that has done Tottenham no favours.
All failed and were deemed unsuitable for a chairman, now 52 years old, who has supported Spurs since he was a boy, and brought his expertise in economics, corporate finance and retail management into the club. As for a football background, there appears to be none.
Pochettino has so far not been able to give Spurs what they want, the traditional blueprint of success labelled the Tottenham way.
They have never aspired to anywhere near the football played under Redknapp, and perhaps they never will. If that happens. then Pochettino will go the way of the previous nine who failed to make Levy’s dreams come true.
And then, there is the danger that prospective candidates for the job will be frightened off, because surely the position of head coach has become virtually untenable.
Levy, it appears, doesn’t do patience. What then for Spurs ? They crave to be great again, but so far are a side lacking passion, tactical awareness, hunger and, above all, the ability to win in style.
The players with whom Pochettino has to work are not worth the £85 million forked out on them. How many would Spurs get their money back on? Answers on the back of a postage stamp because the man who once revelled in cut-price deals has, it seems, unwisely paid over the odds for his latest consumer goods.
As always, one person will carry the can, one will be removed from his job, and somebody else brought in. It’s been that way at the Lane since 2001, and it will only ever cease when Levy himself stops wheeler dealing, and another chairman moves in to re-construct the club.
But how bad have Tottenham to become before that happens, and the pressure comes off what now has become a doomed job?
The bad luck for Spurs fans is that there is only one man who knows the answer and he, as usual, is keeping his counsel. Levy’s mantra is action – not words.
PICTURE COURTESY OF: FLIERFY