He may think guiding Liverpool into second place in the Premier League or turning around their 2005 Champions League final at half-time have been his toughest tests.
Problems: Rafa Benitez has struggled in the transfer market
But if the manager gets his transfers wrong this summer he will be surely always be Anfield's nearly man.
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The number of poor and overpriced signings the Spaniard has made for Liverpool are too numerous to mention and that is why his squad have failed him at key times.
Liverpool need more depth to win the League and if Benitez gets his player trading wrong again after fighting so hard for more influence over transfers this key element of management will have become his fatal flaw.