Sir Alex Ferguson has counted them all in and out – those Chelsea managers hired by Roman Abramovich to confound him and leave him down in the dust. But now, to the list of those whom he has seen off, arrives a name to send a shiver even down his spine. Carlo Ancelotti, "Carletto" to his former Milanese team-mates, was the manager whose Milan side gobbled up Manchester United – Wayne Rooney, Cristiano Ronaldo and all – in the San Siro in the 2007 Champions League semi-final and then spat them out. Not an experience for a Scottish pensioner to forget in a hurry.
Rafael Benitez's reflections will differ, of course. He has that balmy Istanbul night of 2005 to reflect on and Liverpool's Champions League defeat of Milan – an occasion which will be matched by none other in either managers' life. But the overriding point is that Abramovich has hired an individual who has journeyed liked few others to the grand finals of the one competition which has so eluded him.
When Ancelotti took the reins at Milan, the club were not in great shape. His fourth place in Serie A that season (2001/2) was considered an achievement. There was to be but one Serie A title in the seven years that followed, in 2004, and a single Italian Cup to add to the sum total of serious silverware after 11 years of work in Italy. But it was in Europe that he conquered: two victories, that 2005 final defeat, a quarter and semi-final in other years. Milan never perished before the last 16 under Ancelotti's guidance.
Though he also has the 2005 win over the reigning Premier League champions to encourage him into that first United fixture, an individual in the Ferguson, or Jose Mourinho, mould he is not. His mild and low-key demeanour has contributed to his ability to persevere at Milan under the intrusive gaze of Silvio Berlusconi. The telephone calls from Berlusconi between games, seeking team news and offering his opinions, have been tolerated and indulged where possible, Ancelotti demonstrating his ability to manage a club in the widest meaning of the phrase.
And he has known where to draw his own lines in the sand, too. Berlusconi insisted on the hiring of Andrei Shevchenko and Ronaldinho for this season but Ancelotti allowed the former 16 Serie A starts and the latter just two. The proven ability to manage a club on the high seas will be useful at the eternally tempestuous Bridge.
Abramovich is not indisposed to that kind of interference himself – witness Chelsea's own signing of Shevchenko – though after the seven years he has known at San Siro, Ancelotti will find the Russian's approach to be positively laissez-faire. The major unanswered question is how his modest achievement in Serie A will have prepared him for the Premier League – a competition of higher standards and tempo. Ferguson will undoubtedly take supreme delight in exposing any deficits.Reuse content