Should Carlo Ancelotti become Roman Abramovich's sixth manager in as many years at Chelsea he will arrive with three important qualifications. He has won the Champions League twice as a player (in its original incarnation as the European Cup) and twice as a manager, he is used to accommodating an interfering owner, and he has an even temperament.
That last quality has proved invaluable while managing Milan. Ancelotti's latest dispute with Silvio Berlusconi looks to be terminal but the 49-year-old has not survived eight years in one of the hottest of management positions – there had been seven coaches in five seasons prior to Ancelotti – without knowing when to appease the grandstanding Prime Minister of Italy, and when to hold his ground.
The issue that has vexed Berlusconi most about Ancelotti is also the one part of his CV that does not fit the Abramovich wish-list. Berlusconi has regularly demanded his team play more attacking football. As Milan are effectively an advertisement for Berlusconi's aggressive, can-do approach to politics, he desires a team that wins hearts and minds as well as trophies. Abramovich is less inclined to make regular pronouncements in the press but his coterie of advisers has made it clear he wants to see entertaining football of a nature which neither Jose Mourinho, Avram Grant, Luiz Felipe Scolari nor Guus Hiddink consistently produced. Indeed, none has presided over as entertaining a team as Claudio Ranieri, the coach Abramovich inherited.
Sometimes Ancelotti paid attention to Berlusconi, sometimes he did not. As Ancelotti once said: "In the end it has to be the coach who decides. And it is important the players understand it is the coach who decides. Mr Berlusconi understands this perfectly well." Which perhaps explains why Berlusconi would often as not conduct his diplomacy in the media, knowing the fans (and voters) would be on his side even if the manager disagreed.
Not that Ancelotti is wedded to a defensive game. There has certainly been no shortage of flair in his team. The current squad includes Kaka, Ronaldinho, Clarence Seedorf, Alexandre Pato and Andrea Pirlo. Plus, of course, David Beckham and Andrei Shevchenko. The latter's return is a clear example of Berlusconi's interference, and his absence from the team-sheet an equally obvious indication of Ancelotti's determination to stand by his own judgement. As important as any of the above, however, have been defenders like Paolo Maldini and Alessandro Costacurta, and midfielders like Gennaro Gattuso. Milan have always had a balanced side and, aside from a crazy 15 minutes in the European Cup final against Liverpool in Istanbul four years ago, been hard to break down.
The same can be said of the great Milan team Ancelotti played in which has clearly influenced his management philosophy. Arrigo Sacchi, who later hired Ancelotti as an assistant to the Azzurri at the 1994 World Cup, had players of outstanding skill, such as Marco van Basten and Ruud Gullit, but also a team with a formidable work-rate and pressing game.
Ancelotti's midfield partnership with Frank Rijkaard was a key aspect of the team but it is the Dutchman and his compatriots who people think of when they remember that team. Not that Ancelotti appears to mind. He keeps an equally low profile as a manager. He does the press, but he does not seek attention in the way Mourinho does. Inevitably, like everyone else in Italy, he has been irritated by Mourinho even before the latter took over at city rivals Internazionale. Mourinho's previous touting for the Milan post prompted Ancelotti to say: "Is Mourinho up for my job? If we'd known earlier we could have found him a job. Helping the goalkeeper coach? No, he's never played football, he wouldn't be capable of shooting on goal." Mourinho responded: "My dentist is great, even though he's never had a toothache."
Ancelotti also noted he had won two Champions league titles, but that did not make him "special". He has won much else besides, but was once known in Italy as "un perdente" – a loser. This followed three second-place finishes in Serie A, first with Parma, which was respectable, then twice with Juventus, which was not. The first, in 2000, was the afternoon when Juve's match at Perugia was interrupted by a downpour. When referee Pierluigi Collina demanded that it resume, with most fans having gone home, Juve conceded to hand Sven Goran Eriksson's Lazio the title. Juve fired Ancelotti but Berlusconi, searching for stability, had been impressed. In his second season he delivered the Champions League, defeating Juventus on penalties at Old Trafford. In his third, the title. It is, though, Milan's only Serie A success in his eight seasons, which is as good a reason as any for him to exit
If he does move he will have to leave his base of many years. Born in Emilia-Romagna, he has spent most of his life in and around Parma raising a family which includes 19-year-old Davide, who was on Milan's books as a youngster but now plays in Serie D. Famously Davide once attended a press conference at which Ancelotti was being asked about signing Jaap Sam. Father denied everything until Davide said: "But Dad, why don't you want Stam, you're always talking about him?" The son is understood to be a big fan of English football, so much so that Carlo would consult him about Premier League players. Davide may have been receiving plenty of phone calls recently.
Milan's success in 2003 made Carlo Ancelotti only the fifth person to win the European Cup as both a player and as a manager.