After eight years with the unpredictable Italian Prime Minister, Silvio Berlusconi, as his boss at Milan, Carlo Ancelotti is clearly adept at handling pressure. It is a quality he is going to need in abundance at Chelsea.
Ancelotti arrived at Chelsea in the summer charged by the owner, Roman Abramovich, with the minor task of delivering the coveted Champions League crown for the first time in the club's history.
Two years ago, the chief executive Peter Kenyon suggested Chelsea need to win the Champions League twice before 2013 if they are to fulfil Abramovich's ambitions – which basically means Ancelotti has to win it twice in the next four seasons if he is to meet the deadline. No pressure there, then.
Chelsea have reached the semi-finals five times in the six years of the Abramovich era, but have yet to close the deal and take the major prize. Ancelotti has, by way of contrast, led Milan to two Champions League titles, one of only four managers still in the business who has won it more than once. Ancelotti guided Milan to Champions League victories in 2003 and 2007, plus the unforgettable defeat in the final at the hands of Liverpool in 2005.
On the surface it looks like a marriage made in heaven. The man with the Champions League Midas touch coming to the club who just can't quite manage to claim the ultimate prize. Since Abramovich arrived in 2003 he has overseen a catalogue of narrow misses in Europe, a trophy that has proved beyond the managerial powers of Claudio Ranieri, Jose Mourinho, Avram Grant, Luiz Felipe Scolari and Guus Hiddink.
Ancelotti's league record at Milan has been relatively modest, with just one Serie A title in eight attempts but it is his undoubted brilliance in Europe that has convinced Abramovich to stump up £6.5m a year for his services.
Ancelotti yesterday spoke at the club's Surrey training ground of what he expects from his players, given the importance the club have put on conquering Europe's greatest prize.
In one breath he suggested there was no greater urgency to gain Champions League glory; then in the other he made it clear that reaching the final in Madrid in May 2010 was the minimum requirement he expects from his players.
"The first objective is to arrive at the final, not to win it. It's not easy but we have the possibility to do this," Ancelotti said. "It's not that the club asked me to win the Champions League. They asked me to win the Champions League, Premier League, FA Cup, Carling Cup ... this is a joke."
It was immediately pointed out to Ancelotti that Chelsea have won all the other trophies, but not the Champions League. The Italian insisted, however, that when he met Abramovich last summer, and the year before, to discuss the Chelsea job, no mention was made of the Russian oligarch's lust for the Champions League. "We didn't speak about winning the Champions League. Roman chose me as a coach because he liked how my last team, Milan, played," Ancelotti said.
The Champions League has been described as the Holy Grail that Abramovich craves. That may be going too far, but it certainly irks one of the richest men in the world that this trophy has so far proved the one thing his money cannot buy.
Chelsea have been very close in recent years, so close in fact that mental scars from their years of failure must be a concern. Ancelotti dismissed the suggestion yesterday, saying: "I don't think there is a psychological problem. Chelsea went very close to winning it. They didn't but I repeat, there is a real possibility we can do very well this season."
If John Terry had scored that penalty in Moscow in May 2008, the whole picture would be different. But he slipped, missed and Manchester United – not Chelsea – won the first all-English final. And had the referee Tom Henning Ovrebo given one of those blatant penalties against Barcelona in last season's semi-final, it could have all been so different.
At least Ancelotti has mostly good memories of European football's elite competition, in contrast to Chelsea stalwarts like Terry and Frank Lampard, for whom the chase to win the Champions League is in danger of becoming a burden rather than a joy.
However, if Abramovich believes Ancelotti is the possessor of a rare secret that can unlock European glory, he is likely to be sorely disappointed by the Chelsea manager's answer at yesterday's press conference.
Asked what is required for Chelsea to take the ultimate step and win the Champions League, the coach said: "I don't know. Chelsea have had a very good result in the Champions League because they arrived five times in semi-finals in six years. It's not easy to do that. To win the Champions League is very important. You need a bit of luck to win it as well. But it's not only luck. You have to believe to be the best in this competition."
Double nor quits: Dual-winning coaches
*14 coaches have won the Champions League twice. Four are still working:
Ottmar Hitzfeld (B Dortmund 1997, B Munich 2001) Beat Juventus before win over Valencia four years later.
Sir Alex Ferguson (Man U 1999, 2008) Injury-time win against Bayern before last year's penalty drama with Chelsea.
Vincente del Bosque (R Madrid 2000, 2002) Success over Valencia then beat Bayer Leverkusen at Hampden.
Carlo Ancelotti (Milan 2003, 2007) Shoot-out success over Juventus, preceded revenge over Liverpool.Reuse content