Ancelotti leaves Milan after eight years at the San Siro
By Phil Dawkes
If you want to understand why Carlo Ancelotti was at the top of Chelsea's managerial hit-list, look no further than the big trophy with the jug ears.
Chelsea owner Roman Abramovich took control six years ago and at times the Russian must have felt his pursuit of the Champions League trophy was jinxed.
How else to explain four semi-final defeats and, most miserably, the 2008 final when Chelsea were a John Terry penalty away from claiming the trophy for the first time in their history?
"The Champions League is the holy grail for Abramovich," John Foot, author of Calcio: A History of Italian Football, told BBC Sport. "That is the problem with someone like a Chelsea; third place in the league and an FA Cup is a failure.
"They've come so close in Europe and that is the idea behind getting Ancelotti: he's successful on the European stage."
Ancelotti's eight-year stint in Milan ended when he announced his contract was terminated by mutual respect on Sunday.
And he was duly confirmed on Monday morning as the new manager at Stamford Bridge, on a three-year contract.
His spell at the San Siro has been characterised and arguably facilitated by his achievements in the Champions League.
He has twice ended a season sat on the shoulders of his players, tossing Europe's most famous trophy skyward in celebration.
In 2003 Milan overcame Italian rivals Juventus 3-2 on penalties following a 0-0 draw after extra-time at Old Trafford. Four years later, in Athens, two goals from Pippo Inzaghi helped them to overcome Liverpool.
ANCELOTTI MANAGERIAL SUCCESS
1995/96: Leads Regianna to Serie B promotion in his debut season as a manager
1996/97: Finishes second in Serie A with Parma
1999/2001: Successive second place Serie A finishes with Juventus
2002/03: Wins the Champions League and Coppa Italia with Milan
2003/04: Leads Milan to the Serie A title
2006/07: Wins the Champions League for a second time and the Club World Cup with Milan
The 2007 victory was extra sweet for Ancelotti as it came at the expense of the side that had famously come back from a 3-0 half-time deficit against Milan in the 2005 final to claim the trophy on penalties.
Clearly, Abramovich envisages a not-too-distant future whereby the Italian is sat atop John Terry, Frank Lampard et al joyfully juggling a blue ribbon-clad trophy that finally confirms Chelsea's footballing conquest of the continent, along with their manager's unprecedented hat-trick of Champions League titles.
While the brace of European triumphs are central to Ancelotti's appointment, he clearly has other qualities Abramovich feels are suited to shaping Chelsea's future.
"He's extremely experienced with managing a big club and dealing with big stars," says Foot. "He's a good man manager, very good at reading a game and he is a very fair character.
Foot goes so far as to suggest Ancelotti's sides are similar to Arsene Wenger's Arsenal.
"His teams keep the ball on the ground and play a possession, passing game, which is what Abramovich seems to have been looking for since Mourinho went."
At their best, his Milan sides are a joy to watch; harnessing movement, excellent close control and intricate, accurate passing in a fluid offensive style.
I think the quality that most shines is that he's a tremendous man manager, he knows how to handle superstars.
Many forget prior to Liverpool's stunning comeback in the 2005 Champions League final they were played off the park by Ancelotti's Milan.
Likewise Milan served up a devastating performance to crush an awestruck Manchester United in the 2007 Champions League semi-final second leg at the San Siro, after the Italian side lost the first-leg 3-2.
BBC Radio 5 Live pundit Gabriele Marcotti is confident the 49-year-old Ancelotti will be able to make the transition to the Premier League.
"A lot of the stereotypes about English football are just that; it's not like you're going to go take on a bunch of 10-foot thugs who are going to kick lumps out of you.
"The game is a lot less homogenous than people realise these days and the differences are becoming fewer and fewer between different nations.
"There'll be an adjustment period but there's no question he can do it."
Since former Chelsea manager Jose Mourinho took over at Inter Milan last summer, Ancelotti has been given a glimpse of the mind-games top Premier League managers go in for. However, Ancelotti is no Mourinho.
"He's someone who doesn't particularly like talking to the press," says Foot.
"He's a strong person but not someone who is particularly interested in talking about himself and I would have thought his relationship with other managers would be on a very sociable level."
That is not to say Ancelotti, who has apparently been learning English and is at roughly the level Fabio Capello was when he took the England job, is a soft-touch.
"There's an edge to Ancelotti which perhaps isn't always apparent, but it would be a big mistake to assume he was a push-over and Mr Nice Guy," said Marcotti.
Given the influence AC Milan owner Silvio Berlusconi holds at the club it will be interesting to see how Ancelotti will operate under Abramovich.
At Milan, Ancelotti was required to fit players bought for him by the club into a structure capable of producing attractive football while also earning results.
During his tenure Ancelotti was given the ageing Brazilian trio of Rivaldo, Ronaldo and Ronaldinho, players he did not need, but offered no dissent, instead focusing on how to make it work.
Ancelotti has won the Champions League twice as a manager
Having played under Nils Liedholm at Roma and Arrigo Saachi at Milan, Ancelotti began his coaching career at Parma (1996-1998) where he liked to operate with three at the back and was rewarded with a second place Serie A finish. In 1998 Ancelotti moved to Juventus, where he failed to take the club to the scudetto on two occasions only by the narrowest of margins.
At Milan, Ancelotti's tactical nous brought the best out of midfielder Andrea Pirlo, a player of immense attacking quality and promise, but who at the beginning of the 2002 season was languishing in the reserves.
At that time Milan had an attacking quartet of Rui Costa, Clarence Seedorf, Rivaldo and Shevchenko, but Berlusconi took a shine to Pirlo and wanted him in the side.
With only Gennaro Gattuso as a defensive option in the centre of the pitch, Ancelotti hit upon the idea of playing Pirlo as a deep-lying midfielder, transforming him into a World Cup winner.
"That was one of Ancelotti's greatest moments of genius," says Marcotti. "On paper it was a ridiculously attacking side but he found a way to balance it out.
"The only way you do that is to go to your star players and say, 'guys you have to work really, really hard if you all want to be on the pitch at the same time'."
If you've got a criticism of Ancelotti it's that he's found it very difficult to get rid of the old guard and bring in young players.
John Foot, author of Calcio: A History of Italian Football
Before two serious knee injuries put paid to Ancelotti's playing career he was a tough-tackling, no-nonsense midfielder with Parma, AS Roma and Milan.
In five seasons with Milan he played alongside the superstar Dutch trio of Ruud Gullit, Marco van Basten and Frank Rijkaard, and won the scudetto twice and back-to-back European Cups.
Subsequent experiences managing the likes of Zinedine Zidane, Ronaldo and Kaka have enhanced his ability to connect with big-name players.
As one Milan insider told BBC Sport: "He's a kind, pleasant man, but with great experience of working with champions and that gives him a lot of credibility with the players.
"I wasn't surprised he became a successful coach. He was always a leader on the pitch."
Ancelotti was a hard-tackling midfielder who played 26 times for Italy
The overwhelming characteristic of Milan's squad is that of experience, as is Chelsea's roster. The question is, can Ancelotti develop new young players, a frequently stated aim of Chelsea chief executive Peter Kenyon?
"If you've got a criticism of Ancelotti it's that he's found it very difficult to get rid of the old guard and bring in the young players and that's been Milan's problem, a lack of renewal," says Foot.
"He's someone who is used to dealing with a team that's already there, or buying in outside talent, not someone who's going to bring through young players."
Still, if Ancelotti is required to work largely with what he has got, you won't hear the Italian complaining; it's not his style.
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