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?
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.
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.
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 etc all 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.
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.
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.
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.
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.
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.
Subsequent experiences managing the likes of Zinedine Zidane, Ronaldo and Kaka have enhanced his ability to connect with big-name players.
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?
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.
