Legendary Teams: Ancelotti's AC Milan set a high standard as European conquerers
MEN'S
Gregory Caltabanis
3 Yrs Ago
AC Milan may have only won one Scudetto under Carlo Ancelotti, but few teams, if any, rose to the occasion on the European stage as consistently as his Milan sides did. As Adriano Galliani put it, the club’s former vice-president, the Champions League is in AC Milan’s DNA.
When Carlo Ancelotti was appointed by AC Milan in 2001, few expected the Italian tactician to lead the Rossoneri back to the pinnacle of European football, let alone twice. Juventus had just sacked him after a disappointing stint in charge while Milan were just coming off a trophyless season of their own under Fatih Terim.
Ancelotti built his side around Andrea Pirlo, deploying the maestro from a deeper role for the first time in his career. With Gennaro Gattuso acting as the Rossoneri's hardman and Clarence Seedorf roaming dangerously in the final third, Milan's midfield proved to be an equal match for any competitor.
Milan marched to the Champions League final in 2003 behind a backline anchored by Paolo Maldini and Alessandro Nesta, beating the likes of Real Madrid, Ajax and fierce rivals Inter.
Ancelotti's AC Milan teams were tactically versatile, armed with a well-balanced midfield and a world class rearguard. The Rossoneri were equally comfortable sitting deep and inviting pressure as they were dominating the proceedings on their own. Rui Costa, the side's attacking midfielder in Ancelotti's trademark 4-3-1-2 setup, was responsible for tying it all together in the final third.
AC Milan narrowly overcame Juventus in an all-Italian stalemate, winning its first Champions League title in nine years. This was only the beginning of Ancelotti's dynasty at Milan.
Fresh off their Champions League success, the Rossoneri signed Kaká from São Paulo and promptly introduced him into the fold in place of Rui Costa. The trequartista position was integral to Ancelotti's setup and could not go unaddressed, and Kaka filled it like few players ever did.
Kakà wasted no time connecting with Milan's front two and formed a deadly partnership with Andriy Shevchenko. AC Milan did not miss a beat with the Brazilian in the hole, claiming their 17th  Scudetto.
The Rossoneri had previously struggled for consistency under Ancelotti, but managed a historic season, only losing twice in domestic play all year. After failing to defend their Champions League title, Milan returned to the final the following year.
AC Milan got off to a great start in the final, notching three first-half goals against their English counterparts. The second half, however, was a completely different story with Ancelotti's men inexplicably conceding three goals in six minutes. AC Milan eventually lost in penalty shoot-outs, culminating in one of the toughest defeats in the club's history.
"I thought about quitting because, after Istanbul, nothing made sense anymore," said Pirlo. "They had mentally destroyed us. It only got worse as the hours went on. Insomnia, rage, depression, a sense of nothingness. We had invented a new disease: The Istanbul Syndrome." 
Like any great team, AC Milan picked itself up after the defeat and went back to work. Ancelotti shook up his side with Shevchenko leaving for Chelsea, deploying Kaka and Seedorf in support of Inzaghi. In many ways, Milan's ability to improve even after notable departures is what separated them from their counterparts.
The switch gave Milan newfound life, with the Rossoneri dispatching Bayern Munich and Manchester United on their way to a highly-anticipated rematch against Liverpool in the 2007 Champions League final. This time around, Ancelotti's men made no mistake.
Inzaghi notched a goal on the stroke of halftime and doubled his tally with less than 10 minutes to play. Dirk Kuyt's consolation header right before stoppage time gave the Rossoneri painful flashbacks from just two years earlier, but it wasn’t enough to stop Milan this time. The revenge mission was officially complete.
Ancelotti's AC Milan claimed its second Champions League title in four years with the win, while the loss in the 2005 Champions League final might have put a dent in the dynasty, Ancelotti’s AC Milan side remains one of the best in history.
Presenting Sponsor
Official Sponsors
International
Champions Cup