2) Carlo Ancelotti
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Arguably one of the most successful and respected managers of all time, Carlo Ancelotti has won the Champions League five times as a player and manager. The Italian manager, set to take over at Bayern Munich prior to the 2016/17 season, won four of those titles with AC Milan.
Player: In a 16-year career as a central midfielder, Ancelotti played for Parma, AS Roma and AC Milan. But it was at the San Siro that he made his mark on Italian and European football. Widely known as the predecessor to the now famous Andrea Pirlo role, Carletto was one of the finest of his era.
He was at his peak during his time at AC Milan and played alongside club legends such as Frank Rijkaard, Ruud Gullit and Marco van Basten. Under the guidance of pioneering manager Arrigo Sacchi, Milan won back-to-back European Cups in 1989 and 1990 – the last side to defend the European Cup/Champions League title.
Manager: Ancelotti has managed top clubs across the continent, ranging from Juventus, AC Milan, Chelsea, Real Madrid and PSG. The Bundesliga will be the fifth different league he will work in – a unique achievement in Europe.
Again, it was at AC Milan where he made his mark. His first Champions League title came in 2003 when his side beat his former club Juventus 3-2 in a penalty shootout at Old Trafford. Although he managed to take Milan to the final in 2005, the ‘Miracle of Istanbul’ saw Liverpool come from behind to win their fifth European title in a penalty shootout. However, Ancelotti would have his revenge in 2007 when Milan got the better of the Anfield side with a 2-1 win.
The Italian manager would then move to newly-rich PSG and find domestic success before helping Real Madrid win La Decima – their 10th Champions League crown – in his very first season at the club.
