A famous NBA player once said in an interview that failure is part of sports, but it's an overused concept. "Michael Jordan played for 15 years and won six NBA titles. Does that mean the other nine years were a failure?". Paolo Maldini also said of himself that he was the most losing player in history: "I've won a lot, but I've also lost a lot".
Can we confidently include Carlo Ancelotti in this lineage? After hanging up his boots in 1992, he assisted Arrigo Sacchi during the American World Cup. He then began his coaching career close to home, first in Reggio Emilia with Reggiana in Serie B, where he finished fourth and secured promotion to Serie A, and then two years at Parma, achieving a historic Champions League qualification in his first year and sixth place in his second year.
From there, he moved to Juventus, a challenging environment for a Milanista icon. He still managed to secure two second-place finishes. In 2001, Ancelotti's career took off: his eight years at Milan became the hallmark of an unbeatable and cohesive team: one league title, two Champions League titles, one Coppa Italia, one Italian Super Cup, two European Super Cups, and a Club World Cup.
After leaving Milan, Ancelotti went to Chelsea and won the league and FA Cup in his first year, then to Paris, where he won the league in 2012/13. He joined Real Madrid, winning the Champions League and Copa del Rey in his first year. Then, in 2016, he went to Germany, where he won the league but was dismissed early in his second season. Returning to Italy with Napoli, he inherited a team at the end of its cycle after Sarri's exceptional three years, yet he led them to second place and the Europa League quarter-finals. After being sacked in December 2019, he signed with Everton in England, where he didn't shine.
After two underwhelming seasons, Florentino Perez called him back to lead the Blancos, and he excelled: winning the Champions League and the league in his first year again; the Copa del Rey in his second year, and another double last year with the Champions League and the league.
Is he the greatest of all time? Yes, definitely.