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AC Milan Legends: Paolo Maldini 

Paolo Maldini is the one of the footballers who personally defined loyalty in football, especially at the time when it was more about chasing trophies or money rather than pure love of the game. Of the six greats who played out their entire career in the red and black, he is the longest-serving among them with a quarter-century of immeasurable greatness both on and off the pitch. 

At the age of 16, he made his first-team debut on January 20, 1985, away at Udinese, where manager Nils Liedholm had brought him on to replace Sergio Battistini at half-time. The following season saw him inherited the number 3 shirt from his father Cesare and began his extensive career with the Rossoneri. 

The versatility contributed to his longevity on the turf. Having started as a left-back, he developed his game as a Centre-half as his career progressed, which enabled him to inherit the captain’s armband from Franco Baresi upon his retirement in 1997. 

Apart from the former World Cup Winner, he was integral to the backline of Milan, an immovable selection during which he teamed up with the likes of Alessandro Costacurta, Mauro Tassotti, Cafu and Alessandro Nesta, among others. 

Having easily rejected transfer moves, he remained in the Lombardian capital until he hung up his boots in 2009, aged 41. During which, he played under several managers, most notably winning alongside Arrigo Sacchi, Fabio Capello, Alberto Zaccheroni and Carlo Ancelotti. 

The loyalty was immense that the club had his number three shirt retired, only to be worn again by one of his sons in the future. 

Among those unsurpassable records, Il Capitano has played the most games (902 in all competitions, scoring 33 times) and won the most trophies, more than any other player in the club’s history. 

Inside his trophy cabinet are the following: Eight Scudetti, Five European Cups, Five European Super Cups, Five Italian Super Cups, a pair of Intercontinental Cups, a Coppa Italia and a Club World Cup. 

Also, he enjoyed individual accolades as well, winning the 1994 World Soccer Player of the Year and placed third in the Ballon D’Or Twice. In addition, he was part of Pele’s FIFA 100 list of the greatest living footballers in 2004. 

Paolo Maldini’s legacy goes beyond the pitch, as shown on his return to Milan as a sporting, then becoming its technical director, during which his transfer moves were vital in their Scudetto conquest in 2022