A strong, hard-working, dynamic, energetic, and gregarious team player, Fortunato was known for his pace, class, stamina, determination, and tactical intelligence as a footballer, which enabled him to cover the left flank well and win back possession effectively. He also had a good left foot and was known for his crossing accuracy from the touchline, and ability to beat opponents, make attacking runs down the wing, and deliver balls to teammates in the area. Although he played at left-back throughout his professional career, or as an attacking wing-back, he was a highly versatile player, who started out playing as a centre-forward and as a left midfielder in his youth, and was also capable of playing as a central or defensive midfielder, as a centre-back, or as a sweeper. A precocious player, he was regarded as one of the most promising young left-backs of his generation in Italy; his playing style was frequently compared with that of legendary former Juventus full-back Antonio Cabrini. In addition to his talent and footballing skills, Fortunato was also known for his calm composure, friendly personality, and strong mentality, both on the pitch and in the dressing room, in spite of his reserved, and introverted character.
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Fortunato’s performances with Genoa in the 1992-1993 season caught the attention of Juventus boss Giovanni Trapattoni, who brought the promising youngster to the Turin club the following season for 12 billion Lire. The left-back was an instant hit, and was awarded the number 3 shirt, which had belonged to former Juventus full-back Antonio Cabrini during the 1980s. Fortunato started his first season with Juventus strongly, and soon became known for his endless running along the flank and his fine left foot, which he would use to provide accurate crosses for the likes of forwards Roberto Baggio, Fabrizio Ravanelli, and Gianluca Vialli. His most important attribute was that he loved being a team player, both on and off the pitch. His charm and great personality won the hearts of many, so much so that former Italy coach Arrigo Sacchi described him as “a revelation of Italian football”, and called the Juventus star to make his one and only international appearance against Estonia, on 22 September 1993, in Tallinn. Fortunato took Paolo Maldini’s place and played alongside veteran and national team captain Franco Baresi in a game that Italy won 3–0. The left-back showed striking similarities to Maldini and he was initially even in Sacchi’s plans for the 1994 FIFA World Cup.