Leonardo played for AC Milan for four years between 1997 and 2001 and for a short spell in 2003. The Brazil international slotted in to the team as a trequartista and played a critical role in the resurgence of Milan and their Scudetto run in 1998/99. Leonardo joined Milan after an amazing run in France, Brazil and Japan including winning the World Cup in 1994.
Leonardo will always be remembered for transforming the role of the trequartista with Milan. His flair and versatility made him the total attacker capable of swapping the wings for the central attacking midfield role and specifically being able to pull out defenders creating pockets of space for the likes of George Weah, Oliver Bierhoff and Andriy Shevchenko over his years. Leonardo was an elegant player who was great at creating chances and created numerous key assists over the course of his Milan tenure. He played an extremey important role in getting the club back on track and going all in for the Scudetto, he was also principally responsible for allowing key attackers to flourish at the club. One of Leonardo's best traits was his clinical touch from set pieces with his pinpoint accuracy as he helped out the team numerous times from dead ball situations when all else was deadlocked. Leonardo paved the way for Kaka to succeed as he created the mould for the position.
Achievements with Milan
- Serie A : 1998–99
- Coppa Italia : 2002–03
One of Leonardo's finest performances came in the Scudetto winning season in 1998/99 when he single handedly saved Milan for a derby loss to Inter Milan when he scored a brace for a 2-2 draw. Leonardo fine display from the right wing went a long way in supporting Milan's return for the mid-table to lift the Serie A title. Watch the highlights of his brace here or below.