Things to Know:
D’Alessandro was born in the La Paternal section of Buenos Aires, Argentina. He joined the labor force as a pizza delivery boy before becoming a professional footballer. Known as El Cabezón (“The Big Headed”) for how large his big head looks on his small frame rather than any ego connotations, he emerged through the River Plate youth system that has produced much of Argentina’s top talent over the years. He followed the likes of Santiago Solari and Pablo Aimar through the ranks, together with Javier Saviola, with whom he shared the limelight in the 2001 Youth World Championship. With the River Plate senior team, he won the 2001–02 and 2002–03 Primera División titles. D’Alessandro attracted attention from European clubs following his success and performances at the 2001 FIFA World Youth Championship so in 2003 he moved to Europe where he played for 4 years. After San Lorenzo and Internacional he he returned to River Plate after 12 and a half years on a loan deal. He won his second Recopa Sudamericana and the Copa Argentina during his stay at the club.