In his early career, he played for several clubs around the Buenos Aires area, during the amateur era in Argentine football, most notably Chacarita Juniors.

This excellent River Plate team included two young players who would become legends of the game Adolfo Pedernera and José Manuel Moreno.

The team was coached by the Hungarian Emerico Hirschel, who had a big influence on Cesarini and his teammate Carlos Peucelle, which would be put to use in the 1940s as they took charge at the club.

From 1941 to 1947, this River Plate team achieved legendary status: Cesarini was coach from 1941 to 1944 when the level of football was such that they became known as La Maquina (The Machine); the forward line of Moreno, Pedernera, Munoz, Labruna and Loustau is considered to this day to be the greatest seen in South America.

River won Argentine league titles in 1941, and 1942 under La Biblia del fútbol as Cesarini became known for his authority on all matters pertaining to the sport.