Silvestre first saw action in 1890 at the age of 19 in a skirmish as a cadet against the "Mambises" guerrillas seeking independence in Cuba. In February 1895, a full-blown rebellion broke out in Cuba, known as the Cuban War of Independence. After he attended the academy, Silvestre returned to Cuba in 1895 to fight against the "Mambises" until the Spanish lost the 1898 Spanish–American War in which he received 16 wounds altogether and received a severe incapacity of the left arm that he disguised very well. During his time in Cuba, the aggressive Silvestre had a marked preference for cavalry charges and fighting hand to hand against the "Mambises" and was widely liked and respected by the men under his command.