In 1856 Vasquez was rustling horses. A sheriff's posse caught up with him near Newhall, and he spent the next five years behind bars in San Quentin prison. There he helped organize, and participated in, four bloody prison breaks which left twenty convicts dead. By 1866 he had committed numerous burglaries, cattle thefts, and highway robberies in Sonoma County. He was captured after a store burglary in Petaluma and sent to prison again for three years. His "trademark" was "binding victims' hands behind their back and leaving them face down in the dust."