The crushing system is crucial in the virgin olive oil (VOO) mechanical extraction process. The use of different crusher machines can highly influence the quality of the final product, mainly due to the phenolic and volatile content responsible for VOO sensory and health properties. An experimental investigation was conducted to evaluate the effect of the geometric features of a new model of crusher machine for olives. The crusher machine consists of interchangeable rotors: a rotor with hammers and a rotor with knives. The evaluation was carried out with the same fixed grid in stainless steel with 6 mm diameter circular holes. An evaluation was carried out on the impact of the crusher tools on the pit particle size and on the distribution of energy and temperature. The performance of the plant was also assessed in terms of process efficiency and olive oil quality. The results showed that the specific energy released by the tool per unit of product, calculated through both energy conservation and comminution theory, is about 25–27% higher in the case of hammers. Since the impact energy is mainly dissipated in the product as heat, the temperature reached during milling operations with the hammer crusher was also higher by the same percentage with respect to the knife crusher. This has important consequences on the quality of the product: the new knife rotor used in the crushing phase produced an improvement in VOO quality, relating mainly to sensory attributes and the health-enhancing properties of the final product. The ability of the crusher to break cell walls and vacuoles, thus releasing the oil contained therein, is comparable for the two different rotors.