The paper investigates the optimality of the handbrake cornering, a strategy widespread among rally drivers. Nonlinear optimal control techniques are used to mimic real driver behavior. A proper yet simple cost function is devised to induce the virtual optimal driver to control the car at its physical limits while using the handbrake technique. The optimal solution is validated against experimental data by a professional rally driver performing the handbrake technique on a loose off-road surface. The effects of road surface, inertial properties, center of mass position, and friction coefficient are analyzed to highlight that the optimality of the maneuver does not depend on the particular vehicle data set used. It turns out that the handbrake maneuvering corresponds to the minimum time and minimum (lateral) space strategy on a tight hairpin corner. The results contribute to the understanding of one of the so-called aggressive driving techniques.