Abstract: The expression of virtuality in the Essais, beginning with the program announced in the prefatory “To the Reader”, leads to identify the different shades in Montaigne’s assessment of his past, his own “essence”, and the actions of others. The modalities of potential and counterfactual allow him to join the personal confession, to the practice of a pleasant imagination, and to the accusation of actual misdeeds such as the Spanish colonisation, thus presenting, courteously and daringly, reproach and advice.