The article discussesthemilitary career ofthe Englishman Giovanni Aguto, amercenary captain who servedthe Italian city-states of Italy and the Papal States for a long time. Based on the material of the Florentine chronicles the brothers Giovanni and Matteo Vilanni, Marchione Stefani, information reported by anonymous authors, the path from an ordinary mercenary to a famous condottiere and honorary citizen of Florence is shown. The conclusion is made about the inconsistency of the image of Giovanni Aguto in the assessment both by contemporaries and in the subsequent historical tradition. Giovanni Aguto combined the cruelty and greed of a mercenary captain, on the one hand, and chivalrous gestures and attitudes, on the other.