This article discusses the transformation of the Trissino villa in Cricoli and the pivotal encounter between an impoverished stonemason named Andrea di Pietro della Gondola, and Gian Giorgio Trissino – poet, diplomat and playwright. It was Trissino who initiated the transformation of the villa in Cricoli in the late-Renaissance classicising style, inspired by the architecture of ancient Rome. Recognising the young stonemason’s talent, the scholar from Vicenza provided financial support for his further education, granted him access to his private library, and accompanied the future architect and theorist on three his formative journeys to Rome. The encounter between Andrea di Pietro della Gondola and Gian Giorgio Trissino proved a decisive turning point in the future architect’s life and career. Gian Giorgio Trissino gave the emerging architect the humanist pseudonym ‘Palladio’, and their meeting proved the pivotal first step in the decades-long career that Andrea Palladio’s would pursue in Vicenza. The article also explores the sources of inspiration behind the remodelling of Villa Trissino in Cricoli and considers whether Andrea Palladio should be credited as its author or co-author.