Abstract The article considers how Thomas Wyatt—courtier, ambassador and poet maker—became Italianate. It discovers a youthful Wyatt, with other members of Henry VIII’s court, at the company of Giovanni di Lorenzo Cavalcanti and Pierfrancesco di Piero de’ Bardi in London in the 1520s. These Florentine merchant princes were international bankers and traders, and notable cultural brokers between England and Italy. Pierfrancesco was a scholar, a collector and donor of books. Wyatt bought fine Florentine fabrics from the company. They allowed his growing indebtedness, partly through friendship, but also because of their need for the patronage of his father, Sir Henry Wyatt, Treasurer of the Chamber. Wyatt was also part of the gambling fraternity in which Francesco di Bernardo de’ Bardi was a principal player. Leaving Florence for London, the merchants did not remove themselves from the turbulent politics of their city, for their wealth and prominence ensured their continuing involvement, especially once Medici popes ruled Christendom. When Rome was sacked, and Florence established a republic, London’s Florentines were called to their city’s defence. Before he ever travelled to Italy, Thomas Wyatt encountered Italians of wealth and culture living in the grandest style in London, between the worlds of the court and the city. Perhaps with them he began to learn Italian. The story of Wyatt among the Florentines leads to life in London and the court, to the defence of Italy, to the revolutionary politics of Florence, and to Henry VIII’s ‘Great Matter’. Wyatt was precursor, and inspiration, of the Italianate Englishmen and women gathered at the humanist court of Edward VI who were fascinated by Italian culture and won to reform.