This article concerns the letters of Mary Tudor Brandon, known as Mary the French queen, who defied her brother Henry VIII by secretly marrying her second husband, the Duke of Suffolk. Mary’s use of the epistolary genre to persuade Henry to accede to the match was born not merely out of necessity, but out of her awareness that letters were a powerful political tool that women could employ to further their ambitions. Of particular interest is a letter that survives only in draft with marginal comments by then Archbishop Wolsey, a letter which demonstrates Mary and Wolsey’s complex maneuverings to negotiate the terms that would result in a pardon for the couple and allow their return to England. Moreover, placing Mary’s letters within a literary context reveals the influence of fictional letters, especially Ovid’s Heroides, which Mary studied in French while preparing for her first marriage, to Louis XII. Crafted with multiple audiences in mind, her letters are an excellent case study of queenship, power, and women’s political and literary activity during the early sixteenth century.