Alice Chaucer, Countess of Salisbury and Duchess of Suffolk, is one of the very rare people, and the only woman, not born to nobility who became an important political player in the upheaval of fifteenth-century England. Widowed, remarkably enough, at the age of 11, that ‘marriage’ nevertheless set her on the road to power and riches. Her second husband, the Earl of Salisbury, would die at the Siege of Orléans during the Hundred Years War. Her third husband, William de la Pole, was Henry VI’s Chief Minister ‒ and paid for that allegiance with his life, murdered and thrown into the English Channel. Alice survived all this and more – including a state trial in 1451 – and at the same time was a patron of the arts, commissioning artworks depicting empowered historical female characters, notably St Anne, mother of the Virgin Mary. Alice possessed a large library. As late as 1472, Alice became custodian of Margaret of Anjou, her former friend and patron. She ruthlessly protected the inheritance of her son John de la Pole, and three of his four sons would pursue the Yorkist claim to the throne against Henry VII: they would all die in the attempt. Is it going too far to call Alice Chaucer a proto-feminist? If one considers her choices of subject matter as an art patron, it might not be.