One of the most overlooked families of the early modern period, the Courtenays played a critical role, and their story of love and loss, loyalty and betrayal, survival and ruin is played out at the courts of four Tudor monarchs. Katharine, Countess of Devon, was Edward IV's daughter. Her first proposed marriage would have made her Queen of Spain, but she was declared a bastard on the accession of her uncle Richard III. Legitimated under Henry VII, she eventually married Sir William Courtenay, heir to the earldom of Devon. Her closeness to her sister, Queen Elizabeth of York, did not prevent the sudden arrest of her husband in 1502. Whilst earning the regard of her royal brother-in-law, Henry VII, she walked a knife edge until the accession of her nephew, Henry VIII. As a widow, he granted her the lands of the earldom of Devon for life, making her one of the wealthiest female magnates in England. Her death in 1527 spared her the tragedies which befell her family in the 1530s. Her son Henry, Marquis of Exeter, was first cousin to Henry VIII, with whom he enjoyed a close relationship until the king’s decision to repudiate his queen changed everything. Henry’s marriage to Gertrude Blount, one of the most neglected women of the Tudor period, was one of affection and respect. During the 1530s, she was at the centre of a group opposed to Henry VIII’s repudiation of Catherine of Aragon, passing on information provided by her husband and a small circle of trusted friends to the imperial ambassador, Chapuys. When her husband was arrested in 1538, he, along with others, was executed; only she survived. Imprisoned in the Tower with her twelve-year-old son, Edward, she was later released while Edward remained incarcerated until the accession of Mary I. Upon his release, many believed he would marry the queen, but instead, he died in exile from suspected poisoning after surviving several assassination attempts by imperial agents. This study of the Courtenay family follows their lives and fortunes from 1479-1558.