Of the five Tudor monarchs, only one was ever born to rule. While much of King Henry VIII’s reign is centered on his reckless marriage choices, it was the foundations laid by Henry and Queen Katherine of Aragon that shaped the future of the crown. Among the suffering of five lost heirs, the royal couple placed all their hopes in the surviving Princess Mary. Her early life weaves a tale of promise, diplomacy, and pageantry never again seen in King Henry’s life, but a deep-rooted desire for a son, a legacy of his own scattered childhood, pushed Henry VIII to smother Mary’s chance to rule. An affair soon produced an unlikely heir in Henry Fitzroy, and while one child was pure royalty, the other illegitimate, the comparison of their childhoods would show a race to throne closer than many wished to admit. King Henry’s cruelty saw his heirs’ fates pivot as wives came and went, and the birth Princess Elizabeth, saw long-term plans upended for short-term desires. With the death of one heir hidden from view, the birth of Prince Edward finally gave the realm an heir born to rule, but King Henry’s personal desires and paranoia left his heirs facing constant uncertainty for another decade until his death. Behind the narrative of Henry VIII’s wives, wars, reformation and ruthlessness, there were children, living lives of education among people who cared for them, surrounded by items in generous locations which symbolized their place in their father’s heart. They faced excitement, struggles, and isolation which would shape their own reigns. From the heights of a surviving princess destined and decreed to influence Europe, to illegitimate children scattered to the winds of fortune, the childhoods of Henry VIII’s heirs is one of ambition, destiny, heartache, and triumph.