A sense of family obligations or unity is not always associated with Henry II and his sons. Henry the Young King, Richard, and Geoffrey of Brittany all rebelled against their father, more than once, in the 1170s and 1180s. John, the youngest son, joined Richard I's alliance with Philip II of France when it became clear that the old king was dying in 1189. The betrayal allegedly caused Henry II to despair of life on his deathbed at Chinon. If this was a recognition of political reality, John proved a greater threat to his family during Richard I's early years as monarch. The crusader king provided his younger brother with a lavish landed endowment, but John was at once a potential heir and a possible threat. The Lionheart showed his awareness that his brother might seek the throne for himself by retaining key castles in the hands of loyal servants, excluding John from the regency council, and initially making him swear an oath to stay out of England for a period of three years (his anticipated absence on crusade). The latter demand was rescinded, but John failed to live up to his elder brother's trust. Eleanor of Aquitaine, said to have intervened to secure John's release from his oath, was forced to act to prevent his alliance with Philip II when the French king returned from the crusade. John then attempted to seize the throne during the period of his brother's captivity.

Critics of the Angevins were well aware of this apparent lack of family unity and its destabilising consequences. Bishop Hugh of Lincoln was credited with the ability to prophesy the dynasty's future. He blamed what he regarded as the unlawful marriage of Henry II to Eleanor of Aquitaine, following the annulment of her union with Louis VII of France (1152). On his deathbed in 1200, the bishop is said to have declared: ‘the words of the Bible must inevitably be fulfilled in the case of the descendants of King Henry, “Bastard shoots will not have deep roots” and “the offspring of an adulterous union shall be destroyed”’.