Henry initially sought to recover territory lost to Castile by assisting the revolt of King Alfonso X of Castile's brother Philip in 1270. He eventually declined, preferring to establish an alliance with Castile through the marriage of his son Theobald to Alfonso X's daughter Violant in September 1272. This failed with the death of the young Theobald after he fell from a battlement at the castle of Estella in 1273.
Henry initially sought to recover territory lost to Castile by assisting the revolt of King Alfonso X of Castile's .brother Philip in 1270 He eventually declined, preferring to establish an alliance with Castile through the marriage of his son Theobald to Alfonso X's daughter Violant in September 1272. This failed with the death of the young Theobald after he fell from a battlement at the castle of Estella in 1273.