eldest son of Richard, earl of Cornwall, afterwards king of the Romans, by his first wife, Isabella, daughter of William Marshall, third earl of Pembroke, and widow of Gilbert of Clare, seventh earl of Gloucester [q. v.] He was born on 1 Nov. 1235 (Ann. Tewk. in Ann. Mon. i. 98), and was baptised at his father's favourite seat at Hailes, near Winchcomb in Gloucestershire, by Ralph of Maidstone, bishop of Hereford. In 1240 his mother died, and when his father in the same year went on crusade young Henry was left to the care of his uncle, Henry III (Matt. Paris, iv. 44). In 1247 he accompanied his father on his journey to France, which included an interview with St. Louis and a pilgrimage to Pontigny (ib. iv. 645–6). In 1250 he also went with his father and stepmother, Sanchia, in their mysterious and magnificent progress throughout France, and visited Innocent IV at Lyons (ib. v. 97). He also accompanied his father on the latter's visit to Germany to receive the German crown. The party embarked from Yarmouth on 27 April 1257, and landed at Dordrecht on 1 May (Liber de Ant. Leg. p. 26). On Ascension day (17 May) Henry witnessed his father's coronation at Aachen, and next day was solemnly knighted by his father, and a banquet given in his honour of such splendour as to rival the coronation feast (Matt. Paris, v. 641, vi. 366). His German advisers pointed out the impolicy of his surrounding himself with so many Englishmen, and King Richard sent Henry home about Michaelmas along with the majority of his English followers (ib. v. 653; Ann. Dunst. p. 203).
Henry's political career begins with his return to England, where his father had now granted him Knaresborough and some other possessions (John of Wallingford in Mon. Germ. Scriptt. xxviii. 511). At the parliament of Oxford in June 1258 he was one of the twelve (or rather eleven) elected on the king's side to draw up with twelve baronial representatives the provisional constitution (Ann. Burton. p. 447). Yet after the king and his son Edward had sworn to the provisions of Oxford which they drew up, Henry joined the Lusignans in an obstinate opposition to them. He did not, however, accompany the king's half-brothers on their secession to Winchester, but contented himself with refusing to take the oath to the provisions until he had got the permission of his father, on whom he was entirely dependent (Matt. Paris, v. 697). Forty days were given him to consult King Richard (Ann. Burton. p. 444). He must have finally given way, and soon began to incline to the popular party.
On St. Edward's day 1260 Henry acted as proxy for Leicester as seneschal at the royal feast at Westminster (Fœdera, i. 402). In 1262 he started again with his father for Germany, but soon came back accompanied by his nephew Gilbert, the new earl of Gloucester (Cont. Gervase, ii. 215, 216). He now became a regular partisan of Montfort's (Bémont, Simon de Montfort, p. 199), and was looked upon by Simon as a youth of unusual promise. In October he was in England, and the justiciar, Philip Basset [q. v.], was directed to work with him in defeating the designs of Montfort; but, perhaps by way of precaution, Henry was himself summoned to attend the king at Paris in November, and a gift of a hundred marks for his expenses was offered if he came (Fœdera, i. 422). On 10 March 1263 he was back in England along with Earl Warenne and Henry de Montfort (Cont. Gervase, ii. 219). In April he was at a council of barons at London (Wykes, p. 133; Ann. Dunst. says Oxford, but cf. Bémont, p. 199), and then joined in spoiling the estates of Peter of Aigueblanche, the foreign bishop of Hereford. In June he pursued John Mansel [q. v.] on his flight to France, and was arrested at Boulogne and imprisoned by Ingelram de Fiennes at the suggestion of Mansel (Cont. Gervase, ii. 222). This angered the barons greatly, and Simon de Montfort insisted on his release as a condition of the peace then being negotiated. Henry III agreed to this, and Henry of Almaine, released through the good offices of St. Louis, returned to England (Ann. Dunst. p. 223). On 10 July King Richard thanked his brother for his exertions on Henry's behalf (Fœdera, i. 427). On 23 Aug. Henry was again in England, and sent with Simon and Walter de Cantelupe [q. v.], bishop of Winchester, to treat with Llewelyn of Wales (ib. i. 430). In September he was again sent to France (Cont. Gervase, ii. 224). In October he was present at the great meeting of the partisans of both sides at Boulogne (Chron. Dover, MS. Cotton, Julius D. V., in Gervase, ii. 225).
Henry now began to waver. He told his uncle Simon that he could no longer fight on his side against his father and uncle the king, but said that he had resolved never to take up arms against him. Leicester answered that he feared his inconstancy more than his arms (Rishanger, Chronicle, pp. 12–13, Rolls Ser.; cf. Rishanger, De Bellis, p. 17, Camden Soc.) Yet after his return from Boulogne Henry actively joined Edward, under whose strong influence he remained for the rest of the war against Leicester. He received from Edward a grant of the manor of Tickhill. He was with Edward when he attempted in vain