Countess Maud, was born about 1299, and was called ‘of Grosmont,’ possibly from the place of his birth. He is said to have gone while a young man to fight as a crusader in Prussia, Rhodes, Cyprus, and Granada, to have been so renowned a captain that he was known as ‘the father of soldiers,’ and the noblest youths of France and Spain were anxious to learn war under his banner (Capgrave, p. 161). He served with distinction in the Scottish war of 1333, especially at the taking of Dalkeith. In 1334 his father made over to him the towns and castles of Kidwelly and Carwathlan, with other lands in Wales, and on 3 Feb. following he was summoned to parliament as Henry de Lancaster. On 15 April 1336 Edward III, who was his cousin, appointed him to command an army against the Scots (Fœdera, ii. 936); the king went to Scotland in person, and Henry, who was then a knight-banneret, was with him at Perth, and on 12 Dec. was named as a commissioner for the defence of England against the French (ib. p. 953). On 16 March 1337 Edward created him Earl of Derby, one of the titles borne by his father, who was still living, as the heir of Earl Thomas, and assigned him a yearly pension from the customs. In November he was sent, along with Sir Walter Manny, to attack the garrison of the Count of Flanders in Cadsant. There he showed himself a gallant knight, for on landing he advanced so near to the fortifications that he was struck down. Sir Walter Manny saw his danger, and shouting, ‘Lancaster for the Earl of Derby!’ rescued him (Froissart, i. 137, 140). When the king sailed from the Orwell for Antwerp in July 1338, Derby sailed from Great Yarmouth in command of the troops conveyed by the northern fleet, and joined the king's ships in the Channel (Fœdera, ii. 1050). He remained with the king, and in October 1339 commanded, under Edward in person, the third battalion of the army at La Flamengrie or Vironfosse [see under Edward III]. Edward was anxious to be again in England, and in December offered to leave Derby in Flanders as a hostage for his return, for he was deeply in debt. However, the earl accompanied him to England in the following February (ib. pp. 1100, 1115), and on 24 June took part in the sea-fight before Sluys, where he behaved with much gallantry (Froissart, ii. 37). When Edward returned to England on 30 Nov. he left the earl in prison in Flanders as a security for his debts, and took measures to procure his release through the intervention of the Leopardi Company. Derby was detained for some months, and had moreover lent the king his jewels, which were pledged for 2,100l. (Fœdera, pp. 1143, 1159, 1176). On 10 Oct. 1341 he was appointed captain-general of the army against the Scots. The English had by this time lost nearly the whole country, and this expedition failed to check the progress of the reconquest; Stirling had already been lost, and Edinburgh Castle was soon lost also. A truce for six months was made in December. The earl spent Christmas at Roxburgh, and while there challenged Sir William Douglas, the knight of Liddesdale [q. v.], to tilt with him; Douglas was vanquished. He also persuaded Sir Alexander Ramsay of Dalhousie to accept his challenge to joust, twenty a side, and in all his exploits gained glory and honour. On 3 April 1342 he was appointed along with others to arrange a peace or a truce with the Scots. In October Derby accompanied the king on his fruitless expedition to Brittany. In the spring of 1343 he was sent on embassies to Clement VI at Avignon, and to Alfonso XI of Castile. While in Spain he and his fellow-ambassador, the Earl of Salisbury, did good service against the Moors at the siege of Algeciras (Chronicle of Alfonso XI). On his return to England he went northwards in August to negotiate with the Scots (cf. Murimuth, p. 158). At the tournament held by the king at Windsor in February 1344 he acted as steward of England, his father's office, and joined in the oath for the establishment of a ‘round table.’ In March he received full powers to treat with the kings of Castle, Portugal, and Arragon, in conjunction with Richard, earl of Arundel (Fœdera, iii. 8).
On 10 May 1345 Derby was appointed lieutenant and captain of Aquitaine, an office which he held until 1 Feb. 1347, and on 22 Sept. succeeded his father as Earl of Lancaster and of Leicester, and steward of England. He sailed from Southampton for Gascony, probably in the middle of June, in company with Sir Walter Manny, and with a force of five hundred knights and esquires, and two thousand archers. His orders were to defend Guienne, and if he thought well, to attack Périgord and Saintogne. Having landed at Bayonne, and spent about a week there and fifteen days at Bordeaux, he set out towards Bergerac, where a number of lords on the French king's side were assembled under the count of Lille-Jourdain to keep the passage of the Dordogne. Pressing on, Lancaster gained the suburbs of the town after a sharp struggle, and the next day, 24 Aug., took the place by assault. He then captured many towns and fortresses in Upper Gascony, failing, however, to take Périgueux, in spite of a plot to deliver it to him. Auberoche