A Welshman of obscure background, Montgomery won fame and fortune as a soldier in France. Knighted in 1418 and a banneret by the late 1420s, he helped to capture Joan of Arc and later in life he was twice considered for admission to the Order of the Garter. He first comes into view in 1414, when he successfully petitioned Parliament for an exemption from an Act of 1401 forbidding Welshmen from purchasing land in England. In the petition he referred to himself as ‘esquier bailla a Roy’, indicating that he was already a member of Henry V’s household when he submitted it.
It was as a member of the retinue of Sir John Cornwall that Montgomery returned to France on the King’s expedition of 1417,
Montgomery succeeded the late Hugh Stafford, Lord Bourgchier, as captain of Domfront in the autumn of 1420. In the summer of the following year the King led an army against Chartres, sending orders in August 1421 to Sir John and other captains to send troops from their garrisons to his support.
For several weeks during 1423, Montgomery was both captain of Domfront and deputy commander at Argentan to the east. He exercised the latter position on behalf of the Regent of France, John, duke of Bedford, with whom he fought at Verneuil in August 1424. In the wake of this Anglo-Burgundian victory, which gave the English the opportunity to consolidate their position north of the Loire, Montgomery campaigned with Thomas, Lord Scales and Sir John Fastolf in Maine and Anjou.
When Bedford returned to England to raise more troops at the end of 1425, he was accompanied by Montgomery. In spite of his lengthy absences from home and a consequent lack of involvement in domestic affairs, Sir John was able to gain election – perhaps with Bedford’s support – as one of the knights of the shire for Hertfordshire to the Parliament of 1426. The Parliament met in the midst of a serious dispute between the duke of Gloucester and the chancellor, Henry Beaufort, bishop of Winchester. While it is impossible to confirm that Montgomery was associated with either side when he entered the Commons, it is worth noting his receipt of robes from Gloucester in 1419, and that it was as representatives of the duke that he and others had received the surrender of Ivry in the same year.
Elizabeth’s interests at Cheshunt included the patronage of the local parish church but she, Montgomery and her Norbury sons agreed to surrender this advowson to the duke of Bedford, Cheshunt’s feudal overlord, in 1433, an arrangement ratified by the Parliament of that year.
Within a month of the dissolution of the Parliament of 1426, Montgomery and four mainpernors, headed by John Tyrell* and Lewis John, were bound over in Chancery, he in £40 and they in 40 marks each, that he would do no harm to the Hertfordshire landowner Robert Louthe†. Dated 27 June 1426, these securities might indicate that the quarrel, of unknown origin but possibly connected with Elizabeth Montgomery’s interests in Hertfordshire, had already seen some violence. Some two years later, Louthe entered recognizances for 200 marks to
Almost immediately after providing the security of June 1426, Montgomery was preparing to accompany the duke of Bedford to France. In July that year he obtained letters of protection and attorney prior to crossing the Channel,
It would appear that the MP paid a brief visit to England in late 1430 or early 1431, since in April 1431 he obtained letters of attorney and protection prior to embarking for France.
As the English position in France steadily worsened, so the MP’s career as a soldier began to wind down, and in September 1441 he relinquished his captaincy at Arques, his only known military command at that date. A year later Montgomery was appointed to an embassy headed by Richard, duke of York, the King’s lieutenant-general in Normandy and France. The envoys were mandated to treat for peace with the French although it is uncertain whether any talks took place. Decided upon by Henry VI’s Council in the autumn of 1442, the mission was a sign of the times, exemplifying as it did the increasing weakness of the hard-pressed English, in the face of insufficient resources and the enemy’s recent military successes.
Fiascos like Somerset’s expedition contributed to a growing disenchantment with the government on the part of York and other veterans. Montgomery, whose connexion with the duke dated back to at least the late 1430s, when York granted him a couple of stewardships on his English estates, must have shared this discontent but he chose to maintain links with the Court. In January 1445 Henry VI granted a tun of Gascon wine from the port of London every Christmas to Montgomery (described as a ‘King’s knight’ in the letters patent) and his wife Elizabeth in survivorship, and at the end of the same year the MP and his younger son, Thomas, received a grant of the royal lordship of Worplesdon in Surrey on the same terms.
The English position in France was close to collapse when Montgomery died on 27 June 1449, by which date he had probably lost most, if not all, of his French estates. The inquisitions post mortem for his English lands were held in the following autumn.
Within a year of Montgomery’s death, Elizabeth was obliged to defend a lawsuit arising from dealings between him and two merchants from Lucca, by then also both dead. The plaintiff, Francesco Micheli, suing as the executor of one of these merchants, Battista de Arnolfini, sought a debt of over £16 from her in her capacity as an executor of her late husband. According to Micheli, the debt arose from bonds that he entered into with the Italians at London in 1445, perhaps in connexion with a purchase of goods.
