Thomas Chalers was aged four when his father died during the Merciless Parliament of February 1388. The Lords Appellant permitted his mother, Margery, and Sir William Castelacre to have custody of the estates of his inheritance, but his marriage was granted for £20 to an esquire of Thomas, duke of Gloucester, named John Corbet, who promptly sold it to the former Speaker, Sir Richard Waldegrave, and others including John Rokell. It was Rokell who had personal charge of the boy when in October an agreement was reached whereby his mother and her new husband, Sir John Heveningham, were given the Hertfordshire manor of Wyddial as well as annual rents of £4 from property at Reed in lieu of her dower portion. These were probably the properties which, still in Heveningham’s possession in 1412, then provided him with an annual income estimated at £20; and Chalers was not recorded as holding this part of his patrimony until after his stepfather’s death in 1425.
In 1415 Chalers enlisted for service on the expedition to France as a man-at-arms in the retinue of Humphrey, duke of Gloucester; but he fell ill at the siege of Harfleur and was probably among those sent home in October, before Gloucester’s depleted force marched on to Agincourt. Although his name was on the list of 12 men returned from Cambridgeshire to the King’s Council in January 1420 as being best qualified for military service in the defence of the realm, he was never put on royal commissions of array, and it was not until the spring of 1421 that he again embarked for France, once more under Gloucester’s command. Whether through personal choice or simply as a result of his failure to distinguish himself in the field, he was never knighted. Chalers’s participation in local administration was similarly hardly worthy of remark, save for his single term as sheriff, during which he held elections to the Parliament of 1427.
Chalers died on 7 Feb. 1443 and was succeeded by his son John, then aged 29. Described shortly afterwards as a ‘King’s knight’, Sir John was to represent Berkshire in the Parliament of 1447.
