Possibly a native of the Channel Islands, Appleby, after serving as a royal commissioner in Jersey, successfully petitioned for the office of royal receiver and approver of the isles.
Although in June 1384 Appleby was awarded a royal annuity of 20 marks, which was to continue until he had received the sum of £72 4s.5¼d. due to him on his Channel Islands account, he was again in trouble with the Exchequer two years later, this time concerning his office as controller of customs, and an inquiry was authorized into his alleged perpetration of forgeries. Four years after his name had been cleared and the office in question bestowed on him for life, he resigned it. At Michaelmas 1390, when the municipal authorities of Southampton granted him a lease of the local customs for one year, Appleby was described as a merchant, but the only strict evidence of his commercial activities is a Portuguese trader’s claim in Chancery that he owed him 215 marks. He is known, however, to have had business dealings of some sort with a knight of the shire for Hampshire, Henry Popham, esquire. On 22 Nov. 1391, when up at Westminster for his third Parliament, and even while the Commons were in session, Appleby was arrested and imprisoned in the Tower of London; he subsequently appeared before the royal council to answer charges, perhaps connected with his new post as customs’ collector, but once more he escaped conviction. Four years later, and now as a royal serjeant-at-arms, he was authorized to requisition ships in the West Country for the transportation of the earl of Huntingdon and his men to Ireland, but this was his last recorded service for Richard II, and in June 1398 he took out a royal pardon. It may be the case that in 1399 he actively assisted Bolingbroke’s usurpation of the throne in some way, for two months after Henry’s accession he secured an annuity of £10 for good service.
The most important of Appleby’s Southampton properties, and no doubt his dwelling, was West Hall in French Street, which he had leased from the hospital of St. Julian since 1383 at an annual rent of 26s.8d., and which was used by the royal customers until 1407 to house the wool-beam. But he also held three other buildings, including ‘The Vernacle’, in the same street. In 1392 Sir Nicholas Dabrichecourt granted Appleby a plot and rents of £4 p.a. during the lifetime of the widow of Roger Mascall, and from 1406 he leased the ‘Redehall’ along with gardens and a stable opposite Bugle Hall. Although in the following year it was alleged that Appleby had been withholding rent due to St. Julian’s for the past 20 years, in 1409 he secured from the hospital an 80-year lease of gardens in Bugle Street.
In 1416, three years after Appleby’s death, his daughter Alice, wife of Robert Bartholomew alias Mayhew, formally gave up her rights to his estate. His widow married John Pole, esquire, and in 1420 certain houses of which Appleby had enfeoffed Thomas Beaufort, duke of Exeter, were released to the couple and later sold. In 1429 West Hall was purchased by the town.