Although Aylesby remains an obscure figure, it appears that he began his career in Henry V’s reign, trading as an ironmonger in London, and also dealing in wine,
At some point in the late 1420s or early 1430s Aylesby fell out with one of the most prominent merchants of Salisbury, the fiercely litigious Thomas Freeman*. He was forced to petition the chancellor to try to obtain repayment of sums of money he had guaranteed for the ransoms of certain Englishmen taken prisoner across the Channel. After the four men (who came from Newcastle, Chichester, Guildford and Sandwich) had been seized by Bretons and taken to St. Malo, Aylesby’s factor Ralph Somer of Salisbury had raised a total of £22 for their ransoms, and the prisoners were bound to the factor as security, to content Aylesby. But Somer, for the ‘graunde affiance et troust’ which he had in Freeman, handed the obligations over to him to levy the sums due from the goods of the prisoners. Aylesby had no remedy in common law to enable him to retrieve his money.
A few years later Aylesby moved back to London. As ‘the elder’ and described once more as ‘citizen and ironmonger’, on 1 May 1445 he placed his goods and chattels in the hands of a number of ‘gentlemen’, a draper and a scrivener of London, and two Salisbury men (one of them being Simon Poy*).
