Doyly’s origins are obscure, but it seems likely that he was a local man. A Thomas Doyly, esquire, claimed exemption as a Portsman from the parliamentary subsidy in Bewsborough hundred in 1440 and this individual may have been our MP’s father.
Doyly owed his rapid advancement among the governing elite of Dover to his association with the leading Portsman, Ralph Toke, and marriage to his widow. Before 1450 the two men had acted together in land transactions, with Doyly acting as Toke’s feoffee in the purchase of the manor of Goodnestone and other property in Kent. Toke also appointed him executor of his will.
At some point Doyly also appears to have entered the King’s household. This may have occurred in the late 1440s through a connexion with the then warden of the Cinque Ports and Toke’s patron, (Sir) James Fiennes*, Lord Saye and Sele, although he is not listed as receiving fees and robes in the extant Household accounts, or as part of the revised establishment of November 1454. In December that year, however, he sued his fellow Household man, Thomas Tropham, in the marshalsea of the Household for stealing his horses at Southwark.
In September of that year, during the prorogation of the Parliament, Doyly was elected to his first of four consecutive terms as mayor of Dover. During his first mayoral year he continued to serve as a parliamentary baron, receiving £5 8s. for 54 days almost certainly spent at Westminster between February and the beginning of April 1454 (although he attended a meeting of the Brodhull on 9 Apr., nine days before the Parliament’s probable closure).
In September 1457 Doyly was replaced as mayor by Gore. He continued to serve as a jurat and in 1458 he was among the leading Portsmen who victualled Le Michael, a ship appointed to go to sea with the earl of Warwick.
Doyly’s entanglement in the lawsuits concerning the affairs of Ralph Toke began even before his marriage. In Trinity term 1453 he was pursuing Toke’s debtors in the court of common pleas and in Chancery around the same time he sued Thomas Quylter of Goodnestone, a tenant of the manor which he and Toke had purchased together, for refusing to pay rent. On the latter occasion surety for Doyly was provided by Gervase Clifton*, the former lieutenant of Dover castle.
Little other evidence survives of the last years of Doyly’s career. It is clear, however, that the connexions he had made through his membership of the King’s household remained important throughout the 1450s. In 1458 the Brodhull allowed a process of withernam in which he was involved with (Sir) Gervase Clifton,
