Fennell, a local man, was first recorded in the records of Sandwich in April 1432 when he was one of a number of merchants to whom Edmund Mechelen entered into a recognizance for £20.
After his return home, on the following 7 Dec. Fennell was elected mayor of Sandwich. His year in office saw him attend four meetings of the Brodhull and his appointment as one of the feoffees of the property recently purchased in Yarmouth for the use of the Ports’ bailiffs there during the annual herring fair. In February 1451 he was appointed, ex officio, to inquire into an act of piracy allegedly committed by local men against Dutch ships in the Camber. According to the series of local annals, his mayoralty was also notable for a composition made between the commonalty of Sandwich and the hospital of St. Thomas, concerning rents and other dues in the town after the hospital had lost the majority of its ancient records.
Lacunae in the local records obscure the details of Fennell’s career in the early 1460s, but it seems certain that he continued to serve as jurat, keeper of the keys and deputy mayor throughout the decade. By December 1467 he was also alderman of the town’s third ward, but it is not clear when he began to serve in this capacity. The infrequency with which he now attended meetings of the Brodhull (only twice between July 1461 and his death),
Little evidence survives of Fennell’s private affairs. In 1442-3 he claimed exemption from the parliamentary subsidy in Eastry hundred,
In his will made on 30 June 1473 Fennell left his property in Sandwich, Woodnesborough and Eastry to be divided between his widow, Elizabeth, and his grandson John Fennell (the son of his son John who had predeceased him), in tail male, with remainder to his daughter Christine. He asked to be buried in his parish church of St. Peter’s, near the image of St. Christopher, and left ten marks for prayers to be sung for the souls of his parents and first two wives. He bequeathed a silver gilt maser to his daughter, and gave 40s. to pay for repairs to the road between Sandwich and Eastry. The residue of his goods and chattels was to be disposed of by his executors (his widow and John Iden, one of his fellow jurats), for the benefit of his soul. Probate was granted on the following 27 July.
