Wentworth, with the support of two leading merchants of Bishop’s Lynn, Henry Betley and John Wace, entered the freedom of the town on 13 June 1382, on payment of a £2 admission fee.
Within a few years of his admission as a burgess, Wentworth had become a jurat, and he later had spells in office as chamberlain, constable and coroner of the borough. He was chosen as an elector of the town officers every August between 1390 and 1393, and of the parliamentary burgesses in 1392 and 1406, on the latter occasion providing mainprise for the attendance in the Commons of one of his fellow potentiores, Thomas Brigge. On 28 Sept. 1397, the day before the end of the Westminster session of Wentworth’s second Parliament and when he was again discharging the duties of coroner, the sheriff of Norfolk was instructed to make arrangements to find a replacement on the ground that he was insufficiently qualified for the post.
In the meantime, in August 1411, Wentworth had joined with eight others, including Edmund Oldhall, the prominent duchy of Lancaster official, in undertaking to pay a group headed by Sir John Ingoldisthorpe, the large sum of £900 in instalments spread over a number of years. The purpose of this transaction is unclear, although his subsequent enfeoffment of the manor of Walsham, Suffolk, by Elizabeth, widow of Sir William Elmham, may have been connected with it, for Oldhall and Ingoldisthorpe were both included among his co-feoffees.
