Nothing is known of Bentley’s career before his appointment in 1377 as a clerk of the Exchequer. The next few years appear to have passed without incident until February 1384, when Richard II granted him the fee of 8d. per day for life which had previously been paid to Thomas Eltham, the King’s smith, and which Eltham wished to award to the young man. One month later Bentley and Eltham made a joint loan to the Crown of £100 perhaps in recompense for the letters patent sanctioning the transfer.
Bentley’s resignation probably coincided with his marriage, which proved to be a turning point in his career. At some date not long before June 1389 he married Joan, the widow of the Surrey landowner, John Newdigate, and thus acquired an interest in a fairly substantial estate there and in the neighbouring county of Sussex. He lost little time in securing his title to Newdigate’s property in and around the Surrey village of Leigh; and in July 1390 he entered into recognizances of £100 payable to his wife’s mother-in-law, who still retained some of the deceased’s inheritance. It was thus, thanks to his recent entry into county society, that he was returned to Parliament by the Surrey electors in the following November.
Bentley was often involved in litigation: in February 1391, for instance, he brought a suit for debt against a Hereford man, and although he was then acting as an executor of Thomas Orgrave, several other cases appear to have affected him more personally. During the early years of the 15th century he faced at least four actions for the recovery of debts totalling over £152 (£40 of which was claimed by the Crown), and he was also arraigned with his wife on an assize of novel disseisin concerning the ownership of rents in Cheam. Most of these cases ended with the issue of royal pardons for outlawry incurred by his failure to appear in court, although the dispute over rents, which dragged on for almost seven years, came to an abrupt end in December 1423. Bentley must have been well over 60 by then, and it seems likely that he died at about this time. He had already either sold his wife’s estates in and around Leigh, or else, more probably, settled them upon feoffees. He is last known to have been active in the autumn of 1423, when he surrendered his trusteeship of the Middlesex estates of Elena Hull.
