By far the most influential figure to represent Carlisle during our period, Robert pursued a busy administrative career not only in the city itself (where he served no less than ten terms as mayor), but also in the county of Cumberland. His appointments as a royal commissioner, customs officer and j.p. were, however, made some time after he last sat in Parliament, and little is known about him during the early years of his career when he was prepared to make the arduous journey to Westminster. In August 1387, by which time he had already attended three Parliaments, Robert was named as a juror at an inquiry held in Carlisle into proposals for the endowment of the cathedral. He served on another jury in 1394, this time to examine a petition by the earl of Northumberland and his wife, Maud, Baroness Lucy, for permission to set up a chapel in Cockermouth castle. Interestingly enough, he also sat on a royal commission of inquiry into the baroness’s claims to the lordship of Cockermouth during this period, which saw his increasing involvement in administrative affairs. The royal pardon accorded to Robert in June 1398 was probably a formality, although he was no doubt anxious to obtain protection in his capacity as a collector of customs in Cumberland. Moreover, from this date onwards, he was involved in a long and costly lawsuit with the prior of Carlisle, who arraigned him on an assize of novel disseisin in August 1398, and continued with his suit for another eight years at least. He was accused of retaining rents worth 20s. p.a. in Carlisle, and after protracted delays and evasions he was ordered, in 1404, to pay arrears of £10 to the prior. John More I and William Stapleton offered substantial sureties on his behalf, but he apparently failed to appear in court, as the same verdict was repeated two years later. By then Robert was himself a member of the county bench, so the affair clearly did him little harm.
The years 1399 to 1425 were undoubtedly the busiest of Robert’s life, since besides his official commitments as mayor he was frequently in demand as a witness to conveyances of property in and around Carlisle. He himself owned at least one tenement in the city (in Abbey Street), and was probably a landowner on quite an impressive scale. His circle of friends reflected his position, including as it did Richard Skelton, sometime sheriff of Cumberland, for whom he offered sureties at the Exchequer, in 1420, when he became farmer of certain crown property in the north-west. But by far the most important of his connexions appears to have been Bishop Whelpdale of Carlisle, who made him bailiff of his liberty of Dalston in, or before, 1421.