Although Sheringham was long an important man in Leicester, little can be discovered about him. He came from a family established in the town since at least 1378, when a John Sheringham was named on the merchant guild roll. Another John, not improbably our MP’s uncle, was a canon of the New College in the 1440s.
During the first part of Sheringham’s career he appears to have made his living as a fishmonger. He was described as such when, in 1455, he sued another fishmonger of Leicester for a debt of as much as £15. Later, however, he was styled ‘draper’. In 1477 it was as a draper that he was involved in the resettlement of the property of John Frisley, a former mayor.
Sheringham’s high standing in Leicester at the end of his career is attested by his election on four successive occasions as one of the three stewards of the fair. He last appears in an active role during the fourth of these annual terms: in June 1481 he witnessed a deed on behalf of a local grocer. He was dead by February 1485, when described as a deceased feoffee of John Frisley. His son, William, took over his lease of the duchy croft in the Horsefair, but he never achieved Robert’s prominence in the town’s affairs. He did not serve as mayor and is not recorded as having been returned to Parliament, although he did hold the lesser offices of fish tester and chamberlain.
