"Richard, was living in 1338 and survived the Black Death in 1348 which took heavy toll of the population of New Romney and also through part of the long war with the French, which caused great economic distress in the town, when it was under constant threat of invasion."

Winchelsea, ten miles away, was sacked by the French in 1359 and 1360 and again in 1380, and Rye was burnt in 1377 when 66 of the inhabitants were massacred and others taken hostage.

In about 137O, Edward III took the Manor and the lands of Bilsington, almost adjoining the Cobbe's Estates, under wardship, when the heir, Geoffrey Steelegate was a minor, and sold the benefits to Geoffrey Chaucer for £140. The purchase carried with it the appointment of Chief Butler to the King, and as such he served the King with wine on official occasions, and received honours, fees, and a knighthood for the service, together with the income derived from the estate.

Richerd Cobbe was followed, first by his son Edward, who must have known Chaucer, and then by his grandsons Edmond and Richard. It appears Richard Cobbe, brother to Edmond, held an official position inthe Corporation of Romney, probably that of Justice of the Peace or Chamberlain." (rsc)

More specifically, he was born during the first quarter of the 14th century. Richard also carried the title of Esquire (by the right of his father), and was living at Cobbs Court in the "11th year of the reign of King Edward III" (1338). The name of his wife is lost, but is known that had at least one son, Edward.