Ramsey probably came of a burgess family of Great Yarmouth, though nothing certain is known of his ancestry. He was admitted to the freedom of the borough before 1384, and came to hold a number of properties there, including two ‘fish-houses’ and a mansion, to which last he built an extension in 1400. Late in life he occupied a small estate at West Somerton, a few miles to the north of the town, which may have been acquired by purchase. His properties in Suffolk, notably the manors of Kenton and ‘Kenton’s’ in Kettleburgh, came to him through marriage.
Ramsey’s early career passed in the service of Sir Simon Burley, an important figure in the household of the young Richard II, and it may well have been to Burley’s influence that he owed his appointment to the office of the chief serjeanty of Meath eight months after Richard’s accession. He was given specific authority to execute the office by deputy should he choose to do so, and accordingly in October 1379 he nominated the archdeacon of Dublin to act as his attorney in Ireland for one year. Meanwhile, in the autumn of 1378, described as Burley’s esquire, he had received money at the Exchequer on his master’s behalf, a function he was to perform several more times before Burley’s fall; furthermore, by August 1380 he was officiating as Sir Simon’s deputy constable at Windsor castle. From 1386 Ramsey figured among Burley’s feoffees of the manor of Castle Frome (Herefordshire), holding it to Sir Simon’s use for what remained of the latter’s life. He clearly benefited from his master’s position at Court: in January 1383 he had been described as a ‘King’s esquire’ when making offerings on Richard II’s behalf in Westminster abbey,
In the 1380s Ramsey began to take an interest in East Anglian affairs. In May 1384 he received a royal grant of the office of controller of customs at Great Yarmouth for term of his life, only voluntarily to surrender it a few months later so that it might be given to another. In February 1385 he stood surety for Robert Waleys, the collector of customs at Ipswich, who was prosecuting a suit in the Crown’s interest. Then, in August that year, he was elected as one of the four bailiffs of Great Yarmouth who were to take up office at Michaelmas, and in the course of this bailiffship he was elected to represent the borough in the House of Commons for the first time. He went on to serve as bailiff five more terms, and to sit for this constituency in seven more Parliaments. Ramsey was commissioned in August 1386 to examine the fortifications of Great Yarmouth in preparation for an anticipated French invasion from Flanders; and at the end of the session of the Parliament of that year he secured appointment as customer in the port. He was still in Sir Simon Burley’s service and enjoying some influence at Court: indeed, in December 1386 a royal pardon for homicide was issued at his personal supplication. In October 1387 he and Hugh Scogan, another of Burley’s esquires, were involved in a dispute with Hugh Fastolf, formerly Sir Simon’s lieutenant at Dover castle and as warden of the Cinque Ports, but the cause of their quarrel is not revealed.
Nevertheless, in the last years of the reign, and probably at the time of the Parliament of 1397-8, Ramsey formed an attachment to Henry of Bolingbroke, heir to the duchy of Lancaster, who before going into exile in the autumn of 1398 retained him with an annual fee of £10. Consequently, when Henry returned to England Ramsey was ready to support him. He was probably with his lord’s forces at Bristol in August 1399, for on 8 Sept. by Henry’s authority he removed from the custody of the mayor and sheriffs there all the goods which had belonged to Richard II and his immediate supporters. Then, on 28 Nov., already made a ‘King’s esquire’ to Henry, who had meantime seized the throne, he received a grant of a substantial annuity of £40 from the fee farm of Great Yarmouth. In the following February he was given the short ‘hanselyn’ with silver-gilt ‘spanges’, which had belonged to the traitor Thomas, Lord Despenser; and in March he was awarded the reversion, expectant on the death of Sir George Felbrigg, of St. Olave’s ferry over the river Waveney between the counties of Norfolk and Suffolk, which produced revenues of £20 a year. Furthermore, that September he and his wife received a grant of two tuns of Gascon wine yearly for life from the royal prise of wines in Great Yarmouth. Felbrigg died before November 1401 when all these gifts were confirmed. Ramsey was thus now assured of royal annuities worth £70, and as a member of the Household he was also allocated liveries of cloth for summer and winter use.
Ramsey never again sat in Parliament for Great Yarmouth, nor accepted election as a bailiff, but in 1401 he was asked to act as a mediator in the burgesses’ longstanding dispute with the men of Lowestoft concerning their respective rights in the herring trade at Kirkley Road. From April to July 1402 he was attached to the retinue of Henry IV’s elder daughter, Blanche, on her journey to Germany for her marriage to Louis, duke of Bavaria. Shortly after his return home he was elected to represent Suffolk in the Parliament which met on 30 Sept., during the session obtaining a patent which bestowed St. Olave’s ferry after his death on his sons, Ralph and William, for term of their lives.
Ramsey’s annuities were confirmed by Henry V. In the course of the next few years he obtained two more pardons of outlawry for failing to appear in the lawcourts to answer charges of debt brought by Robert Luton, a London draper, and Mark le Faire, the prominent merchant of Winchester. He was now gradually retiring from participation in local government, and it was his son and namesake who entered a contract in April 1415 to serve Henry V in France, and who subsequently fought at Agincourt.
Ramsey died on 22 Jan. 1419, leaving as his heirs his sons Ralph, who died in 1421, and William, who was retained by Sir Thomas Erpingham with an annuity of 20 marks.