The Derwentwaters were a family of considerable antiquity, whose principal seat lay at Castlerigg on the shore of Lake Derwentwater, whence they took their name. Over the years they acquired the manor of Tallentire and the vill of Threlkeld, also in Cumberland, and the two manors of Ormside and Bolton, across the county border in Westmorland. Sir Thomas Derwentwater† (d.c.1303) was one of the first men to represent Westmorland in Parliament, and his descendants continued to involve themselves in the business of local government. John, the subject of this biography, is first mentioned in 1361, when his godfather, William Brigholm, died, leaving him a small amount of money, a sword and other weapons. His father, Sir John, alienated certain property at Airey and Ullock in Cumberland on the marriage of his sister, Christine, in the following year, but the rest of the family estates descended to him intact. John succeeded his father in the spring of 1366, and was returned to Parliament for the first time at the end of the decade. By February 1371 he had been knighted, and within a short time he embarked upon a busy administrative career which lasted over 20 years.
During his second term as sheriff of Cumberland, in 1376, Sir John ran into difficulties with a prisoner named William Roucliffe, whom he refused to release on bail from Carlisle castle. As a result, Roucliffe’s friends launched an armed assault on him and his bailiff while they were holding court there, and Sir John petitioned the Good Parliament of 1376 for the setting up of a royal commission of oyer and terminer to punish the miscreants. He was entirely successful, in the short term at least, since the commission appointed in June of that year in response to his appeal included his two most influential feudal overlords, Roger, Lord Clifford, and William, Lord Greystoke, of whom he held, respectively, the manors of Ormside and Threlkeld. Sir John may well have travelled to Westminster to present his case in person. At all events, he was named in the following July among the mainpernors of Sir Hugh (later Lord) Dacre, who had been committed to the Tower on the suspicion of murdering his brother, Ralph, Lord Dacre, so that he could inherit his estates and title. Sir John also seized the opportunity to negotiate a lease of the royal demesne lands at Carlisle, which had only just been farmed out to the lawyer, William Soulby. Clearly reluctant to antagonise so powerful a neighbour, Soulby made no attempt to defend his title, and the transfer was effected smoothly. Two other items of legal business soon came to demand his attention: by 1378, if not well before, he sued a local man for damaging his crops at Bolton; and in the following year he began litigation for the recovery of £10 damages incurred because of the forcible abduction of one of his servants. Since he already had personal matters to deal with in the lawcourts, Sir John was no doubt far readier than many of the local gentry to undertake the long and arduous journey to Westminster; and in 1379 he took a seat in the House of Commons for the second time.
Altogether, Sir John represented Westmorland and Cumberland alternately in four Parliaments. While he was at Westminster for the last of these assemblies (the Merciless Parliament of 1388), a group of armed men attacked his manor-house at Bolton, carried off a large part of the contents, and intimidated his servants. Once again he requested that a royal commission should be set up to investigate the affair, and, just as before, his overlord, Roger, Lord Clifford, was appointed to serve as a commissioner. Their relationship must have been quite close by then, because in June and October of the same year Sir John agreed to stand surety for the payment of a sum of 500 marks by Clifford at the Exchequer.
