The house of Skipwith was an ancient and influential one, deriving its name from the Yorkshire village which was its home for centuries. Over the years, successive generations of the family extended their territorial influence, first by obtaining the manor of Menethorpe in the same county, and then by building up impressive holdings to the south in Lincolnshire. The manors of Ormsby, Laceby, Bigby and Thorpe, together with substantial appurtenances were systematically acquired through a policy of advantageous marriages. Sir William Skipwith, the royal judge, was in fact the fifth of his line to marry a Lincolnshire heiress. His wife, Alice Hiltoft, not only brought him the manors of North and South Hiltoft and Ingoldmells, but also the property which her mother, Alice le Muer, had inherited in Calthorp, Covenham and Uphall, together with extensive farmland in the surrounding countryside. These estates alone were worth over £200 p.a. in 1366; and Sir William thus became one of the richest landowners in the area. He was, moreover, able to consolidate his possessions through purchase, using the profits of his flourishing legal practice to buy land in and around Ormsby. So successful was he as a lawyer, that by 1362 he was serving as both a j.c.p. and a baron of the Exchequer, although three years later he was dismissed for alleged extortion and malpractice. After a period of disgrace, Skipwith again returned to favour, recovering his position on the English bench after a period as c.j.KB in Ireland. By pleading illness, he shrewdly managed to avoid attending upon Richard II at Nottingham in August 1387, and was consequently spared the fate of his colleagues, whose pronouncements on the royal prerogative at that time led to their collective impeachment before the Merciless Parliament of 1388. Indeed, he and his two eldest sons, William and John, the subject of this biography, were prominent among the Lincolnshire gentry who took oaths in March 1388 in support of the Lords Appellant.
Sir William had at least five sons and two daughters. Alice married Robert, 4th Lord Willoughby of Eresby, while her younger sister became the wife of Sir Henry Vavasour of Cockerington, a leading member of the Yorkshire gentry. The judge was no less anxious to make adequate provision for his younger sons, and a marriage was arranged between John Skipwith and Alice, the daughter of Sir Frederick Tilney, one of the richest men then living in Boston. The Tilneys exercised considerable influence in Lincolnshire, and for many years John maintained a close relationship with Sir Frederick’s younger brother, Sir Philip. His connexion with the family probably accounts for his appointment in 1407 as controller of customs and subsidies in Boston—a post which his father-in-law had occupied in the previous century. He appears, moreover, to have benefited from an unusually generous settlement of property, for, although part of the Skipwith estates were entailed upon his elder brother and an income of 40 marks p.a. had been settled upon his mother from the manor of Ormsby, some land was given to him during the lifetime of his father and more came into his hands immediately on the latter’s death. As early as 1370 and again in 1372, Justice Skipwith made over to him a reversionary interest in the manors of Menethorpe and Skipwith should his brother’s issue die out, and he subsequently acquired a similar title to holdings in and around Bigby. A substantial proportion of the judge’s Lincolnshire property was meanwhile granted to him outright: in the spring of 1387, for example, he obtained a release of holdings in Cavenham and Little Grimsby, and from this date onwards he also presented to Asterby church. The manors of Ormsby and Ingoldmells together with land in Laceby were probably left to him by the judge, who died shortly before 1398. It was then, in his capacity as lord of the manor, that he chose a successor to his recently deceased brother, Stephen, the former rector of Ingoldmells. Certainly by October 1398 he and his wife were living at Calthorpe, where they were permitted by licence of the bishop of Lincoln to celebrate mass at a private chapel. In May 1403 he conveyed a moiety of the manor of Laceby to trustees, among whom were his brother-in-law, Sir Henry Vavasour, and his two distinguished neighbours, Sir John Copledyke and Sir Thomas Hawley. The latter also acted as feoffees when, four years later, he made a settlement of the manor of Ormsby, although on this occasion they were somewhat overshadowed by Thomas Langley, bishop of Durham, and William, Lord Roos of Helmsley. Skipwith had, in the meantime, likewise secured his title to an estate in Little Carlton which had belonged to his grandmother. These various transactions may well have been connected with plans for a pilgrimage which Skipwith intended to make at the very beginning of the 15th century. At this time he and one Alice Wytkall entered an agreement with agents of the Florentine banking house of Albertini, whereby a sum of 600 ducats (for which they paid £102) was to be made available for them at Venice. Clearly, if he had such a venture in mind, his first concern would have been to make a proper settlement of his estates.
Not only did John Skipwith escape the financial problems which usually befell a younger son; he was also an ambitious and able man who soon overshadowed his elder brother and came to occupy a dominant position in Lincolnshire society. From 1384 onwards, when he and William became trustees of the manor of Manby for Sir John Roos, he was active as a feoffee-to-uses, most notably in 1391 for his wife’s uncle, Sir Philip Tilney. As we have seen, the two men grew very close: in the previous year Skipwith had stood surety at the Exchequer for Tilney when he assumed the tenancy of the young John Hawley’s manor of Mablethorpe; and Sir Philip subsequently chose him to be one of his executors. Shortly after his friend’s death, in 1394, Skipwith offered securities on behalf of his mother, Margery Tilney, who succeeded him as farmer of the Hawley estates in Lincolnshire and Yorkshire; and four years later he himself obtained a lease of some of this property from the Crown, agreeing to pay a farm of £20 p.a. until the heir came of age.
Somewhat surprisingly, in view of his social and financial position, which effectively placed him above the law, Skipwith did not enter Parliament until 1406, when he and Copledyke sat together for Lincolnshire. The session had just started when Philip Repingdon, bishop of Lincoln, renewed the permit which enabled Skipwith to hear mass in his own home; and a few weeks later he and Copledyke joined with his kinsman, Frederick Tilney (the younger), in offering securities in Chancery for (Sir) John Rochford. Skipwith also struck up a friendship with John Pouger, for whom he stood as a guarantor at about this time. In November 1409 the two men obtained the wardship and marriage of Sir Robert Elkyngton’s son and heir from the King at a cost of £40 payable over a period of seven months. The young man died while still a minor, and his next heir, Ada Elkyngton, engaged Skipwith’s services as her trustee. The MP meanwhile became involved in the endowment of a chantry chapel at Loxton in east Yorkshire, but it seems likely that he was once again acting as a feoffee rather than on his own account.
John Skipwith died in 1415, and was buried at the parish church of Covenham. Sir Thomas, the elder of his two surviving sons, was by then married to Margaret, a daughter of William, 5th Lord Willoughby of Eresby and niece of Sir Thomas Willoughby (to whom the Skipwiths were already related), and promptly succeeded to the family estates. On 2 Sept. 1415, he indented with his mother and the other executors of his father’s will to pay them £126 3s.4d. in three instalments for certain goods and chattels at Ormsby and elsewhere, offering securities of £140 as an earnest of his good intentions. His death, just two years later while his only son was still a baby, left his brother, Patrick, in a particularly influential position; and it was not long before he and his widowed mother were embroiled in a protracted dispute over the right to present to the church of Ingoldmells. Alice (who never managed to collect more than a small part of the £126) lived on until 1436, if not later, retaining dower properties worth £53 a year, while Patrick followed his father’s example, and represented Lincolnshire in Parliament.