PLEASINGTON, Sir Henry (1397-1452), of Burley, Rutland.

Published in The History of Parliament: the House of Commons 1386-1421, ed. J.S. Roskell, L. Clark, C. Rawcliffe., 1993
Available from Boydell and Brewer



Family and Education

b. Stamford, Lincs. 25 Mar. 1397, 2nd s. and h. of Sir Robert Pleasington*. m. (1) by Apr. 1414, Agnes, da. of Roger Flore* by his 1st w.; (2) by Mar. 1425, Isabel (1402-71), da. and h. of Aubrey Wittlebury (d.1406) of Wittlebury and Whissendine, Rutland by his w. Margery, 1s. 1s. illegit. Kntd. by Jan. 1420.1

Offices Held

Commr. to raise royal loans, Rutland Apr. 1421, May 1428, Feb. 1436, Nov. 1440, Sept. 1449; assess a grant Apr. 1431.

J.p. Rutland 12 Feb. 1422-d.

Sheriff, Rutland 12 Dec. 1426-7 Nov. 1427, 26 Nov. 1431-5 Nov. 1432, 4 Nov. 1440-1.

Assessor of a tax, Rutland Jan. 1436, Aug. 1450.


Pleasington was just over ten years old when his elder brother, Robert, who was himself still a child, died, leaving him heir to an extensive estate spread over at least seven English counties. Part of this lucrative inheritance was then burdened with dower settlements made upon his mother, Isabel, and Agnes Pleasington, the long-lived second wife of his celebrated grandfather, Sir Robert; but both women died before his coming of age, thus enabling him to gain control of his entire patrimony. Proofs of age were taken at his birthplace, the town of Stamford, in January 1420, and over the next few months Pleasington received custody of the manor of Burley and land in Alsthorpe, Rutland, which produced at least £22 a year, two houses and a garden in Holborn, Middlesex, certain unspecified holdings worth £20 p.a. in Southampton, the manor of Ellal with its appurtenances in Lancashire and a considerable amount of property in Yorkshire, comprising the three manors of Healaugh, Reeth in Swaledale and Ilkley, as well as numerous plots of land and tenements scattered throughout the Craven area of the West Riding. Pleasington also appears to have inherited the manor of Toynton in Lincolnshire, which increased his revenues by a further £20 a year.2 It was almost certainly through his mother, an heiress in her own right, that he claimed the manor of Bilton in Holderness. Although he experienced some legal problems in establishing his title, the manor eventually passed into his hands, and when he died his annual revenues from Yorkshire alone were conservatively estimated at £50.

We do not know how Pleasington obtained the land in the Northamptonshire village of Thorpe which was his by 1428, but it may perhaps have come to him through marriage. His first wife, Agnes, the daughter of Roger Flore, does not seem to have brought him much in the way of property, although, as we shall see, the connexion which he thus established with one of the most prominent employees of the duchy of Lancaster was to prove crucial in the early years of his career. His subsequent marriage to John Wittlebury’s* grand daughter, Isabel, turned out to be far more lucrative in purely financial terms, since she was heiress not only to the manor of Wittlebury itself but also to an impressive estate in and around Empingham in Rutland. No doubt because he was increasingly preoccupied with both public and private affairs in this part of England, Pleasington decided to dispose of some of his outlying properties. In 1428, for example, he sold his various tenements in Southampton to a local man, and at some point over the next seven years he leased out his houses in Holborn, the revenues of which had been initially used to pay the annuity of £5 settled by his father upon Richard Banks, one of the barons of the Exchequer. At the time of his death, in the autumn of 1452, our Member appears to have been living in the City of London, and he made provision in his will for the construction of a tomb bearing his coat of arms in the chapel of St. Mary’s hospital without Bishopsgate.3

Pleasington had barely achieved his majority when he became involved in local politics, almost certainly through the influence of his distinguished father-in-law, Roger Flore, whom he had known from early childhood. Flore’s appointment in 1401 as one of the custodians of the estates and person of his father (who was then suffering from intermittent bouts of insanity) marked the beginning of their long association, which was clearly based in its later years upon mutual feelings of respect and affection. Pleasington first attended the parliamentary elections for Rutland in 1419, when Flore was elected. The latter, in turn, helped to secure his return to the Parliaments of 1420 and 1425, both men being chosen, meanwhile, to sit together as shire knights in 1422. This, the first Parliament of Henry VI’s reign, was the occasion of Flore’s fourth and last tenure of the Speakership, an office in which he possibly received practical support from his young son-in-law. Pleasington was also present in the county court at Oakham when Members were returned to the Commons of 1421 (May), 1423, 1426 and 1429. He first held office as sheriff of Rutland during this period, although by then he had clearly come to rely far less upon Flore and more upon his own resources of wealth and patronage, which were by no means inconsiderable. On making his will in April 1424, Flore selected Pleasington to oversee the work of his executors, enjoined him to take particular care of his younger children and rewarded him with the gift of his ‘next best ambler’. Pleasington’s wife, Agnes, and her elder brother, William, were the only two of Flore’s offspring not to be mentioned in this document, which suggests that she had already been dead for some time when he remarried approximately one year later.4

Meanwhile, in June 1421, Pleasington obtained permission from the Crown to appoint attorneys for the supervision of his affairs while he was serving with the King in France. So little information has survived to illuminate his more personal activities that we are thrown back upon such scraps of evidence as his appearance in January 1429 among the witnesses to one of Sir Thomas Burton’s* property transactions in Rutland, and his association with William, Lord Zouche, and Thomas Langley, bishop of Durham, as a trustee of certain land in Cottesmore which was brought by another of his neighbours a few years later. Understandably, in view of his prominent’ position in local society, Pleasington was one of the residents of Rutland required in May 1434 to swear that they would not assist any persons disturbing the peace. His younger brother, John, who lived at Whissendene (where the manor of Wittlebury lay), also took this oath, and it seems likely that the two men remained fairly close throughout their lives.5

Pleasington died on 10 Sept. 1452, having previously settled most of his Yorkshire estates upon his second wife, Isabel. The rest of his property descended to their only surviving child, William, a youth of about 16, who became the ward of Edmund, duke of Somerset, and died suddenly in the autumn of 1457, just after his coming of age. He was succeeded by his cousin, Isabel, the wife of Sir John Fraunceys of Burley, but she too met an early death. Our Member also left an illegitimate son, named John, to whom he bequeathed an annuity of five marks payable for life from the manor of Toynton. In addition he specified that the manor of Ilkley should be sold to raise money for pious works, although his widow subsequently sued one of his executors when he attempted to implement this bequest, accusing him of both forgery and fraud. She lived on until the beginning of 1471, when her own estates reverted to Robert Wittlebury, one of her kinsmen.6

Ref Volumes: 1386-1421

Author: C.R.


  • 1. C137/58/48; C138/37/29; C139/148/3, 169/34; C140/33/43; VCH Rutland, ii. 115, 160, 246; Reg. Repingdon (Lincoln Rec. Soc. lvii) i. 36-37; Fifty Earliest Eng. Wills (EETS, lxxviii), 55-59; Genealogist, n.s. x. 35. Two curious references in the fine rolls state that Pleasington died shortly before 13 May 1450 (CFR, xviii. 133, 155), but it is clear both from his will and inquisition post mortem that his death occurred on 10 Sept. 1452 (PCC 17 Rous).
  • 2. Feudal Aids, iii. 297, 350; iv. 213; vi. 456; C138/37/29; C139/148/3; CPR, 1408-13, p. 148; CFR, xiii. 159, 204; VCH Yorks. (N. Riding), i. 240; E. Williams, Early Holborn, i. nos. 842, 864; CCR, 1419-22, p. 33.
  • 3. C139/148/3; VCH Rutland, ii. 160, 246; G.H. de S.N.P. Harrison, Yorks. 249; HMC 11th Rep. III, 81-82; Feudal Aids, iv. 49; Williams, i. no. 853; ii. nos. 1063, 1077; PCC 17 Rous.
  • 4. CPR, 1399-1401, p. 473; C219/12/3, 5, 13/2-4, 14/1; J.S. Roskell, Commons of 1422, pp. 83, 211; Fifty Earliest Eng. Wills, 55-59.
  • 5. DKR, xliv. 628; CP25(1)192/9/6; T. Blore, Rutland, 216; CPR, 1429-36, p. 370.
  • 6. PCC 17 Rous; C1/16/647a; C139/148/3, 169/34; C140/33/43; Harrison, 249; Williams, i. no. 853; CFR, xviii. 155; xix. 201; CPR, 1452-61, p. 30. William Pleasington married Margaret, the daughter of Henry, Lord Scrope of Bolton (Genealogist, loc. cit.).