Constituency Dates
Rutland [], 1422, 1425
Family and Education
b. Stamford, Lincs. 25 Mar. 1397, 2nd s. and h. of Sir Robert Pleasington† of Ellel, Lancs. and Burley by Isabel (d.1411), prob. da. and h. of Joan, da. and h. of William Bilton of Bilton in Holderness, Yorks. m. (1) by Apr. 1414, Agnes, da. of Roger Flore* by his 1st w.; (2) by c.1418, Isabel (b.1402), da. and h. of Aubrey Wittlebury (d.1406) of Wittlebury in Whissendine, Rutland by his w. Margery; wid. of a s. of Roger Flore, 1s.; 1s. illegit. Kntd. by Jan. 1420.
Offices Held

Attestor, parlty. elections, Rutland 1419, 1421 (May), 1423, 1426, 1429.

Commr. Rutland Apr. 1421 – Aug. 1450; of gaol delivery, Oakham May 1444.1 C66/458, m. 28d.

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.

Address
Main residence: Burley, Rutland.
biography text

More may be added to the earlier biography.2 The Commons 1386-1421, iv. 86-88.

A great deal of material about Pleasington’s career is provided in the lengthy Chancery pleadings in an action sued by his widow against one of his executors, William Anderby*, in 1455.3 C1/16/647. This reveals that he was first a ward of Queen Joan, who sold both the custody of his lands and his marriage to Roger Flore for 500 marks, and that, as an adolescent, he entered the service of Philip Repingdon, bishop of Lincoln. Through the bishop’s intervention, the queen granted him livery of his lands two years before his coming of age. He then embarked on a military career: in June 1417 he mustered in the retinue of Sir William Bourgchier†, and fought under Humphrey, duke of Gloucester in 1421.4 E101/51/2, m. 23; C76/104, m. 12. The pleadings provide new details about Pleasington’s last years when he conceived the notion of departing on pilgrimage to Rome and Jerusalem. In preparation he conveyed his Yorkshire property, including the manor of Ilkley, to his cousin, Henry Vavasour of Hazlewood, Sir John Neville, brother of Ralph, earl of Westmorland, and others lesser men in the pleadings. It soon became apparent, however, that he would not himself be able to attempt the journey, and he thus left instructions that these feoffees employ the profits of the property to find five priests to sing for his soul at the Scala Celi in Rome and five men to travel to Jerusalem and other holy places. On the expiry of a certain term the property was to pass to his heir, save the manor of Ilkley, which was to be sold in accordance with the wishes of his grandfather, Sir Robert Pleasington (d.1393), chief baron of the Exchequer. The Chancery action arose of the self-interested attempt of Sir Henry’s widow Isabel to prevent the sale.

Isabel was a woman of considerable wealth even without the manor of Ilkley, and the petition provides a new detail about her marriage to Sir Henry. Roger Flore, having paid so heavily for the young Henry’s marriage, contracted him to his daughter Agnes, but she soon died, and so he married him to Isabel, who was the widow of one of his sons (probably William). In doing so, he added significantly to his ward’s material prosperity, for Isabel was a considerable heiress. Aside from the Rutland property specified in the earlier biography, she was also able to establish her title to the manor of Thorpe just across the border in Northamptonshire. This had been one of three manors – the other two lying nearby at Marholm and Milton – which Sir William Thorpe† had granted to her grandfather, John Wittlebury† (d.1400), and by a fine levied in 1395 all three were settled on Wittlebury’s male issue by his second wife, Agnes. Since Isabel was Wittlebury’s grand-daughter through his first wife these manors did not form part of her inheritance. For reasons that are unclear, however, Richard Wittlebury, the only one of Agnes’s sons to have issue was omitted from the entailment made in the 1395 fine in respect of the manor of Thorpe, and thus our MP and Isabel were to win that manor in an action sued in 1424 against Thomas Sutton, the guardian of Richard’s son and heir, John.5 The Commons 1386-1421, iv. 883; CP40/654, rot. 304; Northants. RO, Fitzwilliam (Milton) Ch. 1408. His wife’s lands made Pleasington a wealthy man: he was assessed on an annual income of as much as £160 to the subsidy of 1436.6 E159/212, recorda Hil. rot. 14 (i)d.

After Pleasington’s death Isabel seems to have retired to the care of the Benedictine nuns of St. Michael, Stamford. She was certainly there in November 1457, when she quitclaimed her property at Empingham (Rutland) to a yeoman, Richard Galway, who was both her servant and one of our MP’s executors. Earlier, in September 1453, she had named Galway as her attorney to deliver seisin of her late husband’s manors at Healaugh and Reeth in Swaledale (Yorkshire) to feoffees headed by Henry, Lord Scrope of Bolton, as part of the arrangements for the marriage of her son, William Pleasington, to Lord Scrope’s daughter.7 Lincs. AO, Earl of Ancaster mss, 3ANC1/34/1/6-7. According to an inquisition taken in January 1471, she died on 1 Jan. 1461, although this may be an error for 1471.8 C140/33/43.

Other incidental references to Pleasington document his connexions in the Midlands. In May 1439 he was named as a feoffee for the performance of the will of his Rutland neighbour, Sir John Basings of Empingham, and as such was responsible, in October 1447, for making a contentious release to Sir John’s sister and heiress, Alice, widow of Thomas Makworth* of Mackworth (Derbyshire), who had been implicated in the murder of Sir John’s bastard son a year earlier.9 S.J. Payling, ‘Murder, Motive and Punishment’, EHR, cxiii. 7-8; C139/122/41; CIMisc. viii. 206. It was no doubt through Alice that our MP became connected with the Makworths: at an unknown date between about 1430 and 1451 he surrendered Barnard’s Inn, his property in Holborn, to her brother-in-law, John Makworth, dean of Lincoln cathedral.10 E. Williams, Early Holborn, ii. nos. 1063-4. More mundanely, on 27 Feb. 1449 he headed the list of witnesses to the deed by which Richard, duke of York, granted the valuable manor of Hambleton to feoffees acting for Ralph, Lord Cromwell.11 KB27/752, rot. 32.

Pleasington was indirectly involved in another murder aside from that of Basings’ bastard. According to an indictment taken at Ketton before Thomas Stokes, one of the Rutland coroners, on 23 Oct. 1449, one Thomas Bermyger had been murdered a few days before at our MP’s house at Whissendine. The alleged murderers were servants of our MP’s neighbour, Sir Laurence Berkeley*, and it is tempting to think that the crime arose out of a dispute between the two knights. But other evidence shows that Bermyger was killed because he was a servant of Everard Digby*, then involved in a violent quarrel with Berkeley’s friend, John Chiselden*. Digby, like our MP, held a manor in Whissendine, and presumably Bermyger was killed as he fled from Digby’s property. There is, in any event, no evidence that our MP was himself involved in the dispute.12 KB27/766, rex rot. 5d; SC8/96/4800; CP40/771, rot. 322; VCH Rutland, ii. 160.

Author
Notes
  • 1. C66/458, m. 28d.
  • 2. The Commons 1386-1421, iv. 86-88.
  • 3. C1/16/647.
  • 4. E101/51/2, m. 23; C76/104, m. 12.
  • 5. The Commons 1386-1421, iv. 883; CP40/654, rot. 304; Northants. RO, Fitzwilliam (Milton) Ch. 1408.
  • 6. E159/212, recorda Hil. rot. 14 (i)d.
  • 7. Lincs. AO, Earl of Ancaster mss, 3ANC1/34/1/6-7.
  • 8. C140/33/43.
  • 9. S.J. Payling, ‘Murder, Motive and Punishment’, EHR, cxiii. 7-8; C139/122/41; CIMisc. viii. 206.
  • 10. E. Williams, Early Holborn, ii. nos. 1063-4.
  • 11. KB27/752, rot. 32.
  • 12. KB27/766, rex rot. 5d; SC8/96/4800; CP40/771, rot. 322; VCH Rutland, ii. 160.