Skipwith’s ancestors were landholders in Lincolnshire in the fourteenth century and first produced a knight of the shire in 1406. His father, the youngest of five sons and a royal equerry, acquired property in Leicestershire, including the manor of Cotes in the parish of Prestwold, near the border with Nottinghamshire, and represented Leicester in two Elizabethan parliaments.
It was probably with the support of the 4th earl of Huntingdon (George Hastings†) that Skipwith was elected for Leicestershire in 1601. In 1604, however, Huntingdon urged the corporation of Leicester to elect Sir John Pulteney*, the nominee of the chancellor of the Duchy of Lancaster, Sir John Fortescue*. Skipwith was nominated by the borough’s puritan recorder Augustine Nicolls, and was made free of the borough shortly before the election.
Skipwith was named to 26 committees and made 11 recorded speeches before his death in the middle of the fourth session. In 1604 he was appointed to committees to consider restitution bills for the earls of Southampton, Essex and Arundel (2 Apr.) and for Lord William Howard (15 May).
In January 1605 Skipwith signed a letter from the Leicestershire gentry to Viscount Cranborne (Robert Cecil†) on behalf of those ministers threatened with deprivation for refusing to subscribe to the 1604 Canons. Despite his undoubted protestantism, he was related to one of the Gunpowder plotters, Sir Everard Digby, who was the son of Skipwith’s half sister. It is not known whether Skipworth had returned to Westminster by the time the Gunpowder Plot was discovered, but the following January he wrote to Sir John Grey*, asking him to alert Cranborne, by now earl of Salisbury, to the allegedly suspicious activities of the Catholic Sir Henry Hastings of Braunston.
In the second session Skipwith was appointed to the committee for a bill to assure the jointure of his first wife’s sister-in-law, Dame Eleanor Cave (22 Jan. 1606).
Skipwith may have spoken in the debate on the bill against poaching on 26 April.
In the third session Skipwith made only one recorded speech, on 7 May 1607, in which he proposed, probably with Sir Robert Wingfield in mind, to ask the king to identify those responsible for supplying him with misleading reports of debates. However, this seemed to most Members ‘as if he would have His Majesty become an accuser’, and consequently his motion was rejected to shouts of ‘no, no’.
In April 1608 Skipwith obtained an order from the treasurer of the Household Lord Knollys (William Knollys†) to the Leicestershire magistrates to inquire into the ‘intolerable abuses’ of Christopher Walton, the board of Greencloth’s unpopular purveyor in the county ‘to the impoverishment of some poor inhabitants’. However, this seems to have only resulted in an ineffective undertaking from Walton that he would not charge excessive fees. There were renewed complaints against Walton three years later.
On returning to Westminster for the fourth session, Skipwith queried on 26 Feb. whether it was necessary to obtain the concurrence of the Lords in pursuing Dr. Cowell for the high prerogative views expressed in The Interpreter.
Skipwith died in London on 3 May, and was buried at Prestwold four days later. In his will dated 15 May 1604, to which a codicil was added on 29 Oct. 1607, he bequeathed one third of his estate to his eldest son Henry, the remainder being devoted to provide £600 for his widow, £3,500 in portions for his daughters, and annuities of £30 each to his two younger sons. His widow set aside £150 to erect a splendid monument for him, with an epitaph written by Sir John Beaumont of Gracedieu which described his some who ‘when need requires, with courage bold / To public ears his neighbours’ griefs unfold’. Sir William Heyricke, who served as Skipwith’s colleague in the Commons from 1605 onwards, wrote in 1614 that ‘Leicestershire got as good an opinion in the House last Parliament by Sir William Skipwith and Sir Thomas Beaumont the elder as any shire or county in England’. His son was created a baronet in 1622, took the royalist side in the Civil War, and was compelled to sell out to the London alderman Christopher Packe†. The family did not re-enter Parliament until Sir Gray Skipwith was elected for Warwickshire in 1831.
