The Skeffingtons took their name from a village ten miles east of Leicester, where they were settled by the mid-thirteenth century.
Skeffington spent more than two years at the Middle Temple, but not necessarily in study, being twice fined for missing readings and once for being absent at Christmas.
In November 1613 the Leicestershire branch of the family was threatened with extinction. Sir William Skeffington had died in 1605, leaving his estate to his brother John, who disliked the fact that Sir William’s widow, Lady Katherine, subsequently married her groom, Michael Bray. When John and Bray met at a tavern in 1613, they fought and killed each other.
Skeffington probably owed his election for Newcastle-under-Lyme in 1626 to his brother-in-law Sir William Bowyer II*. Sir William’s father, John Bowyer, had sat for the borough in 1597 and 1604, and the Bowyers were significant landowners in north-west Staffordshire, their holdings including property in Newcastle. Skeffington’s candidacy may also have been supported by Staffordshire’s lord lieutenant, the 3rd earl of Essex. Skeffington’s father was alleged to have been one of the ‘frequenters’ of the 2nd earl of Essex in 1601, and the 3rd earl may have been responsible for the election of Skeffington’s brother, Sir Richard, at Tamworth in 1625.
Skeffington seems to have become disillusioned with Parliament. In a letter, evidently written after 9 May, he reproached his kinsman Sir Edward Dering* for not warning him to avoid election, describing the Commons as a place ‘to please none, to displease all and bear all his own charges’.
After the death of Francis Staresmore* on 8 May 1626, Skeffington took over the latter’s task of keeping the 5th earl of Huntingdon, the lord lieutenant of Liecestershire, informed of parliamentary proceedings.
Skeffington declared himself Buckingham’s servant in an undated letter of thanks addressed to Sir Edward Dering and endorsed ‘about the baronetship’.
In 1635 Skeffington inherited his father’s Staffordshire estates, and was subsequently described as being of Fisherwick. This substantially increased his annual income, which in 1651 he put at £1,280.
By January 1639 Skeffington was a gentleman of the privy chamber.
Skeffington was buried at Skeffington on 20 Nov. 1651, where his funeral monument stands. He left no will and consequently administration was granted to his wife on 23 June 1652.
