Littleton was descended from Richard Littleton, the second son of Sir Thomas Littleton, the fifteenth-century judge and legal author. Richard inherited property in Warwickshire and Shropshire and married the heiress of the Pillaton estate in the parish of Penkridge, six miles south of Stafford.
Littleton was educated at the Inner Temple, and married, in 1573, Margaret, daughter and co-heiress of Sir William Devereux, younger brother of the 1st earl of Essex. Following his father’s death in July 1574 he inherited, on paper at least, an impressive estate: 16,000 acres in and around Penkridge, 600 more elsewhere in Staffordshire, 1,400 acres in Warwickshire, 900 acres in Shropshire and 940 acres in Worcestershire. However, the Warwickshire and Shropshire properties, and a substantial part of the lands in Staffordshire, formed part of the jointure of his mother, who survived until 1602. Moreover, Littleton’s father had placed Teddesley Hay, part of the Penkridge estate, in the hands of trustees for 21 years to pay his debts, legacies and funeral charges, while other parts of the estate were charged with annuities for the benefit of his younger sons.
In 1605 Littleton claimed that he had been a Staffordshire magistrate for 30 years, but he seems not to have joined the bench until the early 1580s.
From the late 1580s Littleton was closely associated with the 2nd earl of Essex, who in July 1588 procured a brace of bucks for Littleton from Paget’s confiscated estates and frequently employed Littleton on business concerning his estates or servants in Staffordshire.
Following Essex’s rebellion Littleton was arrested and accused of involvement in the uprising. Littleton, however, claimed that he had been overtaken by Essex and his supporters while going to hear a sermon at Blackfriars, and that, though forced to accompany them to Cheapside, had taken refuge in a linen draper’s shop when he heard that Essex had been declared a traitor.
Littleton stood for Parliament again in 1604, by which time he was living at Pillaton Hall. However, he was challenged by Sir Walter Harcourt†, who had twice sat for Staffordshire. Littleton had supported Harcourt for a county seat in 1593, and had subsequently become his surety, but the two men had fallen out, as Harcourt believed that Littleton was conspiring with his creditors.
By 1605 Littleton was described as being of Merevale, the Warwickshire home of his former father-in-law, which he may have acquired after the death of his brother-in-law, Sir Edward Hastings†, in about 1603.
On 19 Oct. 1610 the Commons ordered a by-election after receiving a certificate from the principal inhabitants of Staffordshire that Littleton was incurably ill.
