Thomas Chicheley (1618-1699) came from a distinguished and wealthy Cambridgeshire family. He was sixth in descent from Henry Chicheley who bought Wimple or Wimpole in the county, and eighth in descent from William Chichele, Sheriff of London, a younger brother of Henry Chichele, Archbishop of Canterbury and founder of All Souls College, Oxford. Thomas Chicheley served as High Sheriff of Cambridgeshire and also represented the county in the House of Commons from 1640 to the Long Parliament. As a staunch Royalist he was banned from sitting in Parliament in 1642, and probably followed the King to Oxford where he had established his temporary court. He was a member of the Oxford Parliament and was probably the 'Thomas Chisley' who signed the surrender of Oxford in 1646. He was heavily penalised financially during the Commonwealth, but at the Restoration, he was re-elected Member of Parliament, and made Master-General of the Ordanances. On 10 June 1670 he was knighted and became a Privy Councillor. His fortunes too seem to have been restored to him following Charles II's return to the throne, and Pepys records him living in great style at his London house in Queen Street, Covent Garden. However, such was his extravagence that he was forced to sell his estate in Cambridgeshire in 1686 to Sir John Cutler. He contined to sit as Member for Cambridgeshire in 1678-9, 1685 and 1689, and died at the age of eighty-one in 1699.

As Dr Malcolm Rogers notes in the entry for this painting in the Dobson exhibition, the artist has clearly studied Van Dyck's Portrait of Thomas Killigrew (Earl of Bradford) for the pose and treatment of the sitter. By 1643 Dobson was established as Court-Painter to Charles I following the deaath of Van Dyck, although how he had achieved this role is uncertain. In the early 1640's the King had moved his court to Oxford, and Dobson went too, living the cosmopolitan atmosphere of St. Martin's Law, and establishing his studio in the High Stret near St. Mary's Church. Conditions were extremely harsh in the City, with the large number of officers, soldiers, their families and servants living in close and cramped quarters. Chicheley probably came to Oxford in 1642 and like many other military commanders, followed the Royal example by having his portrait painted. The nature of life in the City made the task of acquiring artist's material extremely difficult, and most of the portraits dating from this time were painted on small coarse canvases which he had primed by his assistant Mr Hesketh. Typically the present picture is on three pieces of canvas stitched together.

A copy of this portrait is at Narford and another appeared as lot 29 in the Earl of Oxford's sale, 11 March 1742 (15s. to Coleraine); 'Mr Chicheley's Head with a Band, by Dobson, 3 gns'.