Churchill, Sir Winston (1620–88), politician, was baptised on 18 April 1620, eldest surviving son of John Churchill, deputy registrar of chancery, of Whootton Glanville, Dorset, England, and his first wife, Sarah Winston of Standistone, Gloucestershire, daughter and coheir of Sir Henry Winston. He entered St John's College, Oxford, in 1636 (but took no degree) and Lincoln's Inn in 1637. Churchill took the royalist side in the civil wars, serving as a captain of horse (1643–5). On 26 May 1648 he married Elizabeth Drake of Ashe, Devonshire, niece of George Villiers, duke of Buckingham. They had seven sons and four daughters. Of these, John Churchill (qv) later became duke of Marlborough, while Arabella Churchill became a mistress of James (qv), duke of York, with whom she had a son, James Fitzjames (qv), later duke of Berwick.
Called to the bar in June 1652, as a royalist Churchill was forbidden to practise. Financial hardship ensued, and he spent most of the 1650s living with his wife's relatives. After the restoration he regained his estate of Wootton Bassett in Wiltshire. Appointed to a number of minor offices, in 1661 he was elected MP for Weymouth. Inactive in the constituency, he was very active in parliament. Patronised by Sir Henry Bennett, later earl of Arlington, Churchill became a valuable if tactless parliamentary manager for the government. In November 1662 he was involved with Col. Richard Talbot (qv) in attempting to obtain the Clanmalier estate for Bennett. Soon afterwards he was appointed a commissioner of settlement (court of claims) for Ireland.
Churchill took an active role in the workings of the court of claims from the beginning, establishing a close relationship with Talbot. Opposed to former Cromwellians, he was compromised by his continual manoeuvres on Bennett's behalf, some of which involved lands claimed by Henry Jones (qv), bishop of Meath. In September 1663 he was regarded as one of the three commissioners loyal to the king's interests. Acutely and consistently aware of the security implications of the land settlement, Churchill sought to ensure that the restoration of figures such as Randal MacDonnell (qv), marquis of Antrim, Ulick Burke (qv), earl of Clanricarde, and Donough MacCarthy (qv), earl of Clancarty, did not encourage further claims by the discontented. However, he himself had adjudicated in Antrim's favour, and they were briefly neighbours in Dublin after the verdict was reversed. Assiduous in his role, in October 1663 Churchill was active in drafting a bill of explanation (of the 1662 act of settlement). In January 1664 he was knighted. In 1664 he was also made a fellow of the Royal Society, and was appointed clerk comptroller of the green cloth in the king's household, despite the objections of James Butler (qv), duke of Ormond. In 1665 he opposed the Irish cattle bill in Westminster, and in 1666 was appointed to the second court of claims to execute the act of explanation and the remaining clauses of the act of settlement. He returned to England on the court's adjournment in May 1667, but was back in Ireland by October. In 1668 he apparently assaulted Robert Thornhill, an agent of the duke of York in Ireland, over claims that York had been told that Churchill was his strongest opponent amongst the commissioners. In 1669 he sought to obstruct the charges brought against Roger Boyle (qv), earl of Orrery, in the English parliament.
Churchill lost favour in the 1670s, being both quarrelsome and intimately associated with the court. In 1675 he published Divi Brittanici, which among other things offered a staunch and unpopular defence of the tax prerogatives of the crown. Churchill himself did not profit significantly from his career, and suffered financial hardship in later life: in January 1678 he was seeking repayment of £700 from Ormond. He lost his office in the king's household in 1679, but was soon restored, and retained it until his death. In 1685 he was elected MP for Lyme Regis. Churchill died 26 March 1688, and was buried in St Martin-in the-Fields, Westminster.