He was the fourth son of John III Killigrew of Arwenack, the first Governor of Pendennis Castle, of an old Cornish family, by his wife Elizabeth Trewenard, second daughter of James Trewenard of Trewenard. He was probably educated at Cambridge, but there is no definite information on the point. Killigrew served as a gentleman in the household of John Dudley, Duke of Northumberland, and became a lifelong follower of the Dudleys. On 18 February 1553 he was returned member of parliament for Newport-juxta-Launceston. He assisted Sir Peter Carew in escaping to the continent in January 1554, and during the remainder of Queen Mary of England's reign appears to have been in exile. Killigrew was at Paris in July 1556, when he was described by the English authorities as a rebel. From a French base, he and his brother Peter engaged in piracy. In August 1557, Henry was present at the Battle of St. Quentin, where Sir James Melville stated of him that "Harry Killygrew, an Englis gentilman, my auld friend," held his horse while he got his wound dressed after his escape. Killigrew was recalled to England on the accession of Elizabeth, and she employed him on various diplomatic missions, including one to Germany in connection with negotiations for a defensive league. In July 1559 he went for a short time to assist Nicholas Throckmorton in France. Killigrew counted both Robert Dudley, Earl of Leicester and William Cecil, Lord Burghley as his patrons. He wrote to Dudley in 1562, regarding their Prostestant policies: "In these cases I take you to be as one". In July 1562 he led a military contingent at Rouen, as part of the Newhaven expedition. In June 1566 he was sent on a mission from Elizabeth to Mary, Queen of Scots, for the 'declaration of sundry things necessary to be reformed between them for the preservation of their amity'. He returned in the following July, and after the murder of Darnley was again sent to Scotland with a special message to the Queen of Scots, which he delivered to her 'in a dark chamber.' On 20 April 1572 he was elected M.P. for Truro. In September, shortly after the St. Bartholomew's Day Massacre, he was again sent to Scotland, in connection with the negotiations for the surrender of the Queen of Scots to the Protestant lords, who would then immediately execute her. This was a scheme so secret that, apart from Killigrew, only Queen Elizabeth, Cecil and Leicester were privy to it on the English part. Due to the Earl of Mar's sudden death, nothing came of it. Killigrew ultimately succeeded in persuading Elizabeth to send an English force to assist in the siege of Edinburgh Castle, and in numerous letters to Burghley minutely described the siege, and the negotiations, some involving Nicolas Errington, connected with its surrender. After Edinburgh Castle fell in June 1573 he negotiated the removal of cannon from Hume Castle and the keeping of jewels belonging to Mary, Queen of Scots, including the "Great H of Scotland" disputed by Agnes Keith and Regent Morton. Morton gave him a gilt and engraved silver basin, three covered cups, a silver salt, and a gold ring. A year later he reported that Regent Morton had discovered a letter from William Kirkcaldy of Grange the defeated and executed commander of the castle, to Mary, Queen of Scots, in which he listed the locations of the jewels she had left behind in Scotland, and that William Drury, Marshall of Berwick, had taken some jewels in pledge for a loan of £600. In August 1574 he was approached by the Flemish mining entrepreneur Cornelius de Vos, who wanted to negotiate with William Cecil. Killigrew was sent back to Scotland in May 1575 to discuss with Regent Morton Elizabeth's refusal to make a formal mutual league with Scotland, pensions for the Regent and the nobility, and the custody of Mary, Queen of Scots. Subsequently, he was employed in similar diplomatic missions in Scotland, Germany, France, and the Low Countries. The Treaty of Nonsuch gave the English crown the right to designate two councillors to the Dutch council of state. Killegrew served as an English Councillor on the Dutch Council of State in 1586, and again in 1587–1589. While in attendance on the Earl of Essex in France he was knighted on 22 November 1591. He was the first in England to write political memoirs to highlight and defend his actions during his career as a public servant. He died in the spring of 1603, his will having been proved on 16 April.
Artistic activities
praises Killigrew in his Worthies for his learning and his artistic accomplishments. He states that, while a good musician, he was especially skilled as a painter, being "a Dürer for proportion... an Angelo for his happy fancy, and an Holbein for oyl works", but no authenticated work of his brush is known. Killigrew gave £140 to Emmanuel College, Cambridge, for the purchase of St. Nicholas Hostel, the materials of which were applied to the construction of the lodge for Dr. Laurence Chaderton, the first master. His London residence was in Lothbury.
Family
Killigrew lived in Hanworth in Middlesex and Falmouth in Cornwall. On 4 November 1566 Killigrew married in the church of St Peter Le Poer, London, Catherine, fourth daughter of Sir Anthony Cooke and Anne Fitzwilliam. He thus became Cecil's brother-in-law. His wife died in 1583, and on 7 November 1590 he was married in the same church to Jaél de Peigne, a French Hugenot. She was naturalised in June 1601. After Henry's death she remarried on 19 April 1617 George Downham, Bishop of Derry, and died c.1632. By his first wife, Killigrew had four daughters:
By his second wife, he had a daughter and two sons:
Jane
Joseph
Henry
Joseph, ten years old at his father's death, succeeded to his estates.
In fiction
He is a major character in the historical novel The Grove of Eagles by Winston Graham, which shows him in a generally sympathetic light. The novel turns largely on the declining fortunes of his nephew John Killigrew of Arwenack, who looks in vain to his uncle's influence to protect him from bankruptcy. Henry is portrayed as one of the few advisers whom the Queen really trusts: "as close to her as a Father Confessor". Another character notes that while many courtiers come and go, a few like Henry serve the Queen decade after decade. His second marriage to Jael de Peigne is shown as being somewhat troubled, as his beautiful and much younger wife is discreetly unfaithful to him.