Sir Henry Sidney (1529 – 5 May 1586), Lord Deputy of Ireland, was the eldest son of Sir William Sidney of Penshurst, a prominent politician and courtier during the reigns of Henry VIII and Edward VI, from both of whom he received extensive grants of land, including the manor of Penshurst in Kent, which became the principal residence of the family.
Henry Sidney was brought up at court as the companion of Prince Edward, afterwards King Edward VI, and he continued to enjoy the favour of the Crown, serving under Mary I of England and then particularly throughout the reign of Queen Elizabeth I. He was instrumental in the Elizabethan conquest of Ireland, serving as Lord Deputy three times. His career was controversial both at home and in Ireland.
Born to Anne Pakenham (b. 1511 - d. 22 October 1544) and Sir William Sidney of Penshurst (b. 1482 - d. 11 February 1553), Sidney married Mary Dudley, eldest daughter of John Dudley, 1st Duke of Northumberland, in 1551. They would have three sons and four daughters. His eldest son was Sir Philip Sidney, and his second was Robert Sidney, 1st Earl of Leicester.
His daughter Mary Sidney married Henry Herbert, 2nd Earl of Pembroke, and by reason of her literary achievements was one of the most celebrated women of her time.
In 1556 Sidney served in Ireland with the Lord Deputy, Thomas Radclyffe, 3rd Earl of Sussex, who in the previous year had married his sister Frances. Both served Queen Mary until her death in 1558. Sidney had a large share in expanding the English administration in the country, which had shrunk over the centuries to the area around Dublin known as the Pale. He was also involved in the civil and military measures taken by his brother-in-law for bringing Irish chieftains into submission to the English Crown, known as Surrender and Regrant. In the course of the Lord Deputy's expedition to Ulster in 1557 Sidney devastated the island of Rathlin. In the following year, during the absence of Sussex in England, he had sole responsibility for the government of Ireland and conducted himself with marked ability. A second absence of the Lord Deputy from Ireland, on the accession of Queen Elizabeth, threw the chief control into Sidney's hands at the outbreak of trouble with Shane O'Neill, and he displayed great skill in temporising with the chieftain until Sussex reluctantly returned to his duties in August 1559. About the same time Sidney resigned his office of vice-treasurer of Ireland on his appointment as president of the council of the Marches in Wales, and for the next few years he resided chiefly at Ludlow Castle, with frequent visits to the court in London.