Background
Whitehead was the son of Sir Henry Whitehead of Norman Court Hampshire and his wife Constance.
Whitehead was the son of Sir Henry Whitehead of Norman Court Hampshire and his wife Constance.
He was educated at Brasenose College, Oxford (1610) and was awarded Bachelor in 1612. He studied law at the Inner Temple in 1613 and travelled abroad between 1614 and 1617.
He fought for the Parliamentary army in the English Civil War. Whitehead inherited the family estates at Shirley and Hill on the death of his father in 1629. In 1635 he was appointed High Sheriff of Hampshire when he had the task of collecting ship money for the county.
He wrote to the council complaining of the backwardness of the county, and imprisoned a constable who failed to certify the defaulters and who argued that the money "would never be gathered during his lifetime".
Nevertheless, he was ordered to collect the arrears, which stood at £404. He was re-elected Member of Parliament for Hampshire for the Long Parliament in November 1640.
Whitehead became a faithful adherent of Parliament during the Civil War, possibly soured against the King"s cause because of his experience with collecting Ship money. He was one of the colonels of regiments in the Parliamentary army of Hampshire and Sussex, together with Richard Norton, Onslow, Jarvis, and Morley.
In 1643 Whitehead was one appointed to extract large sums of money from Royalists on pain of imprisonment at Portsmouth, and is said to have remarked that he "had been at a great charge to build a cage at Portsmouth where many Hampton birds should sing very suddenly." Under the command of General Waller he was present at siege of Basing House at the beginning of 1644.
He also besieged Bishop"s Waltham Palace, and obtained its surrender with the help of Major-General Browne"s London brigade. He was given permission "to pull down the house if he chose." In June 1644 the House of Commons instructed him and others to sequestrate the estates of Papists and delinquents valued at less than £12,000 within London and Westminster in order to pay off arrears to the garrisons of Portsmouth and of Hurst Castle, Southsea Castle and Calshot Castle.
Short Parliament]
In 1628 he was elected Member of Parliament for Lymington and sat until 1629 when King Charles decided to rule without parliament for eleven years. In April 1640, Whitehead was elected Member of Parliament for Hampshire in the Short Parliament.
