He became a Member of Parliament, a shipowner and shipbuilder during the reign of Elizabeth I. One of his ships, the Leicester sailed with Sir Francis Drake against the Spanish Armada. A wealthy landowner, Sir Henry is known to have played an active role in the Plantations of Ireland and was knighted by the Lord Deputy of Ireland in 1593.
He was the son of Sir Anthony Ughtred and Elizabeth Seymour, sister to Jane, the third wife of Henry VIII. After 1557 he married Elizabeth Paulet, the daughter of John Paulet, 2nd Marquess of Winchester and widow of Sir William Courtenay.
His father died in Jersey on 6 October 1534 and was buried in the chapel of St George, at Mont Orgueil. After her husband's death Elizabeth returned to Yorkshire. The manor of Kexby had been granted for life to Sir Anthony and his wife by Henry VIII in 1531 and it was here that Henry's sister Margery was born.
Ughtred married Elizabeth, daughter to John Paulet, 2nd Marquess of Winchester and the widow of Sir William Courtenay, who was killed at the Battle of St Quentin in 1557. Elizabeth died in 1576 and Ughtred remarried, however the identity of his second wife is unknown.
After the death of his step-father in 1576, Ughtred was involved in a long-running and bitter dispute with his step-brother, William Paulet, 3rd Marquess of Winchester, who accused him, as an executor of his father's will, of maladministration of the property and failure to settle the claims of a number of tenants and servants.
Paulet took the matter to William Cecil, 1st Baron Burghley and in June 1582 Ughtred wrote to Lord Burghley, to defend himself, complaining of "hard words", which Burghley had used to him in the Star Chamber. He maintained that the Marquess’s accusations were unjust and informed Burghley that he was now virtually a prisoner in his own house and that he had been engaged on the case for seven months, which had cost him over £1,000 to the great hindrance of his "private causes", and waste of precious time.
The following year he was imprisoned for several months in the Fleet Prison over the same matter. Early in 1586 the dispute came before the House of Lords, where the question of the jointure of the Dowager Marchioness was examined, and Ughtred gave evidence about his executorship. Paulet pursued the matter relentlessly for a number of years, and in 1596, out of malice, persuaded the Privy Council to dismiss Ughtred from the captaincy of Netley Castle on the ground that his long absence in Ireland had caused him to neglect his charge.
Ughtred was a justice of the peace in Hampshire from 1575 until about 1593, sheriff in Hampshire from 1581 to 1582, a member of the council of Munster in 1587 and captain of Netley Castle, Hampshire before 1596.
Ughtred was elected as a Member of Parliament for Marlborough in 1584 and for Great Bedwyn in 1589. He undoubtedly owed his parliamentary seats to Seymour influence. His first cousin, Edward Seymour, 1st Earl of Hertford was Lord of Marlborough, and at this period also dominated elections at Great Bedwyn, where Ughtred’s co-Member in 1589 was another cousin, John Seymour.
On 15 February 1585 Ughtred served on a conference with the Lords concerned ostensibly with fraudulent conveyances, but in reality was concerned with relations between the House of Lords and the House of Commons.
He was named On 5 March to a Commons committee concerned with the poor law, and on 11 March he was appointed, with his half-brother Thomas Cromwell and Sir William More, to examine a currier accused of making defamatory statements about the House’s treatment of a bill concerning tanners.
He spoke in the debate on the bill against rogues and vagabonds in this Parliament, maintaining that large sums were being laid out to little purpose on houses of correction. He opposed the return of vagabonds to their own parish, where they had to be supported by the inhabitants of "poor villages and hamlets" who had "already more of their own than they have work for".
In the Parliament of 1589 Ughtred served on the subsidy committee on 11 February, and he spoke on the bill about captains and soldiers as well as serving on the committee on 26 February. The next day he was named to a conference with the Lords on the same lines as that of 15 February 1585. This time the subject was the Queen’s dislike of the purveyors bill.
Shipowner and shipbuilder
As a shipowner, Ughtred knew that sailors who had been paid off after a voyage ran a risk of becoming unemployed and classed as vagabonds. Southampton, where he lived for several years, had experienced this problem in the early 1580s. Ughtred was well aware that ships were sometimes left to rot in the harbour because the owners could not pay the cost of repairs. In August 1582, Henry Knollys informed Sir Francis Walsingham that a Breton ship he had brought into Hampton had remained there for four years without being claimed. Knollys had then given her to Ughtred, who had no sooner had her repaired than the former owners demanded her back.
The embargo on sending ships to sea, following Philip II of Spain’s acquisition of Portugal, would have involved Ughtred in serious loss had he not been allowed, "in consideration of his great charges sustained in building of sundry ships and furnishing of them to the seas", to send out the Galleon, the Elizabeth and the Joan.
A licence he had received to export 500 quarters of wheat to Portugal was cancelled owing to the political situation, however he was permitted to send the same amount to Ireland.
In 1582 one of his vessels, the Ughtred or Bear, valued at £6,035, acted as flagship to Edward Fenton’s unsuccessful voyage, and was renamed the Leicester, presumably in honour of Robert Dudley, 1st Earl of Leicester, the principal shareholder in the adventure. The Leicester sailed with Sir Francis Drake in 1585-6, and was one of his west-country squadron against the Spanish Armada, later possibly taking part in Thomas Cavendish’s last voyage.
Some of Ughtred’s other ships were engaged in voyages to the west. In 1582 he petitioned the Privy Council claiming compensation for losses he had sustained in Spain and the Caribbean.
Ughtred was involved in a number of lawsuits as a result of his trading ventures. In November 1582 the Spanish ambassador informed Lord Burghley that "a ship or two", owned by Mr Ughtred of Southampton, had robbed off Newfoundland more than 20 ships belonging to the King of Spain, and that the Admiralty court had awarded one of these, "laden with fish and grease", to Ughtred, his ships having brought her into Bristol.
Over a year later Francisco Hernandez of Viana, was still attempting to get compensation for this or another attack on Portuguese ships off Newfoundland.
Landowner in Ireland
Sir Henry Ughtred was one of the many men who were to profit from the Plantations of Ireland, the confiscation of land from rebellious Irish landowners by the English crown, and the colonisation of this land with settlers from England and Wales. Ughtred's investments in Irish lands would also prove to be a further source of litigation.
In 1586 he was granted a licence, with his step-son Sir William Courtenay and others, to "undertake the counties of Connoll and Kerry in one consort". The company was headed by Courtenay, but Ughtred had a considerable stake in it. Unfortunately for the "undertakers", some of the lands in Munster which they were allotted were claimed by Irishmen who were not in rebellion, and the consequent lawsuits were a constant drain on any profits made by the enterprise. In 1591 Ughtred gained a Privy Council decision in his favour over some of the property assigned to him, but two years later it was rescinded, and in 1597 the matter remained unresolved.
On 5 October 1598, Sir Henry Ughtred and his wife fled their Irish home and were attempting to reach safety in Limerick, 15 miles away. Three days later his manor was burnt by Irish rebels and his castles of Meane, Pallice and Ballenwylly were reported to have been abandoned. George Ughtred Courtenay, a son of Sir William Courtenay inherited the Manor of Meane , which was left to him by his uncle, Sir Henry Ughtred, "on his taking the name of Ughtred." Sir Henry Ughtred and his wife appear to have died in Ireland around this time as no further reference to them has been found.