Docwra (Dowkra, Dockwra, Dockwraye, Dockquerye, Docura), Sir Henry (1564–1631), 1st baron of Culmore , soldier and administrator, was baptised on 30 April 1564, younger son of Edmund Docwra of Chamberhouse manor, Thatcham, Berkshire, England, and his wife Dorothy. He joined the army c.1582–3 and may have served under Sir Richard Bingham (qv) in Connacht in the mid 1580s. Later in life, he wrote an account of Bingham's military campaigns against Irish rebels in Mayo in a manner that suggests he had witnessed these events. In c.1590 he went to France to serve in the English army under his patron Robert Devereux (qv), 2nd earl of Essex. By 1591 he was a captain and spent most of the 1590s serving in France, the Low Countries, and on the expedition to Cadiz in 1596, where Essex knighted him. Docwra was constable of Dungarvan Castle from 20 September 1594 to 18 April 1597, but he does not appear to have gone to Ireland during that time. On 1 March 1599 he arrived in Ireland with his regiment and campaigned with Essex that year in Leinster, Munster, and Ulster as a colonel. The same year, Essex made Docwra acting governor of Connacht and a member of the Irish privy council. In September he returned to England with Essex to seek confirmation for the governorship of Connacht. Instead, he was appointed in January 1600 commander of an expeditionary force composed of 4,200 soldiers to Lough Foyle in north-west Ulster. This was a crucial but dangerous command, requiring him to operate from an isolated base in the heart of rebel territory.
An offensive into Ulster from the south by the royal army enabled Docwra to land unopposed at Culmore on 14 May. After occupying the fort there, he proceeded to Derry on 22 May, where he built his main garrison on the site of the ruined monastery. He spent the next six months consolidating his position at Derry (also known as ‘Lough Foyle’). The need to provide shelter and a hospital for his men, and stores for his munitions and provisions, necessitated an ambitious, arduous, and time-consuming construction programme. Lacking any knowledge of the local terrain, he did not venture far from Derry. However, this meant that a number of local Irish lords who were eager to assist Docwra and provide him with that knowledge held back, lacking confidence in his ability to protect them from the rebels. The only one to meet him that summer was Sir Arthur O'Neill, and although his fort of Dunalong gave Docwra a foothold in O'Neill country, he proved a relatively feeble ally.
Moreover, Docwra's initial timidity meant that most of his men were concentrated in Derry, contributing (along with an unseasonably wet summer) to an epidemic. By late August he reported that he was down to 800 able-bodied men due to disease and desertion. Docwra earned the respect of the Irish by his conspicuous personal valour in a number of engagements, but the rebels had the upper hand. In one encounter, in late July, he was struck by a spear in the head, an injury that left him bedridden for two weeks. Sensing weakness, the rebel leader and lord of Tyrconnell Red Hugh O'Donnell (qv), closely besieged Derry during September, launching night attacks on the fort.
Meanwhile, the queen and her ministers in London were disgusted with Docwra's apparent indolence and his tolerance for the widespread embezzlement of royal funds carried out by his officers. By autumn 1600 a consensus had formed in administrative circles in both Dublin and London that Docwra was under-performing; a judgement that gave little consideration to the difficulties he faced. Despite his subsequent successes, he never dispelled the bad first impression that had formed. He suffered from a lack of powerful political patrons in London and from his association with the then disgraced Essex. The queen was horrified at the cost of her war in Ireland and held unrealistic expectations of what her commanders could achieve with the resources at their disposal. Other more well-connected generals were happy for Docwra to bear the brunt of the queen's rage at the persistence of the rebellion. A number of his subordinates, many of whom were eager for personal preferment, criticised him sharply in their dispatches. His spirited attempts to defend his conduct in a series of excessively long-winded letters only served to exasperate his superiors further.
In September the English privy council appointed Humphrey Covert as muster master for Derry, with a brief to reform the widespread corruption there. Docwra clashed angrily and often with both Covert and his successor Reynolds, eventually arresting Reynolds on trumped-up charges. They in turn were scathing about his mismanagement of his army. However, their reforms and their reports, revealing the weakened state of Docwra's forces, persuaded the privy council to dispatch a steady stream of reinforcements to Derry.
The turning point came in mid September, when the arrival of fresh provisions and then of 650 reinforcements enabled Docwra to beat off O'Donnell's attacks. Then O'Donnell's cousin Niall Garvach O'Donnell (qv) defected to the English in early October and quickly took Lifford castle with the aid of Docwra's men. Lifford was an ideal base from which to launch attacks into either Tyrone or (particularly) Tyrconnell, and O'Donnell desperately tried to retake the castle, but was forced to desist by the end of October. The rebels never besieged Derry again; and with Niall Garvach proving an able and dynamic ally with an intimate knowledge of the terrain, the military initiative had swung Docwra's way. Throughout the winter, his forces frequently raided rebel territories. By the close of 1600 he had established a line of forts heading south down the River Foyle that threatened to cut O'Donnell off from his ally, Hugh O'Neill (qv). His main priority was to plant a garrison at Ballyshannon on the coast of Tyrconnell, thereby shutting O'Donnell out of his own territory. He proceeded to achieve this by progressing gradually along the rivers Foyle and Erne. The use of longboats, both to provision his forts and to launch amphibious assaults, were central to this strategy.
During the first half of 1601 he made some incursions eastwards into O'Cahan's country, taking Aynough castle, and into Tyrone, taking the forts of Newtown and Castlederg. However, he encountered fierce resistance in these areas, and the forts taken in Tyrone fell to the rebels by treachery in September. He enjoyed more success in expanding westwards against O'Donnell and his vassal lords. In early 1601 he attempted to capitalise on O'Donnell's mishandling of a succession dispute among the O'Dohertys of the Inishowen peninsula, by entering into complex and protracted negotiations with Hugh Boy McDavitt, foster father to Cahir O'Doherty (qv), who was the young son of the previous O'Doherty lord. Some of Docwra's officers believed he was too trusting of McDavitt, but Docwra was vindicated by events. During the spring McDavitt secured custody of Cahir from O'Donnell and handed him over to Docwra, thereby bringing Inishowen into an alliance with the English. The peninsula was very fertile and was a convenient place to keep cattle. Docwra constructed a line of forts blocking the entrance to Inishowen, which repelled O'Donnell's efforts to break through in May 1601.
In July he intended marching into the heart of Tyrone to effect a junction with forces marching north from Dublin under the lord deputy, Charles Blount (qv), Lord Mountjoy. Embarrassingly, he discovered that he had insufficient match for his gunpowder and had to call off the journey. Mountjoy was both disgusted and confirmed in his low opinion of Docwra's abilities. However, Docwra made the most of this setback. Realising that O'Donnell had departed with his forces to help O'Neill resist Docwra's planned attacks, leaving the passes into Tyrconnell open, Docwra sent Niall Garvach with 500 men to take Donegal abbey, only a few miles from Ballyshannon. Although O'Donnell besieged the abbey for several months, Docwra kept his men there supplied and they repelled all assaults.
In the autumn most of the rebel forces in Ulster left the province to assist the Spanish expeditionary force at Kinsale. This enabled Docwra to devastate O'Cahan's country for the first time. His forces took Assaroe in Tyrconnell in December and finally seized Ballyshannon in March 1602. With Tyrconnell subdued, Docwra turned east and played a crucial role in mopping up resistance in central Ulster. In June he belatedly combined with Mountjoy's forces in the O'Neill heartlands at Dungannon. On 27 July he secured the submission of Donnell O'Cahan (qv), O'Neill's most important ally. However, his attempts to either capture or assassinate O'Neill failed, and the rebel leader surrendered on terms in March 1603, ending the war.
Meanwhile, Niall Garvach had demanded recognition as absolute ruler of Tyrconnell, as the price for joining the English. Docwra had made vague promises without committing himself or the government in this regard. Realising that not all his demands were going to be met, Niall became increasingly aggressive. To his credit, Docwra tried to help his former ally, but in the end lost patience and arrested him.
In May Docwra met Mountjoy in Dublin to discuss the new political dispensation in Ulster. To his dismay, Mountjoy had agreed very lenient terms with O'Neill and restored him to all of his lands. Docwra had promised rewards to his numerous Irish guides, spies, and allies, but now found that the government would not countenance this. Most seriously, O'Cahan, who had been assured of free possession of his lands, was relegated to the status of O'Neill's tenant. This decision led to a bitter quarrel with Mountjoy and undermined Docwra's credibility with the Irish. In late 1603 Docwra went to London and remained there for six months, unsuccessfully pressing his claims to be granted large tracts of formerly rebel land in Ulster. As a consolation, he was confirmed as governor of Derry for life, was appointed provost of the newly incorporated town of Derry, and received some land at Derry and 2,000 acres at Lifford. However, on returning to Derry he found that O'Neill had obtained a letter from Mountjoy guaranteeing that Docwra had no authority in O'Neill's lands.
For the next two years he concentrated on developing Derry and engaging in further recriminations with O'Neill. Feeling that his services had been poorly rewarded, he had left Derry by June 1606, selling his lands and appointing a vice-governor to rule there in his stead. His departure contributed indirectly to the O'Doherty rebellion of 1608 and earned him further official criticism. His career in ruins, he resigned as provost of Derry in 1611 and lived from 1606 to 1616 on his family lands in Berkshire. He married (c.1606/7) Anne, daughter of Francis Vaughan of Sutton upon Derwent, Yorkshire. They had three sons and two daughters. In 1614 he quarrelled with Sir Arthur Chichester (qv), lord deputy of Ireland, who had referred slightingly to Docwra's military career in Ireland. This prompted him to write accounts of both his service in Connacht in the 1580s and in Derry during 1600–03, designed to vindicate himself and to highlight the crown's appeasement of O'Neill in 1603. These narratives were not published until the 19th century.
Following Chichester's dismissal in 1616, Docwra sold some land in Berkshire, using the proceeds to buy high office in Ireland and to move to Dublin. He believed that he would be made vice-treasurer of Ireland, giving him control of royal finances there. However, he was misled; instead, the crown divided its Irish finances between a vice-treasurer who controlled all civil expenditure and a treasurer at wars who controlled all military expenditure, with Docwra receiving the latter post. To his dismay, he found that his office carried little political clout, especially in times of peace, and was not worth the money he had paid for it. Moreover, it also entailed a number of onerous obligations such as having to spend long periods in London having his accounts audited. With the government regularly failing to pay its army in Ireland, he became the obvious focus of discontent for the soldiery.
As before, his efforts to benefit from public service largely foundered. He was created baron of Culmore on 15 May 1621, but assurances of a grant of 5,000 acres of land were not honoured. Eventually, he received a small grant of land in Wicklow in 1628. Throughout his tenure as treasurer at wars, he clashed with a succession of vice-treasurers, but failed to disturb their stranglehold over Irish finances. He spent his last years unsuccessfully attempting to sell his office for £4,000, significantly lower than his purchase price. Although an able soldier and a competent bureaucrat, he was continually undone by his ineptness as a politician. He died 18 April 1631 in Dublin and was buried in Christ Church cathedral, Dublin.