Phillips, Sir Thomas (c.1560–1636), English soldier and planter, was first son of William Phillips of London, one of the queen's customers of the wool, and his wife Joane Houghton of London. William died in 1590, leaving his heir a considerable estate in London, Middlesex, and Suffolk. Despite his family's wealth, Thomas became a soldier of fortune, serving mainly in France 1578–98, for the last ten years of which he was a captain under Henry of Navarre. He also either travelled or saw military service in Italy, Spain, Portugal, and Africa. During this period of his life, he became fluent in French and Spanish. By the time he landed in Cork (November 1598), with reinforcements to aid the crown forces against the rebels, he possessed a formidable military reputation. After serving for over a year in Munster, he was stationed in the midlands for a few months in late 1600, before being sent to Carrickfergus, Co. Antrim. In July 1602 he captured the strategically important fort of Toome, on the Bann river, and was given command of the garrison there.
By the time of the rebels’ defeat in 1603 he was ideally poised to gain in terms of land. Moreover, his commander at Carrickfergus, Sir Arthur Chichester (qv), became lord deputy of Ireland in 1605 and assiduously furthered his subordinate. In June 1605 he acquired a lease of Portrush, in September 1605 he was granted Coleraine and six adjoining townlands, and in February 1606 he was leased the fort of Toome and thirty adjoining acres. Chichester also helped prevent Phillips's garrisons at Toome and Coleraine from being disbanded. In return, Phillips acted as the governor's catspaw in his private feud with Sir Randal MacDonnell (qv), the most powerful Gaelic lord in east Ulster. There were frequent outbreaks of violence between his men and MacDonnell's tenants, leading to a writ in the court of star chamber in summer 1606. He was knighted in March 1607 and was governor of Coleraine by January 1608.
He invested heavily in Coleraine, where he lived after 1603, and waived his rights to customs on the River Bann for four years to promote its growth as a market town. In 1608 the settlement boasted fortifications, thirty houses, and a mill. Prior to the outbreak of the failed O'Doherty rebellion in 1608, he arrested Sir Donnell Ballach O'Cahan (qv) for treason (February 1608), and later maintained in Coleraine at his own expense 300 British refugees from Derry. By 1609 his prodigious expenditure on his private colony had left him financially overstretched. Indeed, his arrest of O'Cahan (who does not appear to have been a party to the O'Doherty uprising) may have been motivated primarily by his desire to resolve his financial difficulties by seizing the Gaelic lord's property directly to the west of Coleraine. However, his role in O'Cahan's eventual life imprisonment earned him the enmity of O'Cahan's kin. In another ominous development, his adversary MacDonnell, formerly regarded with suspicion by the authorities, had by 1609 found official favour. Surrounded by enemies, based in a region otherwise devoid of British settlement, and facing financial ruin, Phillips desperately needed outside support.
Given both his circumstances and his family connections with the London merchant elite (his brother Francis acted as the city's financial adviser for many years) it is likely that he was the main mover behind the crown's decision in 1609 to invite London corporation to undertake the plantation of what would become Co. Londonderry. Certainly he was in London that summer in close consultation with the chief royal minister, the earl of Salisbury (his patron of longstanding), regarding the proposed Londonderry project, and in August he brought the city's agents on a tour of the region. It was agreed that he would surrender his land at Coleraine to the Londoners (doing so in April 1610) in return for 3,000 acres near Limavady and 500 acres near Toome. In return for also surrendering to the city his rights to part of the lucrative Bann fisheries, the crown granted him an annual pension of £162 in June 1611.
However, his relationship with the city collapsed in spring 1611 when he attempted in his capacity as governor of Coleraine to restrain the London corporation's agents from illegally felling trees. The Londonders retaliated by questioning his authority, by thwarting plans to establish the county jail and courthouse at Limavady, and by delaying the formal conveyance of his property at Limavady and Moyola. Although he began building at Limavady in mid 1611, he did not receive legal title to his new holdings till late 1612, and then only after an expensive and time-consuming trip to London. Due to this delay he lost eighteen months’ rent. Phillips protested bitterly at the city of London's treatment of him, but was forced to acknowledge its superior political clout. He kept a low profile for a time and focused on erecting another impressive colony at Limavady, which came to comprise a strong castle, a village of eighteen houses, and (most strikingly) an orchard and formal renaissance gardens, for which the local Irish dubbed the townland ‘the Garden of the Soul’. During the 1610s he held 13,100 acres at Limavady and 6,300 acres at Moyola.
In 1614 his military duties brought him to the island of Isla, west Scotland, where he assisted royal forces in suppressing a highland uprising. In April 1615 Rory Óg O'Cahan plotted to surprise Limavady and kill Phillips for arresting his father seven years previously. However, the conspirators were both inept and indiscreet, and Phillips moved swiftly to arrest them after being informed of their intentions. This incident was an uncomfortable reminder of his military vulnerability, based as he was in the centre of Co. Londonderry. The heavy-handedness and disdain of the Londoners might have been tolerable had they accomplished the goal that Phillips had envisaged for them, namely establishing a strong British presence in the county. However, to his alarm and fury, they neglected to spend on fortifications and flouted plantation conditions by leasing land to the native Irish. Fearful for his security in the event of an uprising he began openly criticising the Londoners for their slackness in 1617.
At first these complaints fell on deaf ears, but by 1621 the royal authorities were becoming alarmed by the uncertain progress of the Londonderry venture. During 1621–2 Phillips compiled a monumental and damning survey of the plantation as it then stood. A series of native attacks on settlers in Co. Londonderry in 1623 seemed to confirm his bleak prognosis. As a result, the crown instructed the London corporation to implement a number of reforms suggested by Phillips and appointed him overseer of the Londonderry plantation in 1624. In 1626 the crown sequestered the corporation's Londonderry revenues, directing that these were to be placed in Phillips's custody. For its part, the city resisted Phillips's supervisory role over its Irish plantation and took measures to prevent its revenues there from falling into his hands.
In 1627 the crown established a commission to inquire into the Londonderry plantation, which Phillips was to assist. His further investigations (1627–9) produced a document which he presented to the king in 1629; it purported to reveal that the city had made profits of £150,000 between 1609 and 1629. Undeniably corners were being cut, but in this instance Phillips was wildly inflating the corporation's gains. Nonetheless, this dubious evidence was used to initiate proceedings in the court of star chamber in 1630, culminating five years later in the city's conviction for failing to adhere to the plantation conditions. As a result, the London corporation was fined £70,000 and forfeited its Londonderry properties.
Phillips regarded this verdict as a personal vindication, but victory came at a price. Although he had gained quasi-official recognition for his role in attempting to reform the Londonderry plantation in 1622, he was for long poorly remunerated for his efforts. Obliged to dig into his own pockets in order to pursue his investigations, he soon exhausted his finances. He was forced to sell his land at Moyola (1622), and in 1633 he described himself as being utterly destitute: his lands were mortgaged to the hilt, he had pawned most of his belongings, he had sold his royal pension, and he was in danger of being arrested for debt. In recognition of his services, the king awarded him £5,000 on 8 November 1635, most of which went to his creditors. He died at Hammersmith, west of London, in August 1636.
He married first Dorothy, daughter of Sir George Paulet (qv) of Crondoll in Hampshire and Jane Kyne of Lewes. She died in 1612, after bearing him four sons and a daughter. His second wife was Anne Ussher, daughter of Sir William, clerk of the Irish council; they had one daughter. He was succeeded by his eldest son, Dudley. In a further testament to his conscientious promotion of British security interests in Ulster, his castle at Limavady held out while all those around it fell to the catholic rebels during the wars of the 1640s.