Wilmot’s ancestors were living in Oxfordshire by the late fifteenth century. His grandfather, Edward, flourished as a wool merchant in Witney, and by his death in 1558 he owned several Gloucestershire manors. Wilmot’s father, Edward’s second son, inherited two of these properties, along with three rectories, and settled as a gentleman at Culham, six miles south of Oxford.
Like many soldiers in Ireland, Wilmot suffered from erratic pay. By November 1600 he was owed arrears of £400, and in March 1603, when he requested £1,000 from the government, he claimed that he had received only £500 during 15 years’ commissioned service. By now his situation was desperate, as his family estates were heavily mortgaged and he lacked the money to redeem them. In 1604, he finally got permission to return to England, where he petitioned the Privy Council for relief. In May the Crown granted him a £250 annuity in lieu of his arrears, which now stood at £1,200.
Around now, Wilmot resolved to try his luck at Court. In February 1612 he leased a house in Scotland Yard, on the northern perimeter of Whitehall Palace. Thereafter, presumably with the assistance of his uncle, Arthur Wilmot, a ‘special follower’ of Viscount Rochester, he entered the royal favourite’s circle. By April 1613 he had become a close friend of Rochester’s henchman Overbury, though when the latter was consigned to the Tower shortly afterwards Wilmot managed to retain the viscount’s patronage. In the following August Rochester arranged for his Kerry governor’s salary, suspended since his departure from Ireland, to be restored and backdated, even though Wilmot was simultaneously granted a further year’s leave of absence. When the favourite, now earl of Somerset, married in December, Wilmot provided an expensive wedding present.
In the spring of 1614 Wilmot was elected to Parliament at Launceston, doubtless with Somerset’s backing, and probably through the mediation of another of the earl’s clients, Sir Robert Killigrew*, who possessed influence within the local district.
During the latter part of 1614 Wilmot secured a further re-structuring of his finances, this time exchanging his pensions and salary for a grant of lands in Ireland worth £200 p.a. Although still on close terms with Somerset in December 1614, he seems not to have suffered through the favourite’s disgrace in the following year.
Unfortunately, this tendency to confirm the status of existing landowners, which Wilmot believed was the appropriate policy for Connaught, placed him firmly at odds with those who wished to establish plantations in the province. This latter approach was strongly advocated by the new royal favourite, Buckingham, who sought to bend Wilmot to his will with a blend of threats and rewards. In 1620 the lord president was forced to accept one of Buckingham’s clients, Sir Charles Coote, as his deputy in Connaught, but this set-back was balanced in the following January by the grant to Wilmot of an Irish peerage. However, while the new viscount paid lip service to Buckingham’s authority, in practice he continued to fight his own corner. His long years of service had rendered him a leading authority on military and Irish matters. During 1621 he was included in the Council of War which debated the Palatinate crisis, and summoned as a witness by the House of Commons’ committee established to examine the abuse of monopolies in Ireland.
In 1629 Wilmot reached the pinnacle of his career in Ireland. Following the disgrace of lord deputy Falkland (Sir Henry Carey I*), with whom he had long been at odds, he was placed in command of the army. At the same time his friend viscount Loftus, the Irish lord chancellor, became joint head of the civil administration. One of Wilmot’s first tasks on his return to Dublin was to reconcile Loftus to his fellow lord justice, the earl of Cork, who represented the Falkland interest, though in the uneasy partnership which followed there is little doubt that his sympathies lay with the chancellor. On the military front, the successful billeting of troops proved a major hurdle, as it had at Plymouth. When the Dublin authorities tried to avoid this burden by pleading their charter privileges, Wilmot reacted firmly. Concerned lest other Irish towns followed this example, he demanded swift action from the government in London, warning that the king should not let his Irish subjects ‘be suffered to learn the language of English parliaments’.
By this time the king had once more found himself in need of Wilmot’s military experience, appointing him to his new Council of War as the crisis in Scotland intensified. In January 1639 he was even half-seriously proposed as governor of Newcastle-upon-Tyne, though in the event he stayed in London to help supervise the government during Charles’s absence in the north. In December 1640 Wilmot had the satisfaction of being summoned as a witness in the impeachment proceedings against Wentworth, now earl of Strafford, though he played no significant role in the subsequent trial.