In 1600 he was sent to assist
Sir George Carew in his military campaign in
Connaught. His reputation as a soldier grew, but so did his reputation for violence: he was said to have engaged in a brawl with
Thomas Butler, 10th Earl of Ormond and
Donogh O'Brien, 4th Earl of Thomond. The supposed cause was that Christopher was over-friendly with Ormond's wife (presumably this was his third wife, Helena Barry, whom he had married in 1601). The downfall and execution of Essex did not, as might have been expected, ruin Howth's career. When
Lord Mountjoy arrived in Ireland, charged with the task of ending the Nine Years' War, Christopher accompanied him on an expedition against the O'Mores of
Laois. In October 1600 he fought at the
Battle of Moyry Pass and was wounded. He was Mountjoy's right-hand man in central Ireland during the following months, although he later complained that his services were ill-rewarded. In August 1601 he was in
Ulster; when the news came of the Spanish landing he was sent to intercept
Hugh Roe O'Donnell, but failed in the attempt. At the
Battle of Kinsale, which marked the climax of the Nine Years' War, he was entrusted with preventing the Irish and Spanish armies from joining, and was successful in his mission. He is next heard of in Dublin, and then briefly became governor of
Monaghan. On the submission of
Hugh O'Neill to Lord Mountjoy, which brought the Nine Years' War to an end, his garrison was reduced. It appears that he was accused of treasonable correspondence with O'Neill, and wrote to
Robert Cecil asking for leave to come to London to clear his name. He has quarrelled bitterly with his subordinate commander,
Laurence Esmonde, 1st Baron Esmonde, and was accused, rightly or wrongly, of having illegally hanged an English servant. Complaints about his conduct led to his summary dismissal as Governor of Monaghan. He was still said to be troubled by the downfall of Essex, and also gravely embarrassed by the pro-Catholic activities of his father, who was now openly campaigning for the repeal of the
Penal Laws. Meeting with no response, either to his demands to be allowed to clear his name or to his request for a sign of royal favour, he decided to seek employment abroad, a decision no doubt made easier by the recent break-up of his marriage to Elizabeth Wentworth. The new Lord Deputy, Sir
Arthur Chichester, was persuaded to plead on Christopher's behalf with Cecil, urging that he be given employment in Ireland, but nothing was done for him and he entered the service of
Archduke Albert in the
Spanish Netherlands. Chichester was concerned that other young nobles would follow his example, but in the event, his foreign service was cut short by his father's death in May 1607. He returned home from
Brussels, to find that he had inherited an estate severely encumbered by debt. == Flight of the Earls ==