Family and Life Before 1604
Robert (b. 1568) and Thomas Wintour (b. 1571–72) were sons of George Wintour of Huddington Court in Worcestershire, and his wife Jane (née Ingleby), daughter of Sir William Ingleby of Ripley Castle near Knaresborough. A sister, Dorothy, married another conspirator, John Grant. Two agnate half-siblings, John and Elizabeth, resulted from their father's marriage to Elizabeth Bourn, following Jane's death. Their paternal grandparents were Robert Wintour of Cavewell in Gloucestershire, and his wife Catherine, daughter of Sir George Throckmorton of Coughton in Warwickshire. As scions of the Throckmortons, they could therefore claim a kinship with plotters like Robert Catesby and Francis Tresham. Their maternal uncle Francis Ingleby, a Catholic priest, was hanged, drawn and quartered at York in 1586, a fact which in the opinion of historian and author Antonia Fraser, "could hardly have failed to leave a stark impression upon the Wintour family." The Wintours took their name from the Welsh Gwyn Tour (White Tower). 'Wyntour' was sometimes used in signatures, but not 'Winter' (as the brothers are commonly named).
A faithful Catholic, Robert was married to Gertrude Talbot, daughter of the recusant John Talbot of Grafton. He inherited the Tudor Huddington Court near Worcester, along with a significant fortune with which he was known to be generous. Under Robert, Huddington Court became a known refuge for priests. The proclamation for his capture, issued followed the plot's failure, described him as "a man of mean stature, and rather low than otherwise; square made, somewhat stooping; near forty years of age; his hair and beard brown; his beard not much, and his hair short." The Jesuit John Gerard wrote that he was "esteemed in his life to be one of the wisest and most resolute and sufficient gentlemen in Worcestershire". Gerard's appraisal of Thomas was just as complementary. He was apparently an intelligent, witty and educated man, who could speak Latin, Italian, Spanish and French. "He was of mean stature, but strong and comely and very valient, about thirty-three years old or somewhat more." Thomas worked as a servant to William Parker, 4th Baron Monteagle. He was educated as a lawyer, but following several years of dissipation travelled to Flanders and enrolled in the English army. He fought against Catholic Spain in the Low Countries, France and possibly against the Turks in Central Europe. However, by 1600 his views had changed; citing his belief in the injustice of fighting against the power of Catholic Spain, like his elder brother he became a passionate Catholic. Travelling as 'Mr Winter of Worcestershire', from 24 February 1601 he spent 13 days in Rome for the jubilee, and later that year and into 1602 travelled to Spain, to petition the Council on behalf of the Catholic rebels left leaderless by the execution of Robert Devereux, 2nd Earl of Essex. Father Henry Garnet, perhaps thinking that the purpose behind Thomas's visit was to gain financial support for impoverished English Catholics, sent him to Superior Father Joseph Creswell, who made the introductions to the Spanish. This trip to Spain later became the first of two visits to be dubbed by the English government as the Spanish Treason, but Thomas's timing was unfortunate, coming as it did so soon after Spain's failed attack in Ireland, and he received only vague assurances of their support. In England he met with the Spanish embassy Don Juan de Tassis, who in August 1603 landed at Dover to help negotiate an Anglo-Spanish treaty. Tassis quickly realised that any chance of a successful Catholic rebellion was unlikely, and discounted Thomas's claim that, with funding, "3,000 Catholics" would be available for the cause. After meeting with King James he wrote to Spain emphasising the need to prioritise peace with England, over the freedom of her Catholics.
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