The family background of this Thomas Winslow is obscure. After he had established himself as a prosperous draper in London he made his home in Essex, so it is tempting to speculate that the choice of this county reflects a wish to return to his roots. He may, therefore, have been related to William Winslow (1388-1415),
Thomas followed the lead of another putative kinsman, John Winslow (d.c.1426), by learning the drapers’ craft.
In his youth Winslow had become known to William Cromer† (d.1434), the wealthy London draper, and formed a friendship with his son and heir, another William Cromer*, who sat as a knight of the shire for Kent in 1447 and 1449. Like his powerful father-in-law James Fiennes*, Lord Saye and Sele, the treasurer of England, Cromer was put to death by the followers of the rebel Jack Cade early in July 1450. The ecclesiastical authorities appointed Winslow along with William Fiennes, the new Lord Saye, as administrators of his estate, and as a consequence Winslow became engaged in prolonged lawsuits with Cromer’s stepbrother Robert Poynings*. In the summer of 1451 Poynings accused Winslow of the theft of household goods worth £40 from Tunstall in Kent, but Winslow contended that these were Cromer’s goods, which he had in his keeping by the archbishop of Canterbury’s commission,
Winslow was asked to take on positions of trust for others besides the late William Cromer. In May 1451 his brother Richard enfeoffed him of his lands in Lincolnshire and Nottinghamshire, naming him in the distinguished company of Lords Cromwell and Abergavenny,
Winslow took out another pardon on 1 Feb. 1458, specifically as a draper of London, administrator of the goods of William Cromer, and former customs’ collector.
Meanwhile, Winslow had become an important member of the corporation of London. In June 1460 he was among the group of citizens sent by the mayor and aldermen to persuade the Yorkist earls marching through Kent to keep their army out of the city, and in the following October he served on the committee appointed by the common council to decide how best to promote the interests of the City in the Parliament summoned after the earls’ victory at Northampton.
During the 1450s and 1460s the prosperous Winslow sought to establish himself as a landowner beyond the city walls, looking not only to the nearby counties of Essex, Middlesex and Hertfordshire, but also further away to Sussex. In 1458 he began the process of purchasing the manor of Brundish in Moreton, Essex, with 1,000 acres of marshland in Fobbing and Vaunge, and having successfully defeated the claim of Thomas Brocket* (d.1477) to hold it in right of his wife, he died in possession of the manor.
Winslow also ran into trouble through his dealings with the prominent lawyer Thomas Hoo II*, whose complex and devious machinations caused frustration and financial loss to many. In Winslow’s case his dispute with Hoo arose over the sale of the Sussex manor of Moorhall in Ninfield, which had come into his possession by grant of William, Lord Saye. To purchase the manor from Winslow, in 1459 Hoo and his friend Nicholas Hussey sealed bonds for the payment of £400, the lawyer alone following this in December 1464 with two more obligations, each in £100. Yet even by the time of the Readeption Parliament of 1470-1, Hoo had still failed to honour his commitment; he was then bound over to pay Winslow £100 within six months of the dissolution. Winslow brought a bill in Chancery in the following autumn, claiming that Hoo had inveigled his way out of paying anything at all for the manor. He said that ‘ymagenyng and entendyng fraudelently to disceyve him’, the lawyer had persuaded him to show his evidences, and having done a valuation of the manor sued an assize against him at which Hoo obtained judgement to recover Moorhall with damages of £37. Hoo responded that, on the contrary, Winslow knew full well that he had ‘come bot lightly and by a faynt title’ to the manor, that the estate he had in it was ‘of non effect in the lawe’, and that he had intended to defraud Hoo by selling him a manor to which his title was not sound. Whatever the truth of the matter, Winslow gave up his vain pursuit of Hoo in the King’s bench in 1472, and Hoo contrived to retain the property.
Winslow died on 17 May 1481. His heirs were his two surviving daughters, Margaret, wife of William Nynge, and Elizabeth, wife of William Haukyns, aged 32 and 31 respectively.
