Winchcombe became a wealthy landowner, spending over £4,000 on the purchase of property in the 1540s, including the manors of Thatcham and Bucklebury in 1540,[10] Farnborough (on the Berkshire Downs) in 1542,[11] and Lockinge and Ginge in 1546.
[citation needed] He was one of the Berkshire gentry while continuing as a clothier, becoming a Justice of the Peace and a Member of Parliament, representing Great Bedwyn in 1545 and Cricklade in 1547.
[13] As one of the county gentry, John Winchcombe was asked to provide Newbury men to fight in Henry VIII's armies, beginning when he was listed as one of those to be approached "…for aid against the rebels in the north" (i.e. the Pilgrimage of Grace) in 1536.
[17] He was among those present for the reception of Henry VIII's fourth wife Anne of Cleves,[18] and his personal contacts included Sir Thomas Gresham[19] and the Protector Somerset.
Although Winchcombe has in the past been credited with founding England's first factory, no documentary evidence of a weaving workshop has yet been traced.
[20] The premises consisted of timber-framed buildings ranged around courtyards, including a panelled hall and parlour, buttery, kitchen, cheesehouse, bakehouse, bolting house and brewhouse, as well as numerous "chambers" or bedrooms.
[28] A small part of this extensive home survives on the corner of Marsh Lane, complete with external carvings and mouldings.
This was the church which was rebuilt in the 1520s and 1530s, and his merchant's mark (a capital 'I’ with a lower-case sigma across the centre) appears regularly among the roof bosses in the nave.
[34] Parts of this work are loosely based on Winchcombe's life, but the narrative is expanded by imagination and plagiarism, and it is normally categorised as fiction rather than history.
Deloney's liberties with history have led to Winchcombe being frequently confused with his father of the same name (also known as John Smallwood), who died in 1520[35] and was also a Newbury clothier.
The History of Parliament (1982) associates the name with the father, but the Oxford Dictionary of National Biography (2013) notes that it "has been plausibly argued" that Deloney's work referred to the son.