The Wintershalls were a distinguished Surrey family, whose members played a notable part in county society from the 13th century onwards. The subject of this biography belonged to the branch which farmed estates centred on the manors of Wintershall (acquired in, or before, 1227) and Shalford, so he was thus a distant kinsman and neighbour of Thomas Wintershall, who was executed, in 1400, for his treasonous part in the earl of Kent’s rebellion. He must also have numbered among his relatives the celebrated Benedictine monk, William Wintershall of Shalford, who contributed greatly to the spiritual life of St. Albans abbey during the late 14th and early 15th centuries. Our Member’s elder brother, Thomas, does not appear to have survived their father by more than a few months, so we may assume that Wintershall had already entered his inheritance on being first made a royal commissioner at the beginning of Henry IV’s reign.
Comparatively little evidence has survived about Wintershall’s career before his first return to Parliament. In April 1399 he agreed to act as an attorney in England for Thomas Asshehurst, who was about to leave for Ireland with Richard II, although he himself had every reason to welcome the change of dynasty which brought Henry IV to the throne. It was through his loyal and efficient service to the house of Lancaster that Wintershall rose to occupy a prominent position in the south-east. Besides serving no less than four terms as sheriff and six as escheator of Surrey and Sussex, he sat on the local bench at regular intervals and spent four years collecting customs at Chichester. His administrative talents received their due reward. In 1413 he became deputy constable of Windsor castle, a post which he retained for the next 19 years if not longer. On being appointed to a royal commission of inquiry into the estates of the late earl of Arundel in October 1415, Wintershall was granted custody of some of this property (centred on Banstead in Surrey), although he had to surrender it in February 1417 as a result of litigation begun by Nicholas Carew, one of the earl’s trustees.
Less can be said on the subject of Wintershall’s personal affairs. In February 1417 a Sussex man was pardoned his outlawry for failing to appear in court when being sued by him for a debt of £10, but this appears to have been one of the very few occasions on which Wintershall went to law. He performed his own duties well and efficiently: indeed it is interesting to note that in November 1424 an assignment of £9 was made to him from the Exchequer for escorting the traitor, Sir John Mortimer, back to the Tower of London after his escape from the custody of another Surrey landowner, William Yerde. In January 1430, Wintershall was honoured with the award of a papal indult permitting him as lord of Wintershall to celebrate mass in his own chapel rather than travel to the parish church of Shalford.