Winnesley’s career fits the typical type of the minor local lawyer. His family had been resident in Leominster for at least one generation. In 1408 he secured licence for his father’s burial in the priory church, a privilege extended without charge in recognition of his father’s service to the priory.
To the advantage of his legal education, Winnesley added a modest inheritance. This is largely undocumented, but it included property at Winsley (from where his family took their name) in Hope-under-Dinmore, a few miles to the south-east of Leominster.
Nearly all the other references to Winnesley in the second decade of the century concern his practice in the central courts. In 1413 he was mainpernor when a writ of supersedeas was awarded to a Herefordshire esquire, Roger Bodenham; two years later he offered surety of the peace in the court of King’s bench for a Leominster man; and in 1417 he appeared in the same court with his kinsman, William Winnesley, to offer mainprise for a Herefordshire gentlemen pardoned for a brutal murder.
At the start of the following decade Winnesley appears as a man of greater substance. By November 1420, when he conducted the borough’s parliamentary election, he had succeeded Thomas Hevyn as the abbot of Reading’s bailiff in Leominster.
In view of his legal practice in the court of common pleas, it is surprising that Winnesley should have allowed himself, when sued for debt, to incur a minor outlawry, for which he sued out a pardon in November 1423. A month later, he entered into a bond in 200 marks to the wealthy Herefordshire knight, Sir Roland Lenthall of Hampton Court (just outside Leominster), an undertaking which led to litigation in the late 1430s.
At this date, however, the bailiff had much more important matters with which to concern himself. The most striking fact about his career is his remunerative and mysterious second marriage, which had taken place by the summer of 1426.
In April 1432 Winnesley, now very much one of the county gentry, attested the Herefordshire election, and himself accepted election for Leominster. The form of the indenture implies an awareness of the tension between his twin roles as returning officer and elected MP in that it was drawn not between the county sheriff and Winnesley but between the sheriff and the town bailiff, John Bradford. Another possible explanation for this variation in form is that Winnesley was again in office as under sheriff, on this occasion to Walter Hakluyt of Eaton, near Leominster.
Winnesley was again returned for Leominster on 4 Jan. 1442 by an indenture between himself, as the abbot’s bailiff, on the one part, and the town bailiff and the attestors on the other.
The family ended in sorry circumstances. In a petition to the chancellor, Roland’s two daughters claimed that after their mother’s death, their father, by then blind, had taken a second wife, and that, notwithstanding the entail of the family’s lands on Roland’s issue by their mother, this new wife had persuaded him to disinherit them in favour of two local lawyers, John Monnington of Westhide and John Wynne. To this end, Roland suffered a common recovery in 1473. From a legal point of view their petition is of great interest, in that the basis of their complaint was that the process of common recovery was itself an unwarrantable fraud. In this they were attempting to swim against a strong-running legal tide: the common recovery was certainly a fraud (in that the compensation it supposedly offered to the disinherited heir-in-tail was a fiction), but the fraud was a practical and useful one.
