As a younger son of one of the wealthiest Lincolnshire families, John Tailboys was endowed by his father with an estate sufficient to enable him to play a role in local affairs. The form this endowment assumed was, however, far from straightforward. An inquisition taken in April 1468, nearly a year after John’s death, found that his father had granted him, in tail general and with the licence of Henry IV, the former Umfraville manor of Stallingborough near Grimsby. But these findings were false. The true story appears in an earlier inquisition of September 1467. It states that Stallingborough had been leased in 1396 by William Kyme (who, other evidence shows, had the manor in tail male by grant of Gilbert Umfraville, earl of Angus) to Sir Walter Tailboys for a term of 20 years; that Sir Walter had demised his interest to John; and that John had continued his possession beyond the term, to, it implied, the disinheritance of the leasor’s grandson, another William Kyme.
Although seemingly improperly acquired, this manor was the principal contributor to John’s income, assessed at 40 marks p.a. in 1436 and hence well beyond the expectations of most youngers sons even of families as substantial as Tailboys (although part of this income was probably drawn from fees).
Such a record was exceptional for a younger son and must have owed something to his service to his social superiors. His first master appears to have been the Lincolnshire lawyer William Lodington of Gunby, who was elevated to the bench of the common pleas in 1415. Lodington’s access to royal patronage explains the grant of 16 July 1418 to him and our MP of the 12-year keeping of the forfeited Despenser manor of Bonby, which lay not far from Stallingborough, a grant which Tailboys was obliged to surrender on the justice’s death in January 1420. Thereafter he acted as one of the feoffees for the implementation of Lodington’s will.
This connexion probably also explains Tailboys’s marriage to the half-sister of another adherent of Cromwell, the wealthy Nottinghamshire esquire, John Cockfield. This marriage had taken place by Hilary term 1429, when our MP and his wife sued for the recovery of a small Lincolnshire estate at Wainfleet and Thorpe St. Peter that they claimed as the entailed inheritance of her mother. Earlier, that inheritance had also included property in Stallingborough, and it may be that Tailboys further augmented his lands there by marriage.
As a man so intimately associated with the greatest of the Lincolnshire magnates, Tailboys was bound to be in heavy demand from his family and neighbours as an executor and feoffee. During the course of his career he figured as an executor for his mother Margaret, his namesake, John Tailboys, rector of Staveley in Derbyshire, and the Lindsey clerk of the peace Richard Duffield*, and as supervisor of the will of Sir Thomas Cumberworth*.
After his patron’s death in 1456, John maintained his place in local affairs. His nephew’s partisan support for the house of Lancaster did not prevent our MP adapting to the regime of Edward IV. Indeed, it is possible that he had a positive allegiance to the Yorkist cause. He was removed from the Lindsey bench in November 1458, only to be restored by the Yorkists two years later;