In 1437 the family of Tailboys inherited the Kyme lands and were thereby elevated to the first rank of the English gentry. On the death of his elder brother, Sir Walter, in 1441, our MP was left heir apparent to these great estates, and they duly came to him on his father’s death in April 1444.
These responsibilities did not, however, put an end to Tailboys’s criminal activities. The following year saw a spate of new offences, the most serious of which, if we can rely on the less than impartial evidence of later indictments, took place at Boston on 7 Sept. 1446 when, at the head of 80 men, he staged a riot to prevent the hearing of indictments before the Holland j.p.s.
Nevertheless, leaving such favourable notices aside, Tailboys’s immunity from prosecution was not to last much longer, and like other criminal gentry he eventually lost the position in county society to which his birth entitled him. He made his first great mistake on 14 Mar. 1448 when his servants set upon John Dymmok at Langwath, near Wragby, imprisoned him for nine hours, and forced him to enter into two obligations in 500 marks each on threat of death. Since Dymmok was a member of one of the county’s leading gentry families and a servant of Robert, Lord Willoughby of Eresby, this offence could not be ignored, and it is difficult to understand why, if Tailboys was engaged in no more than a random campaign of banditry and extortion, so inappropriate a victim should have been singled out. But, whatever the reason for the assault, its had serious consequences. On 5 May a powerful commission of oyer and terminer issued out of Chancery to inquire into the MP’s crimes. It was headed by Richard Neville, earl of Salisbury, but its issue was probably the initiative of another of its members, Ralph, Lord Cromwell, who, as the leading Lincolnshire magnate, could not allow Tailboys to go unchecked. This commission transformed an affair of merely local import into a matter of wider concern. To defend his position Tailboys exploited his court connexions to have the commission overturned and so brought the Crown into the affair as his perceived protector. On 3 June the King instructed the chancellor to repeal the commission on two grounds: first, that it had been obtained ‘by sinistre informacion’ to Tailboys’s ‘utter undoing and disheritision’; and, second, that the alleged miscreant was prepared to abide by the ruling of two or three lords of the royal council in any complaints that might be brought against him.
Such partisan and politically damaging intervention on behalf of its servants was typical of the regime of William de la Pole, duke of Suffolk, in the late 1440s, but the protection that intervention gave Tailboys was to be only partial. Indeed, he had already suffered some of the consequences of his alleged criminality. Royal protection of its esquire did not prevent his detention in the Marshalsea to find security of the peace to Dymmok, although, on 13 June, he was able to secure his release when two senior household men, Sir Robert Shotesbrooke* and Edmund Hampden*, together with Sir William Lucy* and Sir Godfrey Hilton†, stood mainpernors for his appearance in the court of King’s bench in the following quindene of Michaelmas.
This is the immediate context of the famous letter Tailboys wrote to John, Viscount Beaumont, the Lincolnshire magnate closest to the court clique.
It is fair to assume that Tailboys had appealed to the duke of Suffolk as the leading courtier, just as he had appealed to Beaumont, and that this explains why the duke troubled to come to Southwell. If, however, his intercession was in the interests of compromise, his later interventions were interpreted very differently by our MP’s local opponents, led by Cromwell. Tailboys duly failed to keep his date in King’s bench on the quindene of Michaelmas, but on the following 8 Nov. he and his sureties were pardoned of the hefty sums they should have forfeit. Explicitly, this pardon was granted because of our MP’s bond to Willoughby and his presence, on the day he should have been in King’s bench, about the King’s person; but it was later claimed that it had been obtained by Suffolk, ‘by full undue combrous suyte’ to the King and ‘for grete rewardes ... promysed and yeven’.
Further assistance came to Tailboys in April 1449, when the King wrote to Lord Welles reprimanding him for his failure to find surety of the peace to Tailboys and summoning him before the Council.
In normal circumstances, the active support of the chief minister might have been enough to save Tailboys from the consequences of his crimes; yet Suffolk’s own position was coming increasingly under threat, and so, in the autumn of 1449, Tailboys turned to a more direct method of defending himself. According to the later confession of one of his servants, he began, in September, actively plotting to have his enemy Cromwell murdered.
This was the prelude to a series of private suits. Already in the previous Michaelmas term John Dymmok had sued a bill against Tailboys for the assault of March 1448, and after the King had acceded to his detention in the Tower on 20 Jan. 1450, both Cromwell and Willoughby followed Dymmok’s example, Cromwell for the Star Chamber assault and Willoughby for the loss of Dymmok’s services. On 9 Feb. a Middlesex jury awarded Cromwell massive damages of £3,000 (which the judges reduced to £2,000), and on 27 May 1451, two Lincolnshire juries awarded Willoughby and Dymmok damages which together were scarcely less considerable.
Thereafter Tailboys’s imprisonment in Newgate continued until the Yorkists took control of government after the first battle of St. Albans. On 12 Oct. 1455, perhaps surprisingly in view of his earlier affiliations, the new regime included him under the terms of a general pardon.
One can only speculate what brought about this reversal in Tailboys’s fortunes, but it is interesting to note that the terms of the recognizance into which he entered with Cromwell’s executors indicate that the tactics employed against him may not have been entirely legitimate. He undertook not to sue such writs as attaint and maintenance against any of those who had acted as jurors between Cromwell and himself or who had, at Cromwell’s instigation, prosecuted appeals against him or indicted him of felony or trespass. This suggests not only that Cromwell had orchestrated the campaign against him but that some of the indictments had been falsely procured. Moreover, the surety of the peace Tailboys was to enter into as a condition of this recognizance specifically excluded William, nephew of the late Lord Willoughby, another indication that his enemies were not themselves blameless.
None the less, while Tailboys may have had legitimate grievances, it is hard to believe that the campaign against him was provoked by anything other than his own lawlessness. This impression is strengthened by what is known of his career after his release from prison. Although he was able to sue out a general pardon in January 1458, he was excluded from the Kesteven bench in the following November, and, strikingly, he was then included in a schedule of notorious criminals against whom the Commons in the Coventry Parliament of 1459 urged the King to take drastic action. Tailboys’s inclusion was striking in that it stood in contradiction to his political sympathies: a Commons, dominated by Lancastrian loyalists, was prepared to denounce him even though he too was a Lancastrian. They clearly considered him a criminal first and a Lancastrian second.
It was perhaps fortunate for Tailboys that open war broke out soon afterwards. His violent nature allied with his extensive northern and midland estates made him one of the principal Lancastrian commanders. He may have fought at the battle of Wakefield on 30 Dec. 1460; he was knighted at the second battle of St. Albans on the following 17 Feb. 1461; and he went on to fight at Towton. Thereafter his career mirrors that of others who remained loyal to Lancaster during the northern campaigns of 1461-4. On 26 June 1461 he was one of those who raised the deposed King’s standard at Ryton and Brancepeth in the bishopric of Durham, and soon after he fled with Queen Margaret into Scotland. Attainder and the consequent forfeiture of his estates followed as a matter of course in Edward’s IV’s first Parliament, that of November 1461. In the following July, as captain of Alnwick for the Lancastrians, he was forced to surrender this Northumbrian stronghold to (Sir) Ralph Gray II*. He added to his battle honours two years later when he fought at Hedgeley Moor in April 1464 and at Hexham in the following month.
Tailboys’s near-continuous involvement in criminal activity meant that he established few close connexions with his fellow Lincolnshire gentry. He is rarely found acting as a feoffee, although, in March 1448, he was one of those enfeoffed by Henry, Lord Scrope of Bolton in, inter alia, the manor of Bolton in Wensleydale.
Tailboys differs from other well-known criminal gentry in that he was not the loser in a dispute over land or otherwise disappointed. His motives must remain obscure. Probably he was no more than ‘a lawless and ruthless gang-leader’,
Tailboys’s unfortunate career only disadvantaged his family briefly. In the early 1460s his forfeited estates were divided between adherents of the new regime with, as the principal beneficiaries, his future capturer, Lord Ogle, who had his Northumberland lands, and Sir Thomas Burgh†, who was granted the bulk of his Lincolnshire estates.