Prepared to throw in his lot with the lollard leader, Sir JohnOldcastle, whose plans for a rising in early Jan 1414 werepromptly and efficiently quashed by the King. Sympathy for thelollards was strong in Derbyshire, and it is worth noting thatanother of Oldcastle's leading supporters, the lawyer, HenryBooth, also had estates there. Orders for Chaworth's arrest wereissued on 8 Jan, and he once again found himself a captive inthe Tower. He was at first kept in chains, but at the beginningof Feb bonds worth 1,000 marks were offered by William Babingtonand his other friends as security that he would not attempt toescape if his conditions were ameliorated. Throughout thisperiod he and his fellow captives remained under sentence ofdeath, but in May they were pardoned and allowed to go free. Itis now impossible to tell how far Sir Thomas shared Oldcastle'sheretical beliefs. His later life was given over to works ofconventional piety, most notably with regard to the endowmentand assistance of Launde priory in Leicestershire, although theevidence of his will shows him to have possessed a large numberof devotional works (some of which were in English), including`a graile (gradual) manuell and a litel portose (breviary) thewhiche the saide Sir Thomas toke with hym alway when he rode',so he may well have continued the lollard practice of placingparticular emphasis on private prayer. The inclusion of hisdistant kinsman, William Booth, Archbishop of York, among thethree supervisors of his will and his appointment, in 1423, ofthe bishops of Durham and Worcester as his trustees would,however, confirm that, in public at least, he eschewed anysuspect doctrines. Once released from prison, Sir Thomasunderstandably made every effort to re-establish himself in KingHenry's good graces; and he seized the opportunity offered in1415 by the latter's invasion of France to prove his loyalty. Heindented to serve in the royal army with a personal retinue ofeight men-at-arms and 24 archers, and was duly accorded thenecessary letters of protection.
Although he never quite managed to recover the position of trustwhich he had previously enjoyed, Sir Thomas was in a sense ableto compensate for this by making a remarkably lucrative secondmarriage. By his first wife, Nicola, he had only one child, adaughter named Elizabeth, who married John, Lord Scrope ofMasham (d.1455) before 1418, and seems to have become herfather's favourite. Whereas Nicola brought little in the way ofproperty or advancement to the Chaworths, Sir Thomas's newbride, the daughter of Sir Thomas Aylesbury, added greatly totheir territorial possessions. We do not know exactly whatIsabel received at the time of her marriage, but her father wasextremely rich, and in May 1416 he made his new son-in-law oneof his principal trustees. The latter was thus singularly wellplaced to advance his own interests when Aylesbury died, twoyears later, and promptly obtained control of the manors ofMilton Keynes in Buckinghamshire and Abinger in Surrey duringthe minority of his young brother-in-law, John. The successivedeaths within the next five years of both John and his baby soncaused a dramatic change in Chaworth's circumstances, for hiswife thus became coheir with her sister, Eleanor, of all herlate father's property. Her share comprised the manors ofAlbury, Wilstone and Tiscott in Hertfordshire, Rousham inOxfordshire, Sells Green in Wiltshire, Bradwell, Broughton andDrayton Beauchamp in Buckinghamshire, Oxhill in Warwickshire,and Dodford, Blatherwycke, Pytchley and Weston inNorthamptonshire. She also inherited various tenements inCripplegate, London. Altogether, these properties were worth abare minimum of œ93 p.a.; and although part of them remained inthe hands of Isabel's widowed mother until 1436, the improvementin Chaworth's status and finances was still remarkable. He alsokept up a wide and influential range of social connexions. InFebruary 1419 he stood bail for Sir John Pelham (an executor ofHenry IV), and a few weeks later he joined with Sir RalphShirley in offering recognizances worth 200 marks to Sir RichardStanhope. His relations with Shirley did not remain cordial forlong, since, as one of the heirs of Lord Basset of Drayton, hefound himself drawn into an alliance with Humphrey, earl ofStafford, who was determined to secure the entire Bassetinheritance for himself. Whereas Chaworth's mother had beenprepared to relinquish her title to the Staffords, Shirley clungon grimly to what was legally his, and thus met with the fullforce of Earl Humphrey's displeasure. Shirley was eventuallydriven out of the property by force majeur, claiming that hiseviction had been effected `be the procurement and instance ofSir Thomas Chaworth'.10 As we have already seen, anotherprominent member of Chaworth's circle was Sir John Zouche, whoconveyed his Yorkshire manor of Bolton-upon-Dearne to him, in1422, as a trustee, and later made him a feoffee-to-uses ofother property as well. Zouche's daughter, Elizabeth, marriedSir Nicholas Bowet, a kinsman of Henry Bowet, Archbishop ofYork, and on the latter's death, in the following year, Chaworthproceeded to exploit this connexion so that he could obtaincustody of the temporalities of the archbishopric until theconsecration of the next incumbent. He went on, some time later,to consolidate the relationship by arranging a marriage betweenhis eldest son, William, and Sir Nicholas's daughter. Chaworth'syoung ward, William Fitzwilliam of Sprotborough in Yorkshire,meanwhile proved a more than suitable husband for his youngerdaughter (another Elizabeth), to whom he was betrothed whilestill a minor. An interesting list of Chaworth's other intimatesis furnished by an enfeoffment of 1423, whereby he conveyed thebulk of his estates to a new body of trustees. As noted above,he probably chose the bishops of Durham and Worcester in orderto demonstrate his return to orthodoxy, but his appointment ofThomas, Lord Roos of Helmsley, and Ralph, Lord Cromwell,provides a clear indication of where his temporal loyalties lay.He acted for a long time as Roos's feoffee-to-uses; and in 1434,some four years after the latter's death, he was permitted tofarm the manor of Orston in Nottinghamshire during the minorityof Roos's next heir. It was, however, Chaworth's associationwith Lord Cromwell which proved of particular consequence, sincethrough it he became drawn into Cromwell's longstanding andbitter feud with Sir Henry Pierrepont (his colleague in theParliament of 1423). Having wrested the Heriz family inheritancefrom Pierrepont by highly dubious means, Cromwell secured histitle, in 1431, by conveying the property to a panel ofinfluential feoffees, including Chaworth and his friend, SirRichard Vernon. Not surprisingly, then, when violence eruptedbetween Pierrepont and his other enemies, the Foljambes,Chaworth threw his not inconsiderable weight behind theFoljambes, and as head of the second jury at the Derby sessionsof oyer and terminer, in 1434, he did everything he could tosupport their allegations. He even offered bail for RichardBrown of Repton, who stood accused of attempting to procureThomas Foljambe's acquittal; and in the following year he andCromwell capitalized upon their position as royal commissionersof inquiry in Nottinghamshire to question Pierrepont's title tothe manor of Sneinton. Later, in 1440, Sir Henry tried torecover some of his losses by suing Chaworth and Lord Cromwell'sother trustees, but pressure was brought upon him to settle outof court. Chaworth remained close to Cromwell until the latter'sdeath, for the two men acted together, on New Year's Day 1448,as witnesses to an oath made by Richard Willoughby, renouncinghis inheritance. In later life he was recruited into the serviceof Henry, duke of Warwick, who made him and one of his sonsjoint stewards of his property in Leicestershire and Rutland.
In May 1449 he and his sister-in-law (who had married SirHumphrey Stafford of Grafton) complained to the King about thedamage done by deer from the forest of Rockingham to cropsgrowing on their Northamptonshire estates, and were permitted toenclose the land in question. Sir Thomas was able to consolidatehis holdings even further as a result of the death, in about1457, of John Cressy, whose next heirs were his wife and hersister. In the event, however, he did not enjoy the profits ofthese new acquisitions for very long, since his own deathoccurred, shortly after that of his wife, on 10 Feb 1459. Thecouple were buried together at the priory of Launde, where theyhad founded a chantry some seven years before.
Although he must have been well over 80 when he died, Chaworthremained active in local government until the very end.