Shortly before his death at the hands of a group of local men, Thomas Booth drew up a will in which he divided all the livestock and provisions on his Lancashire estates between his three sons, as well as leaving each of them £20 in cash. Henry, the youngest, must still have been a mere child, and no more is heard of him until the late 1390s, by which time he had moved to Derbyshire. It was almost certainly through marriage that he acquired the manors of Sinfin and Arleston together with holdings in the villages of Littleover, Eckington, Twyford and Normanton. He was living at Littleover when, in June 1398, he obtained a royal pardon; and two years later he sued out a fine in the court of common pleas confirming his ownership of property there. Not long afterwards, he moved to Arleston, which became his principal seat. In the summer of 1408 he and his wife, Elizabeth, bought property in Derby, but she died soon afterwards leaving him in sole possession. He remarried almost immediately, conveying the tenements in question to his own trustees. He is not known to have made any further acquisitions, so the assessment of £26 p.a. upon which he was taxed in 1436 probably held good from the early years of the century onwards.
Booth had already secured some powerful connexions by January 1395 when he was awarded royal letters of protection for a period of six months to be spent in Ireland with Thomas, duke of Gloucester. His association with one of the leading Lords Appellant of 1388 (who was murdered during the political reprisals of 1397) no doubt explains why he deemed it expedient to secure the above-mentioned pardon from Richard II, especially as he also appears to have been connected with Henry of Bolingbroke (another Appellant). When the latter landed at Ravenspur in July 1399, intent on reclaiming the inheritance which King Richard had confiscated from him, Booth was among the sizeable contingent of Derbyshire gentry who travelled to meet him. In the following November he was assigned a sum of £12 to cover his expenses as a bodyguard both then and at the Parliament which met later at Westminster. He may even have used his influence with the newly crowned Henry IV to obtain preferment for his elder brother, John, with whom he evidently maintained cordial relations. In about 1405 he offered the latter a bond in £20, perhaps as a result of dealings over the family inheritance.
Henry Booth was one of the more distinguished captives (along with another Derbyshire MP, Sir Thomas Chaworth) who were committed to the Tower of London after the failure of a coup d’état staged by the heretic, Sir John Oldcastle, and his supporters late in 1413. Several of the ringleaders were hanged immediately, while Booth and his fellows were held in custody under sentence of death. On 8 Feb. 1414, Booth’s elder brother, John, and one of his nephews joined with his father-in-law to offer securities of 1,000 marks as a guarantee that he would not attempt to escape from prison if ‘irons and other distresses’ were removed. His detention lasted for several months until the two powerful Derbyshire knights, Sir Richard Stanhope and (Sir) Roger Leche (his former client) bailed him out, probably on the condition that he should purge himself of heresy. This, however, he did not do until January 1418, perhaps because of administrative problems caused by the death of Bishop Burghill of Coventry and the subsequent absence of his successor at the Council of Constance. These events cast an interesting light on Booth’s religious and political beliefs, especially as he was further accused, in 1414, not only of receiving, supporting and maintaining a lollard priest named Walter Gilbert at his home, but also of preaching heresy himself at Littleover on various occasions. How far his views were influenced by his father-in-law, John Fynderne, is now impossible to determine, but it is worth noting that Fynderne knew Sir John Oldcastle, and, in 1418, offered securities for one of his adherents.
Meanwhile, in July 1415, Booth repaid the kindness of his relatives in standing surety for him as a prisoner by performing a similar service when they took on the lease of estates in Lancashire, seised much earlier, in 1403, from the rebel Geoffrey Bulde. A few months later, on the intervention of Parliament, he and the other executors of the influential Derbyshire knight, Sir John Dabrichecourt, obtained formal letters of pardon for any outstanding debts or fines owed by the deceased. Booth was himself returned to the House of Commons for the first time in 1420, having previously attended the Derbyshire elections of 1413 (May), 1416 (Mar.) and 1417. (He subsequently attested the returns of 1421 (Dec.), 1422 and 1426 as well.) He had strong personal reasons for seeking election to this particular Parliament, as the Lancashire branch of his family were then embroiled in a bitter dispute with Geoffrey Bulde, who was fighting to recover his confiscated property. Henry Booth’s return on this occasion (along with his brother, John, and Richard Shirburne, one of the arbitrators chosen to settle the quarrel) suggests that the Booths were making an all-out attempt to gain support for their case. Furthermore, another of the petitions considered at this time by the two houses concerned an attack launched upon Henry and his friend, William Pirton, by John Legh of Cheshire ‘ove grande poiar des gents du di Countee ... arraiez en manere de guerre’.
It was, no doubt, because of his expertise as a lawyer that Booth attracted so many clients, some of whom retained him formally through the payment of a regular fee. Ralph, Lord Cromwell, Sir Richard Vernon and Henry, Lord Grey of Codnor, each awarded him annuities: indeed, in 1434, when Grey and Vernon were indicted on a charge of distributing liveries illegally, Booth’s name was temporarily omitted from the list of jurymen serving at the sessions of oyer and terminer in Derbyshire because he, too, was involved in the case. He none the less remained active in Grey’s employment until at least 1441, the date of an allocation of expenses made to him as a councillor for ‘attending with his household servants’ upon his patron. The last clearly dated reference to Booth occurs in December 1441, when he was a party to various financial transactions concerning the Stathum family. He is said to have died five years later, and to have been succeeded by his son.