Lodbroke, a weaver by trade, gained admission to the guild merchant of Reading on 5 Apr. 1443, after paying a substantial fine of 16s. 8d. and the usual sum of 3s. 4d. for the celebratory breakfast. Although the fine was halved subsequently, it is clear that he was not the son of a burgess, for such sons paid less.
Following Lodbroke’s service in the first Parliament of 1449, it would appear that his business ran into trouble. In the Hilary term of 1451 he was sued in the court of common pleas by Edward Langford*, the prominent Berkshire landowner, for a debt of £40, and it may have been in order to escape the consequences of this and other lawsuits that in the following winter he took out royal letters of protection as about to depart overseas in the retinue of the duke of Somerset, the lieutenant of Calais. Whether he did actually set sail is not known. When Langford continued his suit in the Trinity term of 1453, Lodbroke was brought to answer before the justices of assize at Grandpont on 13 July, although no jury appeared to give evidence.
At an unknown date in the mid or late 1450s Lodbroke left Reading to settle in the capital, where, no longer a weaver, he established himself as a draper or ‘broker’. Yet his removal to London did not help him out of his financial difficulties. He was outlawed by the London court of husting for failing to pay a fine to the Crown for having disowned an obligation in the huge sum of £800 made to the grocer John Plomer, although on 29 Jan. 1461, after he surrendered to the Marshalsea, he obtained a pardon. Six days later he was pardoned two further outlawries, both proclaimed in Berkshire, which had arisen from his failure to appear in the court of common pleas to answer Langford’s suit and to respond to a man from Cumnor for a debt of £20. By then he had given himself up at the Fleet prison and had finally satisfied Langford of the debt of £40 and damages amounting to £11 6s. 8d.
Lodbroke’s complicated dealings with Thomas Drakys†, an attorney from Maldon in Essex, also led to litigation. In Hilary term 1468 Drakys alleged that five years earlier Lodbroke had entered a bond with him in two marks, payable in 1467, and had also borrowed six marks from him, but had failed to pay him back. Relations between them further deteriorated a few years later, when Drakys had need of 20 marks and Lodbroke said he would provide it by acquiring from Henry Ashbourne silver plate for £14, and re-selling it for 20 marks in ready money to Drakys’ use; Lodbroke and one John Saunder would be bound to Ashbourne for payment of the £14 and Drakys would be bound to them both in a statute staple. Because of the trust he had in Lodbroke he left the plate in his possession, but only received from him £3, and the threat of legal action on the statute staple. Lodbroke and Asbourne were evidently business partners, for in 1474 they together took action against Thomas Gervase of Willingale, Essex, on an bond for £30.
Meanwhile, probably in the late 1460s, Lodbroke had been in trouble again with the civic authorities. While enduring another spell in a London prison he was visited by the sole surviving executor of John White of the Isle of Wight, who threatened to sue him on an obligation for £34 he had made 20 years earlier, unless he entered another bond in £10. The executor, a goldsmith named John Werying, promised to secure Lodbroke’s release and to return the original obligation, but failed to do so, instead taking action on both bonds. Lodbroke petitioned the chancellor for a writ of certiorare directed to the sheriffs so that the cause might be heard in Chancery.
