James’s background remains obscure, although his generous bequests to the parish church of Cromer in Norfolk suggest that he may have been born there. At the time of his death he owned certain unspecified property in Norfolk, which was perhaps left to him by a member of his family. His first appearance, in May 1404, as attorney or factor to the ironmonger, Richard Marlow, confirms the existence of some early East Anglian connexions, since he was then engaged in negotiating the purchase of a stolen ship and its cargo from inhabitants of Bawdsey in Suffolk. No more is heard of him until May 1412, when he was being sued by a group of men from Rochester: two of his mainpernors were London ironmongers, and it seems likely that he had by then set up in the same business on his own account. Other charges, brought against him in the court of the mayor and aldermen of London, proved far more serious. In July 1415 he was found to have assisted the orphaned daughter of a former alderman to marry without first obtaining permission from the civic authorities. He was put in prison until his fine of £40 for deliberately flouting established custom should be paid, but afterwards the court accepted a token sum of 40s. This incident had little, if any, permanent effect on James’s career, for in the following year he was not only chosen to represent London in Parliament, but was also appointed as an attorney to recover the 10,000 marks lent by the City to Henry V on the security of the wool subsidy.
Less evidence has survived about the general state of James’s finances. In June 1417 he joined with John Reynwell in advancing £40 towards the cost of Henry V’s second expedition to France. Although the loan was to be repaid from the first wool subsidy due after February 1420, James and Reynwell had still to recover the money six years later, when a second assignment was made to them out of the subsidy of tunnage and poundage. Some of James’s business affairs were extremely complex and involved large sums of money. In February 1421, for example, Sir Humphrey Stafford II, his son, Sir Richard, and his half-brother, John Stafford, then chancellor of the diocese of Salisbury, bound themselves to pay £513 in regular instalments to James, his friend, John Burgh II, and William Babington, the chief baron of the Exchequer. Babington and James subsequently acted together as co-feoffees, but the purpose of this particular transaction is open to conjecture. Nor do we know why James and nine others (including the London merchants Nicholas Wotton and Thomas Walsingham) began a suit in the court of Chancery in March 1431 against Hamon Sutton and his associates for the recovery of the enormous sum of £923. This case, which had originally been tried before the court of the mayor of the Staple of Calais, and which clearly involved them all as staplers, dragged on until the following Michaelmas, when it was finally abandoned for lack of evidence. Both parties may then have agreed to reach a private settlement rather than continue with costly litigation. Whether or not, as one Londoner alleged in 1427, James himself was guilty of usurious and extortionate practices cannot now be proved, but he was certainly rich enough to invest in land on an impressive scale.
At the time of his death, the ironmonger owned farmland, rents and tenements in St. Olave’s parish, Southwark, Croydon in Surrey, and East Anglia. If a petition addressed to the chancellor of England many years later by Joan, the widow of John Rous II of Ipswich, is to be believed, not all this property was come by honestly. Asserting that her late husband had settled part of her jointure upon him, James apparently first refused to accept the verdict given in Joan’s favour by various independent arbitrators and then set out to ruin her through a series of vexacious and costly actions at law. He is also said to have gained a financial hold over the unfortunate woman by forcing her to enter into bonds for 100 marks, which his executors subsequently tried to enforce. Even if these allegations lacked substance, there can be little doubt that James showed great acumen when dealing in land, some of which may have come into his hands as a result of foreclosures for debt. It is now difficult to tell how much property he acquired in London, since his title was quite often shared with others. His will refers to premises in Church Lane: these comprised at least one tenement and a wharf and were confirmed to him in May 1427.
James played a full part in the government of London: besides occupying four important civic offices, he attended at least seven of the parliamentary elections held at the Guildhall between 1417 and 1432. Only once, however, in November 1425, was he chosen to arbitrate in a commercial dispute, perhaps because of his evident unwillingness to become involved in the affairs of others.