Stebbing lived in the port he represented in the Commons. The full extent of his property-holdings and the dates of their acquisition are obscure, but they were clearly substantial. Towards the end of his life he inhabited a house with two small adjoining gardens which he had acquired from William Notefield*, and owned another in the High Street which John Hawley* had granted to him before setting out on pilgrimage to Santiago. To these he had added a number of messuages in both Dartmouth and Southtown, a brewery with a cellar and solar, tenements and a vacant plot in ‘Pynneslane’ and at ‘Pynneslane ende’, a small building with a garden attached ‘Aboveton’, two more close together in Hardness (which he held from Cornworthy priory for an annual rent of 2 lb. of wax), and another nearby called ‘Seint Johannes hows’. In addition, he held lands further away, in Mareknolle and Totnes.
Although Stebbing had an interest in the brewing industry he was primarily a merchant, engaged by 1428 in the cross-Channel trade. In that year, in partnership with Hugh Yon* and others, he had purchased a barge called La Kateryne, which had previously come into the possession of two other Dartmouth men, John Stanbery and John Cleve. The barge was said to have been taken from Breton enemies while sailing to Bordeaux and brought to Dartmouth by its English captors. There it had been acquired by Stebbing and his associates for 45 marks. Although Stanbery and Cleve brought a suit in the court of admiralty to recover the vessel, a panel of arbitrators resolved that they should pay Stebbing and the rest their 45 marks as well as an additional £6 10s.
Stebbing’s mercantile interests were probably an important factor in his decision to set up alternative residences as far away as Southwark and in Hertfordshire.
After his return home from Westminster, Stebbing resumed his duties as customer, an office he held for nearly 19 years in all, albeit not without interruption. In other respects, however, he met with difficulties. In the late 1420s Robert Hill* accused him and Hugh Yon of forging property deeds designed to undermine Hill’s title to his manor of Shilston, and of forcibly breaking into the property and threatening his tenants. Stebbing turned out to be less culpable than Yon, for in early 1433 he was acquitted at the Exeter assizes, while Yon was convicted and condemned to pay substantial damages.
Before long Stebbing faced fresh troubles, arising from a dispute with Elizabeth Carew, Nicholas Carew and his old associate Yon over a tenement which had formerly been in the possession of John Sampson and his wife Eleanor, and in May 1438 the mayor and bailiffs of Dartmouth were instructed to proceed to Stebbing’s house and to arrest any men who were found to have taken possession of it. Two months later, the parties agreed to put their quarrel to arbitration. Yon and the Carews appointed the prominent lawyers William Hyndeston* and John More as their arbiters, whereas Stebbing relied on Henry Drewe and John Brushford*.
It is uncertain to what extent Stebbing owed his return to the Commons in 1442, after an absence of almost ten years, to Brushford, who as mayor presided over the elections. The years between 1439 and 1442 had seen repeated military expeditions to France set out from south-western England, and on several occasions he had been charged with the organization of shipping and the victualling and payment of the masters and mariners of the ships hired and impressed for this purpose.
Stebbing’s renewed mayoralty provided him with a welcome opportunity to repay Brushford for the service he had rendered him in securing his election the previous year, albeit at the cost of some personal vexation in the law courts. In 1441 the owner and master of a barge called La Marie of St. Mâlo had complained to the Crown that La Marie had been unlawfully taken at sea by two balingers from Falmouth, and her cargo of 43 tuns of white wine sold to various individuals. A commission of inquiry had ascertained the names of the buyers, and restitution had been ordered. Fourteen tuns of the wine had been purchased by Michael Mulner, a Dartmouth merchant who died shortly afterwards, and Brushford, then mayor of the town, had received silver plate to the value of £10 from his widow and executrix. Yet, this done, Brushford had failed to make a return to the writ or to make restitution to the ship’s master, Peter Stephan, who therefore sued out a writ against the mayor in June 1444. In the interim, Stebbing had replaced Brushford as mayor and it thus fell to him to execute the writ against his friend. This he was clearly reluctant to do, and he made a formal return to the effect that he had been unable to find Brushford within his bailiwick. Stephan now turned on Stebbing, charged him with making a false return, sued him for the costs of the suit against Brushford, and even had him arrested by a royal sergeant-at-arms. He not only claimed the expense of having four writs issued twice over, but also the wages of two mounted men dispatched to Dartmouth with the documents, the cost of legal counsel and, to add insult to injury, even a payment to the sergeant-at-arms.
In spite of a violent clash in April 1444 with the lawyer John More of Collumpton, who claimed that Stebbing, Brushford and several other prominent members of Dartmouth’s merchant community had assaulted him at Kingswear and Dartmouth, killed his horses and robbed him of a purse, Stebbing continued as customer until June 1447 and throughout the decade was periodically appointed to royal commissions.
It is tempting to connect Stebbing’s final dismissal as customer in March 1455 with the appointment as treasurer of James Butler, earl of Wiltshire, but there is no definite evidence to confirm such a hypothesis. It is equally possible that he had committed some unconnected misdemeanour, for in January 1456 he sued out a fresh pardon.
Despite his heavy administrative workload, Stebbing occasionally attested deeds or acted as a feoffee for his neighbours,
During his retirement Stebbing acted more frequently as a witness to the deeds and wills of his neighbours and as a feoffee of their lands,
