From the 12th century onwards, if not before, the Oudeby family enjoyed considerable influence in both Rutland and Leicestershire, and Thomas himself was the son and namesake of one of the shire knights who represented the latter county in the Parliament of 1369. Thomas Oudeby the elder owned an extensive estate, centred on the villages of Stoke Dry and Saddington, which on his death (after July 1393) passed to the subject of this biography. By then the young man had already acquired land of his own in the same area and at Hathern, where he eventually made his home.
For most of his life, however, Oudeby was preoccupied with his own territorial interests in the Midlands, largely because of the amount of litigation to which they gave rise. Between 1384 and 1409 he was involved in a series of lawsuits over property in Derbyshire and Leicestershire, most notably as a result of a protracted dispute with John Wittlebury and other members of his prolific family. He also began an action against one Thomas Petymore of Leicestershire for detinue of a box of muniments, lthough the defendant managed to avoid legal proceedings by obtaining a writ of supersedeas.
Throughout his career, Oudeby was helped by a number of valuable connexions, not least of these being his own younger brother, John, the rector of Flamstead in Hertfordshire, whose administrative and financial ability led to his appointment, in 1397, as chamberlain of the Receipt of the Exchequer, a post he was still holding when, early in 1404, he was chosen by Parliament as one of the treasurers of war who were to oversee Henry IV’s expenditure of the subsidies for defence. John and Thomas remained close to each other: in September 1403, for example, they both acted as feoffees for a third brother, Ralph, who had just acquired the manor of Hacconby in Lincolnshire; and it was to Thomas that the rich and successful cleric turned when, in March 1413, he selected the executors of his last will.
Although he was promptly replaced as sheriff, Oudeby retained his seat on the Rutland bench, and soon began to serve again on royal commissions. His former attachment to Richard II was, indeed, quickly forgotten by the ever-pragmatic Bolingbroke, and in July 1401 he received a writ of summons to attend a great council at Westminster as one of the three representatives chosen from Rutland. In the following year he and Roger Flore were approached jointly, again as leading residents of the county, for possible loans to the Crown, and it appears that his local standing had never been higher. His friendship with Flore, a leading official of the duchy of Lancaster, and retainer of York’s son, Edward, earl of Rutland, probably began at about this time: they sat together in the Parliaments of 1402 and October 1404, and we know from Flore’s will that Oudeby gave him a splendid coffer in which to store his silver plate. After more than 20 years’ involvement in local government, Oudeby finally retired from public life in the autumn of 1414, having obtained a licence from the bishop of Lincoln for the private celebration of mass in his own home, and having also attended at least one of the parliamentary elections for Leicestershire (in May 1413).
