Wryther, who acquired a messuage in Shoreham in the summer of 1402,
As Wryther’s trading concerns expanded in the late 1420s he reached the decision to set up a business in Winchester, one of the most important centres of cloth production in the country and the location of expanding markets. A measure of the success of his enterprise is that in 1430 he paid as much as 40s. towards the parliamentary fifteenth collected in the city, a sum which suggests he was then the third wealthiest person dwelling there (two others paid 50s. each, but no-one else proffered more than 20s.).
In 1429 Wryther had paid the authorities at Winchester five marks to be exonerated from serving as a bailiff in the city.
Meanwhile, in July 1437 Mercy Carew, the wealthy widow of Nicholas Carew†, and herself the heiress of much property in Winchester, had sealed bonds promising to pay Wryther £60 in three instalments, ending in August 1440. Although the purpose of the transaction remains unclear, it evidently had something to do with the rental income of £4 p.a. which Mercy received from land at Otterbourne, for not long afterwards this came into the possession of Wryther and his wife.
The elderly Wryther was among the prominent men of Cliffe who thought it prudent to obtain royal pardons in the immediate aftermath of Cade’s rebellion, which caused serious unrest in the region. In the same year, 1450, he is recorded bringing a suit against two of the leading merchants of Salisbury, William Hore II* and Thomas Freeman*, for a debt of 20 marks, and in the Easter term of 1453 he sued Thomas White, a draper from Southampton, for the substantial sum of £84.
