A merchant of some standing like his father, Pynne had attained his majority by November 1431, when he appeared in the borough court at Great Yarmouth to sue another burgess for debt.
A few years later, Robert married his first wife, Joan. In January 1436, within a year of their marriage, the couple were among the defendants in a plea of contract sued in the borough court by John Crowmere, whose widow Robert would marry after Joan’s death. Joan herself was a widow when Pynne married her, and in mid 1436 Richard Falke sued the couple in the same court over a minor debt of 12s. Falke claimed the sum from the estate of Joan’s previous husband, John Hastyng, a prominent burgess who had died during the winter of 1434-5, having appointed her one of his executors.
At the end of the same decade, Pynne was appointed one of the bailiffs of Great Yarmouth, an office in which he would serve three further terms over the following 20 years. In the later 1440s, during his second term, he and his co-bailiff, Thomas atte Fenne*, were sued in the Chancery by John Elger, John Stroude and John Westgate. Acting in their capacity as the executors of Joan Cranele, the plaintiffs accused Pynne and atte Fenne of biased conduct in the borough court. They said that when they had brought a suit for debt against Albright Yansone de la Wyke (presumably a foreigner), the bailiffs had unfairly favoured the defendant and delayed giving a judgement, thereby forestalling the recovery of the money owed to them.
A month after the opening of his son’s only known Parliament in November 1449, John Pynne drew up his will, appointing the MP one of his executors.
Very late in life, the elder John Pynne was obliged to answer a lawsuit that Thomas Niche, a merchant from London, had brought against him in the court of common pleas. In pleadings of Michaelmas term 1450, Niche alleged that John still owed him 40s. for a butt of malmsey wine that he had sold to the Yarmouth man in the City in April 1448. John responded by obtaining licence to treat with the plaintiff out of court until early in the new year, only to die in the meantime. Niche had also had dealings with Robert, whom he likewise sued in a parallel action. In pleadings of the same Michaelmas term, he claimed that Robert had failed to pay him for wine purchased – again in London – in February 1448. In this suit he sought the significantly larger sum of £7 13s., for a butt of malmsey and another of the much rarer and more expensive ‘Tyre’ wine.
A few days after making his will, John Pynne and his second wife, Alice, had appeared in the borough court to enrol two deeds. Both dated October 1445, these recorded that the couple had settled properties which had belonged to Alice’s former husband, Bartholomew Drayton, upon themselves for their lives with remainder to the MP, and Alice’s daughter, Rose. Robert subsequently married Rose, so Alice was evidently his stepmother (nothing is known about his mother, John Pynne’s previous wife). The marriage, a second match for Rose as well as for Robert, probably took place in the early 1450s. Presumably the MP’s ship, Le Rose, was named after her.
The earliest reference to Le Rose by name is from 1458,
Soon afterwards, the same Lord Roos brought actions of debt against the MP in the borough court at Colchester. Roos was just one of several plaintiffs (who also included Sir Henry Inglose*, Robert Toppes* of Norwich, Hugh atte Fenne* and Sir John Fastolf) to sue Pynne for debt there in the 1440s and 1450s, probably in most cases in connexion with business dealings.
Notwithstanding this setback, Pynne began a fourth term as a bailiff at Great Yarmouth a few months later, and he became a j.p. in the borough before this term had ended. While bailiff, he became embroiled in yet more controversy. In the spring of 1459 he was named as an accessory to murder in the court of King’s bench. The appellant, Robert Burton, accused him and several associates, including his wife Rose, of having afforded shelter and assistance to William Snelling after the latter had beaten his brother, Seman Burton, to death with a stick at Caister near Yarmouth in February 1458. Yet when the case eventually reached trial in mid 1462 a jury sitting at Norwich found Snelling not guilty, so clearing Pynne as well.
Notwithstanding Robert Burton’s appeal, the Crown appointed Pynne to a commission of inquiry in May 1460, charging him and his fellow commissioners with investigating the complaint of David Blabour, a merchant and shipowner from Aberdeen. Blabour alleged that the crews of two Yarmouth vessels had boarded and looted one of his ships, which had been driven into their port by bad weather, and the commissioners were ordered to arrest the culprits and recover the stolen merchandise.
