Roger’s father William took a leading role in the government of New Windsor in the first half of the fifteenth century, by serving as bailiff in 1412 and steward of the merchant guild (later known as mayor) for eight annual terms between 1417 and 1446. In addition he was appointed by the Crown to collect parliamentary subsidies in Berkshire in 1434 and 1440.
Sherman regularly witnessed deeds at Windsor from the late 1430s for the next two decades.
In the course of his career, Sherman was named on several occasions as a defendant in lawsuits brought in the court of common pleas. In the Michaelmas term 1439, described as a yeoman, he was sued by Peter Fettiplace* and others for breaking into their closes at New Windsor. Perhaps he had done so in his official capacity as bailiff. Similarly, albeit much more seriously, 14 years later (during his fourth Parliament), the influential courtier John Norris* sued him and William Towe* (his fellow bailiff of 1440 and companion in the Parliament of February 1449) for failing to pay him as much as 200 marks. Perhaps this substantial sum was due from Sherman and Towe in an official capacity for works at Windsor castle, or had something to do with the borough’s fee farm. Also in the Trinity term of 1453, Edmund Rede* brought a plea of debt against Sherman and two local tradesmen for a debt of £10.
Sherman clearly did not lack influence in the locality. At an unknown date a petition was sent to the chancellor from one William Archer, who alleged that the MP had begun a false action of account against him before the constable of the castle, and then, claiming he could not be contented in that court, had discontinued the action, and begun another before the mayor and bailiffs of New Windsor. Archer had twice been arrested, and feared that by ‘grete imbracyng and mayntenaunce’ Sherman would have him condemned unless the chancellor showed him good lordship.
