Like several other of Northampton’s MPs in this period, Baldeswell was a draper. His sparsely-documented career conformed to the pattern common among the leading townsmen in that he served as bailiff and sat in Parliament while still a young man. His service as bailiff brought him difficulties. In Michaelmas term 1417 he and his fellow bailiff, John Pirie, were sued in the Exchequer of pleas for damages of £60 by John Warwick, prior of the Carmelite friary in Coventry, and Henry Preston, both of whom claimed to have been falsely arrested and imprisoned by them. The results of these actions is not recorded. Later, when the court of King’s bench came to Northampton in Easter term 1421, the two former bailiffs found themselves punished for a lesser offence, being fined 2s. 2d. as the value of the forfeited goods of a murderer for which they had failed to account.
On Baldeswell’s election to Parliament in 1423 another of the town’s drapers, William Rushden*, was among those who offered mainprise for his appearance, and in about 1427 he himself stood surety for a chaplain, wrongfully arrested by the town bailiffs, John Makesey* and John Church II*.