Oldisworth was educated at Oxford, becoming a fellow of Magdalen College and receiving a master’s degree in 1614. He is not known to have enrolled at an inn of court, but by 1617, when he married Susan Poyntz, the daughter of a prominent Gray’s Inn lawyer, he was living in St. Martin-in-the-Fields, Westminster, presumably at his father’s house in St. Martin’s Lane. As a younger son Oldisworth could not expect a substantial patrimony, but his wife was joint heiress to a moderate landed estate in Essex, and this property must have provided a welcome boost to his income.
Oldisworth entered the service of the lord chamberlain, the 3rd earl of Pembroke, by December 1621, when he was entrusted by the latter with the task of organizing a Christmas masque at Court. The two men had possibly become acquainted through the Mineral and Battery Company, of which Pembroke was a governor, though Oldisworth’s father had enjoyed connections with the earl’s circle for several decades.
Oldisworth’s election for Old Sarum to four successive parliaments in the 1620s was arranged by Pembroke, who controlled the borough jointly with William Cecil*, 2nd earl of Salisbury.
the business which then I gave you but a hint of, I have enlarged it to a brief, and accompanied that (as I conceive) with weighty reasons why the House should not entertain it. When it comes to a second reading, please you to draw some of them upon it, or rather out of your better armoury, that it may not be received.
The subject of the bill referred to is unknown, and thus it is uncertain whether in this instance Oldisworth was acting in his own interests or in another’s, such as Pembroke’s.
After Pembroke’s death in April 1630, Oldisworth transferred his services to Pembroke’s brother, Philip Herbert, who succeeded as 4th earl. Employed as the earl’s secretary by 1635, he relinquished this office at about the time of his election to the Long Parliament. He initially maintained his customary low profile in the Commons, becoming actively involved in proceedings only after the outbreak of the Civil War in 1642.
