Wolstenholme’s roots lay in Derbyshire, though his father settled in Middlesex after acquiring a post in the London custom house in the mid-sixteenth century. Born at Stanmore, Wolstenholme reportedly began his career working for the searcher of the custom house, and in some such capacity he supplied an account for a sale of ordnance in 1594.
With this range of experience, it was hardly surprising that Wolstenholme found himself in demand as an expert witness. During the 1614 Parliament one legislative committee was granted the power to summon him for advice on the transportation of ordnance.
Periodically, however, Wolstenholme found himself at odds with the government. In December 1619 he was placed under house arrest for opposing the creation of a new office within the custom house, while in 1622 the Privy Council summoned him for refusing to contribute to the Benevolence for the Palatinate.
While it is not clear that Wolstenholme can be regarded as one of the duke of Buckingham’s instruments in the 1624 assault on Cranfield, he certainly backed his policies during the next few years. He co-operated fully with the government in continuing to collect Tunnage and Poundage despite the 1625 Parliament’s failure to grant the duty to Charles I, and in December 1625 he entered into a new contract for the great farm of the customs on that basis. As a navy commissioner, he worked energetically to prepare the fleets which Buckingham needed for his overseas campaigns, even remaining in London during the 1625 plague outbreak in order to fulfil his duties. Later that year he also dipped into his own pocket to help fund a squadron.
Wolstenholme was one of five men returned for the two parliamentary seats at Newport on 5 Mar. 1628. He may have owed his election to his connection with Buckingham, but if so no evidence of a nomination survives. Possibly he engaged the assistance of the duke’s West Country agent, (Sir) James Bagg II*, who had worked with him on preparing the recent naval expeditions, and who probably helped to secure places for Wolstenholme’s son, John, at West Looe in 1625 and 1626. Bagg’s near kinsmen, the Estcotts, were prominent figures in the Newport district, and one of them acted as a returning officer for the borough in 1628.
The 1629 session brought further controversy for Wolstenholme. During the recess he had been involved in the seizure of merchandize belonging to John Rolle, who had refused to pay Tunnage and Poundage on the grounds that these duties had not been sanctioned by Parliament. The Commons asserted that Rolle, one of their Members, was entitled to recover his goods as both he and they were covered by parliamentary privilege, but in order for this strategy to work it was essential to prove that his property had been confiscated for the benefit of the customs farmers rather than the Crown. Ultimately Charles I declined to concede this point, and Wolstenholme proved equally unco-operative. Examined before the House on 20 Feb., he maintained that Rolle’s goods had been seized on the Crown’s behalf for non-payment of duties other than Tunnage and Poundage. Moreover, he denied having any claim on them himself, as he had at the time been operating outside his normal brief and assisting the collectors of customs inwards by royal command. His arguments infuriated the Commons, but Parliament’s dissolution shortly afterwards saved him from punishment.
Despite encroaching old age, Wolstenholme remained vigorous during his final decade, sponsoring a final search for the North-West Passage and lobbying for the revival of the Virginia Company which, ironically, he had helped to close down during an internal power-struggle in 1624. Although he offloaded some of his customs farms in 1632, he remained a leading figure in the great farm until 1638, when he bowed out in protest at government interference.
