Hippisley’s grandfather acquired an estate in Somerset after the Dissolution of the Monasteries.
Both Hippisley’s marriages connected him with the Norton family of East Tisted, Hampshire, and at the general election of 1620 he was returned with his brother-in-law Sir Richard Norton* for Petersfield on the latter’s interest. He was named to a sub-committee to consider the abuses of informers (21 Feb. 1621); his only other appointments were to draft bills to regulate inns, the price of horse-meat, and the clerk of the market (25 Apr.), and to consider a private land bill (8 May).
Hippisley accompanied Charles and Buckingham to Spain during the summer of 1623, returning on 10 Aug. with a wildly optimistic report on the prince’s marriage negotiations.
When Buckingham became lord warden of the Cinque Ports in the autumn of 1624 he appointed Hippisley as deputy warden and lieutenant-governor of Dover Castle in place of Sir Henry Mainwaring*.
Hippisley was anxious to exploit to the full the lord warden’s interest in the general election of 1626, and blamed Buckingham’s inertia for his failure to secure the second seat at Dover for his wife’s cousin William Beecher*.
Being one of the commissioners for the sale of prize goods, Hippisley assured the Commons on 2 May that the receipts from the sale of prizes had been duly paid into the Exchequer.
Following the dissolution, in October 1626, Hippisley volunteered to victual a naval pinnace that was operating from Dover rather than send her to London to be resupplied. This arrangement proved so successful that over the next few years Hippisley provided more than £3,800 worth of victuals for the Navy, which he paid for out of the proceeds of the prize goods sold locally.
Ahead of the next general election Hippisley wrote to his patron with surprising bluntness. ‘Give me leave to tell you’, he requested on 2 Feb. 1628, ‘that you have the part of a wise and discreet man to play ... which is that you make as many burgesses as you can’. He further recommended that Buckingham’s former enemy, the 3rd earl of Pembroke, be asked not to nominate for election men like Sir Thomas Lake I* and Dr. Samuel Turner*, both of whom ‘for their own ends cares [sic] neither for the king nor commonwealth’. Again proposing Beecher for Buckingham’s nomination at Dover, Hippisley promised that ‘I will come in upon my own strength, or else I may well be missed, and you shall see I have [not] carried myself so ill in the place you have set me in, which by your leave I care not how soon I leave’.
In the Commons Hippisley again came under attack for abusing his position as lieutenant of Dover; on 29 Apr. 1628 John Pym* informed the House that a Scottish merchant, Archibald Nicolls, had complained to the Lords about the seizure of his goods. Pym proposed to allow Hippisley to testify in his own defence in the Upper House; but after some debate this was refused.
Hippisley was back in Dover by 12 Aug., when he reported to Buckingham that the pinnaces recently built for the Navy known as the Lion’s Whelps were doing wonders, adding: ‘would this had been done before the Parliament, then had the duke never been spoken on there’.
Despite petitioning for various posts at Court, and lending £1,000 to the Crown in 1631, Hippisley received no further marks of royal favour.
