Chudleigh’s father, whose surname is often spelt ‘Chidley’, gained a taste for privateering at the age of 19 when he sailed on Sir Humphrey Gilbert’s last voyage. His activities brought him into contact with Sir Walter Ralegh†, to whom he was related through an aunt, both men serving together in 1586 as knights of the shire for Devon. In 1589, inspired by the success of Thomas Cavendish† in raiding Chile and Peru, the elder Chudleigh sold up his estates, equipped a squadron of five ships and, with Ralegh’s support at Court, embarked upon a disastrous voyage, which culminated in his death from disease.
Nothing is known of Chudleigh until February 1617, when, aged about 33, he paid £350 for a half share of the Flying Joan of London, a ship of 120 tons and 14 guns which he renamed the Flying Chudleigh. The following month, despite his father’s fate, he accepted a captain’s commission in Ralegh’s intended expedition to the Orinoco in pursuit of a treasure mine rumoured to exist in Guiana (part of modern-day Venezuela). He took no part in the subsequent seizure of the Spanish settlement of St. Thomas later that year, but was instead one of those captains who remained with Ralegh at the mouth of the Orinoco to guard against a possible attack by Spanish ships. The strength of Spanish resistance subsequently led to the abandonment of the expedition, but Chudleigh appears to have retrieved something from the voyage, returning to England in about March 1618 with a cargo of tobacco and other goods. However, the complaints of the Spanish ambassador led to the impounding of his ship, and it was not until September 1618, after he had petitioned the king and provided evidence to the royal commissioners appointed to investigate the expedition, that he obtained a warrant for her release. Further difficulties arose in the following year when, after selling the ship, he proved unable to reach agreement over his accounts with Hildebrand Pruson, the sailmaker of the Navy, who owned the other half of the ship and from whom he had bought his half share. In June 1619 Pruson, who regularly cheated his naval employees, accused Chudleigh of endeavouring to swindle him. The outcome of this case is unfortunately unknown.
Whereas Ralegh went to the scaffold for heading the abortive Guiana expedition, Chudleigh, like his fellow captain, John Pennington, was given command of an armed merchantman in the fleet sent to the Mediterranean to suppress the Algerine pirates in 1620. In June 1621 he and Sir Thomas Wilsford* sank one of the corsairs’ best men-of-war and helped put their galleys to flight, and on his return to England he received a £30 reward for taking some prizes.
In August 1624 Chudleigh was appointed to command the Speedwell and given instructions to scour the Channel. In October he transported Count Mansfeld to Flushing, but on the return journey to England the count’s drunken pilot wrecked the ship.
Holland’s fleet sailed too late to assist Buckingham, and on the return to Plymouth the Bonaventure was forced ashore at Cattewater by violent storms and badly damaged. Temporarily bereft of his command, Chudleigh was added to the Council of War in February 1628. On 23 Feb. his fellow councillors appointed him and two other captains to wait upon Buckingham to offer advice on the number of ships needed to provide a constant guard of the Narrow Seas. A short while later, on 3 Mar., Chudleigh submitted a number of proposals to the Council, among which was a suggestion that he had made as early as June 1625. This was that temporary hospitals should be erected ‘in convenient places for the relief of sick and maimed soldiers and mariners’.
The day after Chudleigh presented his propositions to the Council of War he was elected Member for Lostwithiel. He undoubtedly owed his seat to his brother-in-law Sir Reginald Mohun*, then recorder of the borough. There is no evidence that he ever took his seat. That summer he was appointed captain of the Garland in the fleet commanded by Willoughby, now earl of Lindsey. He played a dominant role aboard the flagship, it being reported by one captain that, in the councils of war convened by Lindsey, ‘nothing was concluded nor anything put to votes but what Weddell and Chudleigh for sea, Willoughby and Scott for land, thought fit to be done’.
The scaling down of naval operations following the fall of La Rochelle left Chudleigh without naval employment. The Admiralty commissioners who succeeded Buckingham nominated him to serve as admiral of the Narrow Seas in May 1629, but were overruled by Charles, who, perhaps recalling Chudleigh’s tardiness in October 1627, appointed Pennington instead.
Chudleigh bought the wardship of William Lacy of Somerset in 1631 for £200,
