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 expedition into the Transcaspian region, and to try to open commercial relations with Persia. He carried also letters from the queen to the tsar and to the shah, or ‘great Sophy,’ from whom he was to endeavour to obtain letters of privilege for a free trade in his dominions. Sailing from Gravesend on 14 May 1561, he reached Kholmogori on 26 July, and taking a more expeditious route overland, arrived on 20 Aug. at Moscow, where he was delayed several months. By the middle of March 1561–2 he was permitted to proceed, carrying letters of recommendation and charged with some secret commission from the tsar, referring apparently to the relations of Russia with the Circassian princes. By the middle of June he was again at Astrakhan, and in the beginning of August, after touching at Derbend, then belonging to Persia, landed at Shabran, halfway towards Baku, and went to Shemakha, the residence of Abdullah Khan, king of Shirvan, who furnished him with an escort to the shah, then at Kazvin, thirty days' journey distant. At Kazvin, however, his negotiations were entirely unsuccessful, owing to the disturbed relations between Persia and Turkey, and Jenkinson seems to have considered himself fortunate in being able to depart alive. After another visit to Abdullah Khan, from whom he obtained letters of safe-conduct and privileges for English merchants, he arrived safely at Astrakhan on 30 May 1563, and at Moscow on 20 Aug., with all his ‘goods, merchandizes, and jewels,’ brought on the tsar's account and on the company's. There he remained through the winter, sending one of his companions, Edward Clarke, overland to England with his letters, and meantime preparing a second expedition to Persia, which started the following May, under the immediate command of Thomas Alcock [q. v.], where the date of death, repeating Hakluyt's error, is given 1563>. Jenkinson then returned to Kholmogori, and on 9 July sailed for England, arriving in London 28 Sept.

On 30 May 1565 he addressed a memorial to the queen urging the probability of the existence of a north-east passage to Cathay, and offering to take charge of an expedition to attempt it. Nothing, however, came of it, but in September he was appointed to command the queen's ship Aid, with instructions to cruise on the coast of Scotland, to prevent the Earl of Bothwell landing, and to clear the sea of pirates. The Earl of Bedford, then governor of Berwick, had licensed one Wilson, a reputed pirate, to look out for and intercept Bothwell, and he lodged a bitter complaint against Jenkinson for having, in contravention of the license, made a prisoner of Wilson and sent him to England. On the other hand, the Muscovy Company, having received a new charter, petitioned the queen that Jenkinson might be sent on another mission to the tsar to counteract the influence of an Italian agent. Jenkinson arrived in Moscow on 23 Aug. 1566, and was graciously received by the tsar on 1 Sept. The negotiations, however, proved tedious, and it was not till 22 Sept. 1567 that the tsar granted the company the privileges and the monopoly of the White Sea trade at which they had aimed.

Jenkinson probably brought the charter home overland; he was certainly in London in the following January. In the summer of 1571 he was again sent to Russia to appease the tsar, who, furious at the ill-success of his overtures to Elizabeth the year before, had annulled the privileges of the company and confiscated their property. Jenkinson arrived at St. Nicholas on 26 July, to learn that the country was being devastated by pestilence, famine, and war, and that the tsar had said that if Jenkinson ventured into the country he should lose his head. He was obliged to remain at Kholmogori, and it was not till the following spring that he was allowed to proceed. On 23 March 1571–1572 he was admitted at Alexandrof to the presence of the tsar, who stated the causes of his discontent. Jenkinson attributed everything to the mismanagement of the tsar's ambassador in England, and to the misconduct of some of the company's agents left in Russia, who, he now begged, might be delivered to him to be sent home. All this the tsar promised to consider; but it was not till 13 May that he gave Jenkinson another interview, at Staritza, when, after complimenting Jenkinson, he promised to restore the company's privileges. Jenkinson returned to England in September 1572, nor did he again undertake any lengthened voyage, ‘being weary,’ he wrote, ‘and growing old.’

He had married, in January 1567–8 (, London Marriage Licenses; Visitation of Lond. 1568), Judith, daughter of John Mersh of the parish of St. Michael's, Huggen Lane, London, and of Sywell in Northamptonshire, governor of the company of merchant-adventurers and afterwards of the company trading to the Netherlands, and of his wife Alice, daughter of William Gresham and a cousin of Sir Thomas Gresham [q. v.] He was residing at this time in Aldersgate Street, doubtless engaged in business, and taking little part in public affairs. His name appears in 1576 on a commission to consider the fitting out of