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company of English volunteers to Ferrara to assist Don Cesare d'Este, the late duke's illegitimate son, in an attempt to possess himself of the duchy to which the pope laid claim. Shirley left England with his brother Robert and some twenty-five gentlemen adventurers, and never returned. On reaching Venice, he learnt that the dispute respecting Ferrara had been settled by Don Cesare's submission to the pope. Shirley reported to Essex the posture of affairs, and, according to his own narrative, received instructions to make his way to Persia with the twofold object of persuading the Persian king to ally himself with the Christian princes of Europe against the Turks, and to promote commercial intercourse between England and the east. The enterprise was without official sanction. The English government were not consulted, and they viewed his mission with suspicion. When Shirley subsequently sought permission to return to England, it was peremptorily refused, and English ambassadors abroad were warned to repudiate his pretensions.

Shirley and his brother Robert left Venice with their twenty-five English followers on 29 May 1599. At Constantinople Shirley raised four hundred pounds from the English merchants, and at Aleppo five hundred pounds, ‘wherewith he charged Essex by bills’ (Chamberlain, Letters temp. Eliz., Camden Soc.). From Aleppo he proceeded down the Euphrates to Babylon, and, passing into Persia to Ispahan by way of Kom, met the shah Abbas the Great at Kazveen. The two favourite wives of Shah Abbas were Christians, and they procured for Shirley a very promising reception. He won, too, the regard of Aly-verd Beg, the chief of the army, and the rank of mirza, or prince, was conferred upon him. A firman was issued to him, granting for ever to all Christian merchants freedom from customs, religious liberty, and the right to trade in all parts of the shah's dominions, but no immediate advantage was taken of the concession (cf. Curzon, Persia, ii. 538). After five months' stay in the country, the shah accepted Shirley's offer to return to Europe as his envoy and invite the princes to ally themselves with Persia against the Turks. A six months' journey, two months of which were spent on the Caspian Sea, brought him and a Persian nobleman, with six or seven other attendants, to Moscow. But the tsar, Boris Godunow, treated him with contempt, and the Persian nobleman openly quarrelled with him as to their respective precedence. Early in 1600 he took ship at St. Archangel for Stettin. At Prague he was hospitably received in the autumn of 1600 by the Emperor Rudolf II, whose offers of titles of honour he declined. In April 1601 he arrived at Rome, having visited Nuremberg, Augsburg, Munich, Innsbruck, and Trent on the way. Frequent displays of zeal for Roman catholicism secured him a good reception at the Vatican. But he outstayed his welcome. His appeals for permission to revisit England were ignored, and, retiring to Venice in March 1602, he opened a correspondence with the king of Spain and his ministers.

The English government, whose foreign agents managed to intercept many of his letters, deemed his proceedings dangerous and treasonable. At the same time he was hopelessly involved in pecuniary difficulties. Early in April 1603 he was arrested by order of the Venetian signory, either as an insolvent debtor or as a conspirator against a friendly power, and he was interned ‘in a certain obscure island near unto Scio.’ On the accession of James I his appeals to the English government were considered more favourably. Owing to their representations he appears to have been released, and on 8 Feb. 1603–4 he was granted a license from the English government ‘to remain beyond the sea some time longer.’ The curious document recommended him to the consideration of ‘the princes and strangers by whom he might pass.’ In order to improve his position at home he communicated to Sir Robert Cecil, while still at Venice, details of alleged plots that were being hatched abroad against the English government, and wrote him despatches on the affairs of Persia.

In the spring of 1605 he removed to Prague, and, after some negotiation with the Emperor Rudolf II, was employed by the imperial government on a mission to Morocco. The journey seems to have been undertaken with a view to a general report on the state of the country (cf. A … discourse of Muley Hamets rising to the three Kingdomes of Moruecos, Fes, and Sus … The Adventures of Sir A. S. … in those countries, by Ro. C., London, 1609, 4to). After four months' stay at Safi, he was received at Morocco in great state, and remained there five months. He advised the king on domestic politics, and urged an expedition against the Turks in Algiers and Tunis. He advanced money for the release of some Portuguese prisoners, and on leaving the country in the autumn of 1606 he sailed with his Portuguese protégés to Lisbon, where he sought to reimburse himself for the money he had laid out on their ransom. On 7 Sept. 1606 he wrote to Lord Salisbury of his recent adventures.