Anthony Shirley

Sir Anthony Shirley (1565 – 1633/1635/1638) also spelled ''Sherley'', was an English adventurer, soldier, diplomat, and political theorist who became a prominent figure in early modern European and Middle Eastern affairs.

Initially rising to prominence through military service under the Earl of Essex, he later led a failed privateering expedition and subsequently entered the service of Shah Abbas of Safavid Iran, becoming one of the first Englishmen to hold an official diplomatic role in Safavid Iran. Over the following decades, Shirley operated as a freelance envoy, spy, and political adviser across Europe and North Africa, offering his services to multiple courts, including the Habsburgs and the Spanish crown, often simultaneously. Though never formally trusted by the English government, he remained in contact with Robert Cecil and other high officials while maintaining parallel allegiances abroad.

A convert to Catholicism, Shirley styled himself “Count of the East” () and ended his life in Spain, where he authored ''Peso Político de todo el mundo'', an expansive geopolitical treatise assessing the relative strength of global powers. His career, marked by opportunism, shifting loyalties, and diplomatic ambition, reflected the fluid allegiances and imperial rivalries of the early 17th century.

Early years

Anthony Shirley was the second son of Sir Thomas Shirley of Wiston, Sussex, and Anne Kempe, the daughter of Sir Thomas Kempe (d. 7 March 1591) of Olantigh in Wye, Kent. He had an elder brother, Sir Thomas Shirley, and a younger brother, Sir Robert Shirley, and six sisters who survived infancy. At the age of 16, he matriculated as a bachelor at Hart Hall, Oxford. In 1581, he was admitted to All Souls College, Oxford, to pursue a master's degree. Following his university education, he entered the Inns of Court in London, where he gained recognition within aristocratic circles. During this period, he became acquainted with Robert Devereux, 2nd Earl of Essex, a prominent courtier and favourite of Queen Elizabeth I.

In service of England

Military career

His military apprenticeship began in the Low Countries around 1585-1587, serving with the English forces under notable commanders such as Robert Dudley, Earl of Leicester, during the Dutch Revolt against Spain. He was first posted to port of Brielle but gained recognition for his role in the skirmish outside Zutphen in 1586.

Shirley also claimed to have undertaken a covert diplomatic mission in late 1586 or early 1587 on behalf of Robert Dudley, Earl of Leicester. According to Shirley, Leicester tasked him with delivering two forged letters to Alexander Farnese, Duke of Parma—one purportedly from Mary, Queen of Scots, proposing marriage and a joint claim to the English throne, and the other allegedly from Leicester supporting the plan. Shirley asserted that his delivery of the letters to Parma in Bruges influenced the Spanish commander’s hesitation to march north to support the Armada in 1588. However, there is no contemporary corroboration for this claim, and historians have questioned both its plausibility and timing, particularly in light of Mary’s execution in February 1587.

Following Leicester’s withdrawal from the Netherlands and his death in 1588, Shirley served in the Anglo-French campaign to support Henry IV of France against the Spanish-backed Catholic League. Under the command of Lord Willoughby, he participated in the 1589 expedition, though specific details of his actions remain unclear. Shirley further went to Northern France in 1591, where he held a senior command under Sir John Norris. During the Battle of Château-Laudran, Shirley led a cavalry charge against a force of 500 Spanish horse and 6,000 foot soldiers, reportedly killing a Spanish captain and playing a decisive role in the English response. He also repelled a Spanish counter-attack with only fifteen horsemen, during which his horse was shot from under him.

He was soon granted the rank of colonel by the Earl, took command of 4,000 soldiers. After two years of military service, including participation in the unsuccessful siege of Rouen, in 1593, he was awarded the Order of St Michael by Henry IV of France, acting on the Earl’s recommendation. Queen Elizabeth, concerned that the ceremonial oath might have bound him to a Catholic monarch, instructed John Puckering, Speaker of the House of Commons, and Robert Sackville, a university associate of Anthony and fellow member of the Inns of Court, to investigate Shirley. He was interrogated regarding his allegiance to Henry IV, which he denied, and was instructed to renounce the knighthood. He refused, stating through his interrogators that the matter concerned his honour, which he valued above life itself. On 12 March 1594, he was found guilty during trial and, as punishment, was bound to serve there as a prisoner of the Fleet, but was shortly afterwards released after a second trial acquitted him. A compromise was eventually reached: the insignia of the order was returned to France, but Sherley retained the title of “Sir Anthony,” which continued to appear in official records. He was released and resumed his position as colonel of a regiment in Brittany, where he served until 1595.

Around this period, Sherley secretly married Frances Vernon, a cousin of the Earl of Essex. The union strengthened Shirley’s ties to the Devereux family and solidified his place within Essex’s network of influence. Frances’s sister, Elizabeth Vernon, was later married to the Earl of Southampton, a close ally of Essex. The marriage drew further ire from Queen Elizabeth, who barred Shirley from court. He and Frances settled at Englefield, Berkshire, a property purchased from Essex. In a letter to Robert Cecil, Shirley lamented his isolation from court favour. Cecil suspected the marriage had been arranged by Sherley’s father, Sir Thomas, who refuted the claim, stating the match was concluded independently by his son while abroad.

As privateer

In 1595, with backing from his father, he launched a campaign targeting Spanish and Portuguese holdings. The original plan was to seize the island of São Tomé, a Portuguese sugar depot off the West African coast. Sir Thomas purchased nine ships and raised 1,500 men for the project. The financial and administrative burdens of this enterprise were considerable, especially as Sir Thomas’s official position was becoming increasingly precarious. To legitimise the expedition, Shirley sought to attach his forces to the forthcoming Anglo-Spanish campaign led by the Earl of Essex and Lord Admiral Charles Howard. Essex secured for him a sub-commission under the broader authority of the Cádiz campaign, allowing Shirley to raise troops and equip ships under Crown sanction. The document named Shirley as commander of all forces funded by himself and his father. Having completed his preparations, Anthony set sail from Southampton on 23 April 1596, with nine ships and one galley. However, this arrangement backfired: upon mustering at Plymouth, Shirley was compelled to surrender four ships and 500 soldiers to the main fleet, compromising his own operational capacity.

Undeterred, Shirley departed in May 1596. The main source for the voyage is an anonymous account in ''Hakluyt’s Voyages'', highly flattering and often questionable. The squadron sailed along the Iberian and West African coasts with little success. Shirley fell seriously ill off Cape Verde, reportedly delivering a farewell speech appointing a successor. Though he recovered, his remaining captains—save for those aboard the ''Beavis'', his own vessel—ultimately deserted and returned to England.

Abandoning the São Tomé plan due to illness and unfavourable geography, Shirley redirected his expedition to the Cape Verde Islands. At Praia

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