Sherley was a rogue in the strictest sense of the word. He was born into a wealthy but was forced to find his own way after his families property went into bankruptcy. He had an Oxford education, but had to take to soldiering, forgoing his education.
In 1591 he went to Normandy as one of the Earl of Essex's soldiers. While there he was knighted by the French. In 1593 he was imprisoned until he renounced his foreign title. Striving to rise in stature, he married a cousin of the earl, but soon found his wife intolerable. Seeing nothing for him to gain by staying in England, he left to seek his fortune elsewhere. Sherley used his relation to the earl to aquire funds for an expedition to capture So Thom, a Portuguese island off the coast of Africa.
In May 1596 Sherley assembled eight ships carrying about 400 soldiers. The expedition was struck by disease early in the voyage. Sherley was forced to change his course to the north. Sherley took Santiago in the Cape Verde Islands but the booty was very sparse. His force much depleted, Sherley then attacked & took Santa Marta, Colombia. In early 1597, they sacked the poor Jamaican settlement of Santiago de la Vega. Their main purpose in the attack was to replenish supplies. So far the sum total of booty for his raids was pretty sparse.
While in Jamaica, Sherley met Captains William Parker & Michael Geare. The two joined with Sherley in an attack upon Trujillo (Honduras), but were unsuccessful. Next they tried their luck in attacking Puerto Caballos, & after taking it, found it to be destitute. Geare left to seek his fortune. Sherley & Parker, decided to try to march across the Guatemala mountains to the Pacific. Once again they were daunted by the severity of the trip & chose to take their remaining men through the Strait of Magellan. By this time Sherley's men have lost faith in their captain & deserted him. With his remaining ship, Sherley went back to England & also to tremendous debts.
Toward the end of 1597, Sherley was sent to Ferrara, Italy in the company of English troops. By the time they arrived the differences between Italy & England were settled & Sherley was faced with unemployment. Sherley, once again using his relationship with the Earl of Essex, managed to raise enough money to sail to Persia. He planned to establish diplomatic relations (without the consent of the crown) with the new shah. The shah made Sherley his ambassador & enlisted him to gain allies against the Ottoman Empire. When Sherley returned to England his plan was condemned & he was forbade to return to Persia. Sherley then made his rounds from royal court to court & conned nobles out of funds.
In 1607, Sherley managed to become an agent of the Spanish. During this time he wrote to Simon Simonson & John Ward trying to sway them to make attacks upon the Ottoman Empire. Two years later, in 1609, the Spanish had Sherley assemble ships in Sicily to attack the Barbary corsairs. It was planned that Sherley would join in a Spanish attack on Tunis, but instead Sherley attacked European merchantmen & looted the Greek Islands. After Sherley's failure to support Spain's attack on Tunis, he lost all influence in the Spanish courts but stayed in Spain constantly trying to gain political stature. He died destitute in Spain circa 1637.
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