Searle's career as a “gentleman of fortune” was marred by frequent quarrels with Sir Thomas Modyford, royal governor of Jamaica, who usually befriended buccaneers.

Searle's first known ship was the 60-ton, 8-gun Cagway, the largest of four Spanish merchantmen captured by Sir Christopher Myngs as he returned from his raid on Santa Marta and Tolú (Colombia) in 1659.

This force of 1,300 men and a dozen vessels sailed from Port Royal (Jamaica) on 1 October 1662 and two and a half weeks later disembarked to the east of their intended target.

Constant raiding by English buccaneers had prompted repeated and vociferous protests from Madrid, delivered by the Spanish ambassador to King Charles II of England.

In turn, a letter to Governor Modyford from the king stated that “His Majesty cannot sufficiently express his dissatisfaction at the daily complaints of violence and depredation” against the Spanish by the ships of Jamaica.

and pistols.” The governor was particularly pleased that they would be serving “at the old rate of no purchase, no pay, and it will cost the King nothing considerable, some powder and mortar pieces.” Although they landed successfully, Morgan dropped dead from heat exhaustion.

[1] The good old colonel, leaping out of the boat and being a corpulent man, got a strain, and his spirit being great, he pursued overearnestly the enemy on a hot day, so that he surfeited and suddenly died.

Soon after Sir Henry Morgan’s raid on Maracaibo (Venezuela), Searle and his ship were lying at New Providence in the Bahamas when a vengeful Spanish force attacked the English settlement there.

Governor Modyford reported to Lord Arlington, England’s Secretary of State: There arrived also at Port Morant the Cagway, Captain Searle, with 70 stout men, who hearing that I was much incensed against him for that action of St. Augustine, went to Macary Bay, and there rides out of command.

Weeks passed without further orders from England and the governor wrote to Arlington again, stating that Searle was still in the custody of Jamaica's Provost Marshal, awaiting trial.

The President of Panama, Don Juan Pérez de Guzmán wrote: The English, having got possession of the Relicks of our town, found a Bark in the Fasca, although I had given order that there should be none, yet had they not complied with my command, and when they would have set it on Fire, the Enemy came fast and put it out and with it they did us great damage, for they took three more with it, and made great havock of all they found in the Islands of Taboga, Otoque, and Las Islas del Rey, taking and bringing from thence many Prisoners.

De Peralta, alarmed when his men failed to return and suspicious of the barque moored nearby, weighed anchor with some difficulty and fled into the night, being out of sight by daybreak.

Years later, Captain de Peralta was captured by the English privateer, William Dampier, in the Pacific and told the story of his narrow escape from Searle with much relish.