Spies at Jamestown

The Real Story

Map of the Chesapeake BaySpain, a long-standing rival with England, began watching the new English colony in Virginia soon after the settlement was established. The Spanish kept an eye on Jamestown through an extensive spy network in London and the Caribbean. With his council for war recommending decimation of the English colony in North America, King Philip III of Spain sent a spy ship to Virginia in 1611 on the pretense of searching the coastline for a previously wrecked Spanish ship.

Ships at Jamestown SettlementA small party of men went ashore at Point Comfort, a Jamestown outpost at the mouth of the James River. Captain Diego de Molina, Ensign Marco Antonio Perez along with Francisco Lembry, the ship’s pilot, were captured, questioned and taken prisoner by the English as soon as they landed. Their ship remained offshore and a local pilot, John Clarke, was sent out to help the ship navigate into Point Comfort. Following unsuccessful negotiations, the Spanish ship sailed away with Clarke held captive. When Clarke arrived in Spain, he was interrogated several times. In his confession, Clarke described the strength of the Virginia colony, some of which he exaggerated. Based on Clarke’s testimony, the Spanish council for war recommended an expedition of up to 4,000 men to wipe out the Virginia colony. But King Philip did not consider the English colony to be dangerous or valuable at the time – it was not producing riches and wasn’t a threat to Spanish commerce. Though he kept a strong navy in the Caribbean to protect returning Spanish treasure ships, the king did not believe going to war with England over Virginia was worth breaking the peace that had been established in 1604.

Spies at JamestownSo what happened to the Spanish spies in Virginia? Marco Antonio Perez died in captivity “more from hunger than from sickness,” according to de Molina. In 1613, de Molina found a way to smuggle a letter out of Jamestown sewn into the sole of a shoe worn by “a gentleman of Venice.” In the letter, de Molina described the dismal conditions at Jamestown and encouraged Philip to wipe out the colony. The king never attempted to attack the Virginia colony and several more years went by before de Molina and Francisco Lembry were permitted to leave.

In 1616, Sir Thomas Dale took de Molina and Lembry with him to England. Lembry, who was English but had fought against England during the Spanish Armada in 1588, was hung as a traitor from the yard of the ship at first sight of the English coast. De Molina was exchanged through the Spanish Ambassador in London for John Clarke. De Molina returned to Spain, where he was made general of six ships. He was stabbed to death during a mutiny on board one of his ships.