Solving the Mystery of The Tobermory Galleon

Timothy Ashby

The story of a lost ship. Has it been found?
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In 1588 a galleon, the San Juan, mysteriously sank in Tobermory, Isle of Mull. Timothy Ashby, historian and author of a new book on Elizabethan espionage traces the history of that Spanish ship.

For centuries the sunken Spanish Armada ship known as the ‘Tobermory Galleon’ has lured treasure hunters convinced she was laden with gold. The cause of her sinking has been speculative until recently, when I was able to conclusively establish that the ship was destroyed in one of the earliest known sabotage operations of the nascent English Secret Intelligence Service.

Neither a galleon nor Spanish, the ship was part of the Armada sent by King Phillip II to invade England, depose Queen Elizabeth I and restore Roman Catholicism. The San Juan de Sicilia was a 26-gun, 800-ton carrack armed merchant vessel requisitioned from Ragusa (modern Dubrovnik) for use as a cargo carrier and troop transport. Crewed by sixty-two sailors, she carried 287 Spanish, Sicilian and Flemish soldiers.

After the Armada was dispersed by storms, the battered San Juan limped into Tobermory Bay near the Isle of Mull to make repairs. The local chieftain, Lachlan Maclean of Duart, allowed safe haven in return for the Spanish troops joining his clansman in attacks on islands held by his sworn enemies the Macdonalds. Word soon reached the new English ambassador to Scotland, William Ashby, who was a senior intelligence agent of Sir Francis Walsingham, the Queen’s spymaster and Secretary of State. The English government feared that hundreds of Spanish Armada survivors seeking refuge in Scotland would join forces with Scottish Catholic forces to invade England. Ashby was ordered directly by Queen Elizabeth to negotiate their expulsion or otherwise eliminate the Spaniards.

Ashby sent John Smollet, an agent working undercover as a Dumbarton merchant, to Mull. Smollet had a chequered history as a double agent. In 1583 he offered his espionage services to the English and secretly met in London with the Queen and Walsingham, who ‘dealt roughly with him’. Smollet was ‘neither secret nor trusty and greedy of gear [fancy clothing and accoutrements]’. Walsingham decided that, however untrustworthy the Scotsman might be, he could prove useful and was therefore ‘shown some favour and promised more’.

In 1587, Smollet was arrested for plotting assassination. His crime was covered up at the instigation of acting ambassador Robert Bowes, who reactivated Smollet as an English agent in exchange for his release. Now serving as one of Ashby’s assets, the co-opted Smollet’s mission was to ingratiate himself with the San Juan’s officers and crew by providing supplies. Smollet developed ‘great trust among the Spaniards’.

After Smollet reported that the Spanish soldiers were besieging Mingary Castle on the mainland, Ashby ordered a sabotage operation hoping to destroy them and the San Juan before it could weigh anchor for Spain. The saboteur ‘entered the ship and cast in the powder upon a piece of lint and so departed. Within a short time after the lint took fire’ and the ‘great ship’ was ‘blown in the air … most part of the men … slain’. Most of the Spanish soldiers were encamped around MacLean’s seat, Duart Castle, and nearly two hundred survived.

Scotland was a neutral country, and a cover story for the operation was required. Ashby informed Lord Burghley that the San Juan had been ‘burnt by treachery of the Irish, and almost all the men consumed by fire’. This was written to conceal his, and Walsingham’s, role in the sabotage, as he told Sir Francis that eighteen Spaniards ‘saved from the ship burnt in the Isle of Mull’ arrived in Edinburgh, adding ‘the particularities thereof I think your honour understands by the party that laid the train [the trail of gunpowder to ignite the magazine] … the man known to your honour and called Smallet [Smollet]’. Ashby spirited the saboteur into England. The cover story changed over time, possibly due to altered geo-political dynamics; a year later, the ambassador wrote to Walsingham (who knew better) and to Burghley that the San Juan had caught fire and exploded ‘by casualty’ (accident), due to ‘mischance of gunpowder’.

Subterfuge was needed because the shipwrecked Spaniards were under the protection of James, who refused to hand them over to the English. Anglo-Scottish relations were so tenuous that blame had to be officially shifted to ‘treacherous Irish’ so that, as in the execution of Mary Stuart, Elizabeth could claim innocence.

The English exerted diplomatic pressure on King James to expel Armada survivors from his kingdom, dispatching a squadron of warships to threaten Edinburgh. Finally in July 1589, watched by Ashby’s agents, 660 Spaniards embarked in four Scottish ships bound for the Low Countries. A number of Spaniards missed the boat. The latter included soldiers from the San Juan who providentially arrived in Edinburgh two days after their comrades departed.

The ships sailed south along the coast before turning east across the narrow sea. In sight of Dunkirk in the Spanish Netherlands, a large number of sails appeared rapidly closing on the lumbering Scottish coasters.

The flotilla of thirty Dutch cromsters was crewed by English allies called ‘Sea Beggars’ who had played an important role in the defeat of the Armada. The Netherlanders captured one of the Scottish ships and threw all of its crew and passengers overboard to drown. They pursued the other three ships which deliberately ran themselves ashore and broke up under heavy fire. Three hundred more Spaniards and Scots died, only a handful managing to struggle through the surf to safety ashore.

Like the sabotage of the San Juan, this attack appears to be another well-coordinated ‘Black Op’ against the Spanish with the Sea Beggars serving as proxies after being alerted by English agents. Similarly, the English were able to claim ‘clean hands’ and blame the attack on others, in this case the Dutch.

Timothy Ashby is a historian and writer, and author of Elizabethan Secret Agent: The Untold Story of William Ashby 1556-1595, is out now.