by Jack Blackburn
Monday February 14 2022, 3.20pm GMT, The Times

The words “black ops” conjure visions of situation rooms, helicopters and night-vision goggles, quite a world away from gunpowder, shipwrecks and intelligence briefings delivered on horseback. Such were the tools of Elizabethan espionage.

A new book claims that Elizabeth I’s spies carried out a textbook early version of a black op, with incriminating documents suggesting they were responsible for a notorious shipwreck.

The San Juan de Sicilia, a ship that had escaped the defeat of the Spanish Armada, blew up on November 5, 1588, while taking refuge in Tobermory Bay on the Isle of Mull. This was originally blamed on the Irish but it now transpires that the sinking was caused by agents working for Sir Francis Walsingham, the great espionage chief.

Timothy Ashby discovered the link while researching Elizabethan Secret Agent, a biography of his ancestor William Ashby, who was Elizabeth I’s ambassador in Scotland. He also worked as one of Walsingham’s spies and an analysis of his letters reveals that he helped to organise the sabotage of the Spanish ship.

“I think it’s fairly clear cut,” Timothy Ashby said. “I was always fascinated by treasure hunting, so I was aware of the Tobermory galleon as one of the great shipwreck mysteries. It was quite exciting really to discover this.”

The mystery of the ship has gone into local legend and beyond. Rumours that the ship was laden with gold inspired many treasure hunters, including the 11th Duke of Argyll. His search for the ship was partly dramatised in the recent BBC drama A Very British Scandal.

The story of the mission began with Elizabeth I, who was increasingly worried about the number of Spaniards who, after their defeat in the Armada, were taking refuge in Scotland, which under James VI (later James I of England) was neutral.

“She was constantly writing to Ashby to say ‘Are you working on getting the Spanish out of Scotland?’,” the historian explains. “It was of great strategic importance to the English not to have well over 1,000 Spanish soldiers there.”

The ambassador was a protégé of Walsingham and a close confidant who Walsingham said he had “a particular love” for. He was therefore quick to dispatch an agent to the Isle of Mull after he received reports that a ship had docked there.

This was the San Juan de Sicilia, whose sails were in tatters and whose soldiers were desperately short of provisions. The crew struck a deal with the islanders. The locals were to assist them in repairs, so long as the soldiers fought for them in some local disputes.

It was paramount that the mission go undiscovered. While Scotland was politically neutral in the conflict, tensions were high there after the execution of James’s mother, Mary, Queen of Scots, only the year before.

Ashby dispatched a man called John Smollet, whose objective was to ingratiate himself with the Spaniards by furnishing them with supplies and new sails. Six weeks after he arrived, and with the Spanish off besieging a castle on the mainland on behalf of the locals, the ship blew up after someone set light to the ship’s gunpowder store.

With no clear witnesses, the culprit remained anonymous but Timothy Ashby now points to a letter from the ambassador about this incident to Walsingham. Referring to the explosion, he identifies the “man who led the train” to the gunpowder as “the man known to your honour and called Smallet [Smollet]”.

While Walsingham knew the truth, the rest of the government did not. Ashby originally told the Queen’s secretary of the state that it was the fault of the “treacherous Irish”. A year later, he corrected this to say it had simply been a tragic accident. Since then, numerous theories have abounded.

The Spanish believed it was an accident while moving the gunpowder. The privy council of Scotland decided the local chieftain had betrayed his guests. Some thought it was caused by a hostage on the ship. Others, who pointed the finger of suspicion at “the merchant Smollet”, have now been vindicated.

It is unclear how many were on board, but all those that were died save for maybe two or three on the upper deck who were blown off the ship.

For Ashby it was a small incident in an eventful life of service, diplomacy and espionage. His descendant hopes that this overlooked historical figure can be seen afresh as someone who achieved much from small beginnings.

“He came from a rather obscure, rural background,” says Ashby, who is unlikely to do a follow-up on his other antecedents. “There were no other relatives who were really as interesting.”

Link to original article in The Times