O ne of the most consequential events in the 16th century Anglo-Spanish War happened when the mighty Spanish Armada naval fleet unexpectedly failed at the hands of the English. A confluence of “bad luck, bad tactics and bad weather,” as the BBC History Magazine writes, felled the Spanish despite their initial advantage. A once-in-a-lifetime auction at Sotheby’s London offers a singular glimpse into this historic geopolitical turning point: a single lot of fouಞr papers detailing the S൲panish Armada’s attempt to invade England in 1588, ไwith three of them signed by King Philip II himself – one of the most powerful ﷺmonarchs in European history.

Upcoming Auction

Books, Manuscripts and Music from Medieval to Modern

26 June–10 July 2025 | 1:00 PM BST | London

Written on sturdy, handmade paper made from linen rags, the 16th-century Spanish Armada papers are exceptionally well-preserved. “There's something extraordinary i𓃲n not just that they survive, but that you can actually hold them,” says Gabriel Heaton, Director and Specialist of Books and Manuscripts at Sotheby’s London. “That sort of connection with a figure from hundreds of years ago is pretty extraordinary.”

The events of the Spanish Armada were a long while in the making. Spain spent years bolstering an intimidating naval fleet so it could overwhelm English ships guarding the Channel. Armed with the Pope’s blessing, the Spanish🦂 then sought to overthrow Queen Elizabeth and restore Catholicism throughout the region. The English navy was thought to have fewer resources than Spain💫, which made Philip II confident that the Spanish Armada would succeed.

These papers trace several critical moments of the formidable naval battle, including the appointment of Don Alonso Pérez de Guzmán, Seventh Duke of Medina Sidonia, as the commander of the Spanish Armada. In 🥀that same first letter, Philip instructed the Duke of Medina Sidonia – a man who lacked naval experience – to steer the fleet towards Lisbon by a certain date 🗹and to find seamen who understood how to navigate the coast near the Netherlands.

Dated the 1st of April in 1588, the second letter shows the king’s final instructions to the Duke of𝐆 Medina Sidonia for the Spanish Armada: to join forces with the Duke of Parma and his army, then collectively make their way across the English Channel. In it, Philip outlines how the English navy might retaliate, and stressed how they might strategize on rendezvous ports if the Armada was felled by bad weather. Meanwhile, a third letter features a contingency plan, or secret instructions, for the Spanish navy should their first strategy fail. These first three letters are signed by Philip II as “Yo el rey” (“I the king.”) The fourth letter in the lot illustrates the battle orders and stations for the San Martin, the flagship of the naval fleet, not long after the Armada left Lisbon; unlike the other papers, this document is signed by the Duke of Medina🅘 Sidonia himself.

Seen as a whole, the Spanish Armada documents demonstrate why Philip II was famo🍷us for his unusual attention to detail. “He always wanted to have a great deal of oversigh𝓀t of any major campaign,” says Heaton, and made a point to weigh in on more granular events “that other monarchs would probably leave to their deputies.”

Yet the papers also provide a crucial window into further understanding why the Spanish Armada ultimately failed. While the Armada was delayed and battered by storms in the le𝔍ad-up to the battle, Philip II also made a grave mistake in underestimating the English navy’s wiles – an🍸d the more robust gunnery on their ships – that also led him to placing an inexperienced man in charge, as the documents also illustrate. “They give a fascinating insight into how the Spanish expected the Armada campaign to play out,” Heaton says.

Lot

King Philip II--Spanish Armada | Instructions to the Commander of the Armada and related documents, February-June 1588

Estimate: 200,000 – 300,000 GBP

Books, Manuscripts and Music from Medieval to Modern

26 June–10 July 2025 | 1:00 PM BST | London