Today I turned the pages of Drake’s Great Armada (narrated chiefly by Captain Walter Bigges), an account of Sir Francis Drake’s West‑Indian expedition of 1585‑86, published by Thomas Cates.
The narrative chronicles the fleet’s departure in September 1585, its raids on Santiago, Santo Domingo, Cartagena, and St. Augustine, Florida, and its eventual return to Plymouth in July 1586. Operating under a letter of marque, the privateers exploited the Anglo‑Spanish war, seizing abandoned vessels, engaging in ship‑to‑ship combat, and landing parties that captured “principal church stuff” before torching towns on their exit.
What struck me most was the absence of a coherent strategic plan. The chronicle reads less like a military report than a boastful recounting of daring exploits, punctuated by grim episodes of disease, viruses and plague that crippled the crew and forced the captains to abandon the venture. The estimated loot totals “three score thousand pounds” (≈ £60 000 in 1600), a sum that modern conversion places near £9 million.
Privateering, unlike outright piracy, enjoyed legal sanction and a meritocratic ladder: success could catapult a man to wealth and rank. The men themselves showed no remorse; they thanked God for the “earnings” they gathered, embodying the high‑risk, high‑reward calculus of the age.
My uncle’s oft‑repeated metaphor resurfaced in my mind: life is a sliding scale between security and freedom. The most secure place, prison, offers the least liberty. For a seventeenth‑century sailor, the prospect of a ten‑month voyage with the chance of striking it rich outweighed the peril of never returning home.
Reflecting on this, I see a parallel in my own pursuits, each endeavor demands a balance between the safety of routine and the freedom of bold, uncertain ventures. The privateers’ willingness to gamble on the unknown reminds me that progress often requires stepping beyond the comfort of the known into the realm of calculated risk.