BOOK REVIEW: The Great Expedition – Sir Francis Drake on the Spanish Main, 1585-86

By Angus Konstam, Osprey Publishing, Oxford, England, (2011).

Reviewed by Charles Bogart

For the past decade, Osprey Publishing has been producing high quality, well illustrated books on various military affairs. This book is part of their Raid Series and tells the story of Sir Francis Drake’s raid on Spanish possessions in the Caribbean Sea. With a force of 21 small ships and 1,800 men, Drake, in 1585, captured and plundered the cities of Santo Domingo (Dominican Republic) and Cartagena (Columbia). This raid was planned to show the military weakness of the Spanish colonial empire, from which the Spanish Crown drew the gold and silver it needed to fight its battles of conquest in Europe.

The author begins his narrative by outlining the raids to the Spanish Main by John Hawkins and Drake during the previous decade. These raids were private for profit ventures, backed by Queen Elizabeth for the political purpose of weakening Spain and providing funds for the royal court. Next the author discusses the military-political situation in Europe during the last half of the 16th century. At this time, Spain was on the path of becoming the dominant naval and land power in Europe. In order to weaken Spain, England decided to use privately financed sea power to strike at peripheral locations vital to Spain’s financial situation.

The heart of the book is the tale of Drake’s 1585-86 raid which captured the New World towns of Santo Domingo, Cartagena, and St. Augustine. A logistical debacle, brought on by sailing before all supplies had been loaded to avoid a voyage canceling order from Queen Elizabeth, would haunt the fleet throughout its voyage and cause numerous missed-opportunities. Though Santo Domingo, Cartagena, and St. Augustine were captured, little portable wealth was found within these cities. During the raid, the fleet would shrink in size as disease decimated the men. The result was that after the capture of Cartagena, Drake had too small a force to attack Havana and other nearby choice targets.

The book closes with a discussion of what the raid accomplished and did not accomplish. The raid did not capture the wealth it was expected to and was, thus, a financial disappointment for its backers. One of the mysteries of the expedition was that the amount of money distributed to its backers was 100,000 pounds less than the total Drake reported as captured. The author’s conclusion was that Drake did not pocket this extra money, but that the value of the goods captured was inflated for propaganda purposes to make the raid appear more sensational than it was. Thus while the raid raised British morale and gave the average man a belief that an Englishman was in all ways superior to a Spaniard, diplomatically and politically the raid was a failure. Instead of deterring Spain, it caused her to make England her primary enemy. Thus England reached its greatest peril in 1588 with the sailing of the Spanish Armada which had the mission of capturing England.

The book is well-written with good maps that allow one to follow the action ashore at Santo Domingo and Cartagena. There is also an excellent bibliography for those seeking greater information on this raid.

Charles H. Bogart of Frankfort, Ky, served in the Navy from 1958-1961. He recently retired as a Planning Supervisor from the Kentucky Department of Military Affairs and is now employed as a Historian by Frankfort Parks and Historical Sites.Amazon Button

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