The Siege of 1740

Contest for Empire

The Spanish Empire was the first truly global enterprise and, by sheer landmass, the largest empire in world history. During the 16th century, Spanish and Portuguese explorers circled the globe and initiated an era of extensive colonial expansion. With the discovery of the “new worlds” of Africa, Asia, and the Americas came the rapid exploitation of the natural resources of these areas to Spain’s advantage. Trade flourished across the Atlantic between Spain and the Americas, across the Pacific between East Asia and Mexico via the Philippines, and around the horn of Africa across the Indian ocean to the Spice Islands of Indonesia. For a time, Spain dominated the oceans with its experienced navy and ruled the European battlefield with its fearsome and well-trained infantry. Massive amounts of gold and silver from the Americas financed the military capability of Habsburg Spain.

Spain sought to protect its commercial monopoly in the New World by prohibiting foreign ships from entering Spanish colonial ports. No foreigner could send goods to the colonies or take gold out of Spain in payment for goods sold to Spanish merchants without having a special license. Thus, the Spaniards gained the middleman's profit on all European goods going to their colonies. Manufacturing was also forbidden in the colonies to keep the market open for imports. Under such a restrictive system, smuggling was uncontrollable and often a necessity for the colonists’ survival. As Spanish America grew, it became increasingly dependent on illegal trade with other European nations, especially England.

The War of Jenkins' Ear

In March 1738, Captain Robert Jenkins was summoned before a committee of the House of Commons, where he exhibited a severed ear, pickled in a jar, and claimed it was "cut off in April 1731 in the West Indies by Spanish coast guards who had boarded his ship, pillaged it and then set it adrift." According to Jenkins, the Spanish coast guard sloop San Antonio intercepted him near Havana and claimed he was violating the trade laws. Jenkins supposedly insulted the Spanish captain, Juan de Leon Fandino, for which Fandino used his sword to cut off one of Jenkins’ ears, declaring, "Were the King of England here and also in violation of the laws, I would do the same for him!"

Robert Jenkins, by most accounts, was a scoundrel, a smuggler, a pirate, and apparently a perjurer as well. His story was seven years old by the time he got around to telling it, and the details were undoubtedly embellished, if true at all. Never mind that some careful observers on the occasion noticed under his long wig, it appeared that both of Captain Jenkins’ ears were still attached. It made good press.

Regardless of the truth of the story, or whose ear it might have actually been, Britain seized the opportunity to pick a fight with Spain. At stake were the spoils and wealth of the Spanish Main and the Great South Sea. What started as a colonial adventure involving Spain and Britain soon grew into a major global conflict with battles in the Americas, India, Europe, and on virtually every ocean of the world.

A British spy's watercolor painting of the Castillo's entrance.
A British spy's watercolor painting of the Castillo's entrance and south face.

Events in La Florida

The English colony of Georgia was established in 1732 as a military buffer between Florida and the vaguely defined colonies of the Carolinas. The new colony infringed significantly on Spanish territorial claims. In 1735, the Spanish launched an unsuccessful surprise attack on Savannah to eliminate the threat. Governor James Oglethorpe decided, as a precaution against further Spanish attacks, to build a series of defensive forts along the Altamaha river border and raise his own regiment of soldiers. After securing his western flank from the French by treaties with friendly Native American tribes, Georgia was in a position to threaten Spanish Florida by 1738.

With the impending war, Oglethorpe incited the Creek Indians to start harassing the Spaniards by promising rewards for Spanish scalps. Border raiding and ambushes continued through 1739 up to the outskirts of St. Augustine. By then, the British had put together a plan of attack. A combined land force of Highlanders, militia, and Native allies, supported by a Royal navy squadron, moved to attack St. Augustine and wrest Florida from the Spanish.

St. Augustine’s original garrison was of three locally-raised infantry companies and an artillery detachment, numbering only about 350 men. Anticipating trouble from the English colonies, this was reinforced by three regiments from Spain, Havana, and Vera Cruz. Along with armed Natives and militiamen, military manpower levels in St. Augustine reached almost a thousand. There were also several Spanish privateers working out of St. Augustine’s harbor during the time, bringing in numerous British merchant ships as prizes and selling their cargos at auction on the town plaza. Their success provided a rare booming economy for the city and supplemented its defense. But during the winter of 1739-1740, food supplies in St. Augustine began running low, just as the British began their invasion of Florida.

A British map showing Oglethorpe's position and the bombardment of Castillo.
A British map showing Oglethorpe's position and the bombardment of Castillo.

Invasion and Siege

Oglethorpe began moving south, his Chickasaw, Uchise, and Creek scouts searching ahead, his soldiers following, and the navy covering the coastal islands, inlets, and rivers. One by one, the English began capturing the Spanish outposts, forcing the Spanish and their allies back into St. Augustine and slowly surrounding the city. The need to feed over 2500 mouths put increased pressure on the short food supplies. There was not enough food to last for long, and the Spanish governor Don Manuel de Montiano desperately sent word to Havana for supplies and assistance. Several of the messengers were killed or captured, but finally, after evading the British Navy’s patrols, the much needed help arrived in April through the Matanzas inlet.

By May, Oglethorpe had successfully encircled and besieged St. Augustine, forcing the inhabitants inside the sheltering walls of the city while he bombarded the Castillo for nearly a month. But, as one Englishman observed, the native rock "will not splinter but will give way to cannon ball as though you would stick a knife into cheese..." Coquina, the stone from which the fort was built, actually absorbed the cannon balls fired at it. Also, each night, the Spanish secretly had been repairing and covering up the damage from the day’s bombardment. While the walls of the city defended the townspeople, the heavy guns of the Castillo de San Marcos and the long-range 9-pounders of the maneuverable Spanish galleys in the harbor held the enemy at bay.

Eventually, the siege was lifted. Running low on supplies, having troubles coordinating his land and naval forces, losing a large percentage of his Highlander regiment in a battle at Fort Mosé, and threatened by a relief force coming up from Cuba, Oglethorpe retreated to Georgia, but only temporarily. There were constant border raids and several more attempts against Fort Matanzas and St. Augustine before the war drew to a close. In 1742, The Spanish attempted an invasion of Georgia but were repulsed in the Battle of Bloody Marsh, near Oglethorpe’s base at Fort Frederica. The end of the war did not bring peace, only a truce of sorts. Both colonies remained in a stalemate. It was only a matter of time before war resumed.

That next conflict would not be long in coming. Only six years from the end of the War of Jenkins’ Ear, the starting events of what would be called the French and Indian War were seen in North America. While this war is known as a predominately Anglo – French war, Spain too would enter the conflict in support of her monarch’s cousin, the King of France. The end result of this conflict was what Spain had long feared and St. Augustine had worked so hard to prevent: Florida’s loss to the British. The loss of Florida was not due to battle, but to the stroke of a pen. The Treaty of Paris that ended the war made Florida part of the new British Empire. As the Spanish Flag left La Florida, a new colonial era began.

Last updated: April 19, 2018

Park footer

Contact Info

Mailing Address:

1 South Castillo Drive
Saint Augustine, FL 32084


904 829-6506

Contact Us