The War of Jenkins’ Ear (1739-1748) was but a single episode in the prolonged series of imperial conflicts between England and Spain in the 18th century. In the summer of 1740, the conflict came to Florida.
James Oglethorpe, English military commander and founder of the Georgia colony, led the expedition against St. Augustine. In January 1740, Oglethorpe presented his plan for a swift victory before the South Carolina General Assembly. He envisioned a decisive surprise attack led by English soldiers and militia, aided by Creek and Cherokee warriors.
Surprise proved nearly impossible for the English invaders. Leading up to the advance of the main force, England’s Native American allies–principally Creek and Euchee (also Yuchi) warriors–periodically raided Spanish settlements north of St. Augustine. An incident on Amelia Island in late 1739 also alerted the Spaniards to the likelihood of an attack.
By the time Oglethorpe’s army reached the south bank of the St. Johns River on May 9, 1740, the Spanish were certainly aware of their intentions. On May 12, Oglethorpe took Fort Diego, located 20 miles north of St. Augustine near the head of the Tolomato River. Four days later he advanced on St. Augustine, but pulled back to Fort Diego on May 18. At this point, several commanders expressed dissatisfaction with Oglethorpe’s tactics. Some questioned why he did not immediately besiege the town as Colonel James Moore had done with great success four decades earlier.
During the ensuing month, Oglethorpe repeatedly marched his troops within sight of the city without launching a full assault. Regular soldiers, militia, and Indian auxiliaries again lodged complaints about the incessant and seemingly pointless marching. A group of Creeks even threatened to abandon the field, and apparently some did. Oglethorpe also divided his force, weakening their ability to defend any particular position. He left some men at Fort Diego, sent a group across the bay to Anastasia Island, and encamped another on Point Quartell (modern-day Vilano Beach).
After much maneuvering on the English side, the most significant battle of the campaign took place in the early morning hours of June 15 (modern calendar June 26). A company of Scottish Highlanders and a number of Creeks had occupied the abandoned Fort Mose north of St. Augustine. Fort Mose was established in 1739 to defend the northern approach to the city; its defenders were free-blacks and escaped slaves organized into a militia unit. The African defenders of Fort Mose had left the four-square wooden and earthen structure in anticipation of Oglethorpe’s advance on the city, which never fully materialized aside from sporadic artillery fire.
Colonel Palmer, commanding the troops at Mose, warned the men to be on alert the evening of the 14th. He reportedly had heard “Spanish Indians dancing the War Dance.” Apparently the soldiers did not heed his call for vigilance and when the combined force of Spanish soldiers, African militia under the command of free-black Francisco Menendez, and Indian warriors attacked the fort, they easily routed the Highlanders and Creeks inside.
Conflicting reports surfaced on English causalities suffered at the Battle of Bloody Mose, as the event became known. Oglethorpe reported 20 Highlanders killed, plus “several Indians and some Others” as well as 27 taken prisoner. Thomas Jones, a Creek interpreter, counted “about fifty Whites and Indians” killed in the action. Jones also added gruesome details about the aftermath of the battle. “[A]fter their Victory at Moosa,” he explained, the victors “cut off the Heads and private Parts of the Slain, and carried them into Augustine in Triumph.”
The Battle of Bloody Mose proved to be a turning point in the siege. In the weeks that followed, Oglethorpe proved incapable of rallying his troops to the cause. By early July he had also lost the support of vessels patrolling the entrance to the Matanzas River. Citing possible hurricanes ships left the area, which allowed the Spanish to easily resupply the besieged settlement. By mid-July the English retreated and St. Augustine survived another British invasion.
The subsequent investigation by the General Assembly of South Carolina enumerated at length the failures of Oglethorpe’s expedition. First, unrestrained attacks by England’s Indian allies as well as preemptive raids near Amelia Island spoiled the element of surprise, long before the army marched into Florida. Second, the repeated marching and dividing of the troops without attacking weakened both morale and the potential for success. Third, several incidents alienated Oglethorpe’s Indian allies, without whom victory was unlikely. Fourth, the Assembly did not feel as if they had been properly advised on critical decisions during the campaign; Oglethorpe had acted without their advice and paid for it in defeat. Finally, the departure of the blockading vessels in early July dealt the final blow to an ill-conceived and poorly executed mission.
Ironically, Great Britain did gain control of St. Augustine 23 years later in 1763, following the end of the French and Indian War (1754-1763), also known as the Seven Years War. This time, a bloodless transfer took place and the British finally breached the city walls and entered the Castillo de San Marcos as victors.
To learn more about the investigation of Oglethorpe’s failed expedition, see John Tate Lanning, ed. The St. Augustine Expedition of 1740: A Report to the South Carolina General Assembly (Columbia: South Carolina Archives Department, 1954); on Fort Mose see Jane Landers, Black Society in Spanish Florida (Urbana: University of Illinois Press, 1999); on Creek – English relations, see Steven C. Hahn, The Invention of the Creek Nation, 1670-1763 (Lincoln: University of Nebraska Press, 2004).