Governor James Oglethorpe, motivated by territorial ambition and the urge to expand British influence in North America, initiated a military campaign against Spanish Florida in 1740. St. Augustine, as the oldest continuously inhabited European-established settlement in the continental United States, was identified as a key objective due to its strategic location along the Atlantic coast. Oglethorpe aimed not only to secure the area for the British Empire but also to disrupt Spanish operations and trade routes in the region.

The siege began with Oglethorpe leading a combined force of approximately 1,500 soldiers, consisting of British troops from the Georgia colony and their Native American allies. They laid siege to the heavily fortified city of St. Augustine, undertaking artillery bombardments and infantry assaults. Throughout the siege, the defenders, numbering around 500 Spanish troops reinforced by local militia and indigenous allies, showed resilience, managing to withstand the assaults.

Despite Oglethorpe’s determination and initial successes in skirmishing, the prolonged siege proved challenging. Supply lines became strained, morale dropped among the attackers, and the Spanish forces utilized their superior fortifications effectively. After nearly two months of siege, Oglethorpe ordered a withdrawal, marking a significant military setback for British forces in their attempts to expand territory southward. The failed campaign against St. Augustine symbolized the complexities and dangers of colonial warfare during that era.