Sir Francis Drake's expedition against Cartagena de Indias in 1586 was a pivotal military maneuver amidst the ongoing Anglo-Spanish conflicts. Cartagena, located on the northern coast of present-day Colombia, served as a crucial Spanish port for transatlantic trade, particularly for treasure shipments from the Americas to Spain. In February of that year, Drake, with a fleet of approximately 30 ships and a force of around 2,000 men, aimed to disrupt Spanish commerce and project English strength in the Caribbean.

Drake's attack unfolded over a protracted siege, marked by intense naval encounters and ground assaults. The English forces faced stiff resistance from the well-fortified Spanish defenders, yet through strategic planning and persistence, they managed to breach the city's defenses. After capturing Cartagena, Drake held the city for nearly two months, successfully negotiating a ransom for its release. During this time, significant plunder from the city included valuable cargo, wealth from the treasury, and resources that would greatly benefit the English crown.

The aftermath of Drake's occupation underscored both the military might of England and the precarious nature of Spanish colonial operations in the Americas. This incident reflected a broader pattern of piracy and privateering that characterized the late 16th century, influencing maritime law and colonial policies in the wake of Drake’s exploits. The capture was not merely a tactical victory but also a symbolic blow to Spanish imperial pride, showcasing the vulnerability of their New World possessions.