The west side – occupied by the town of Gibraltar, which stands at the base of the Rock – and the northern approach across the isthmus have been densely fortified by its various occupants with numerous walls, towers and gun batteries.
King Ferdinand I of Castile began a siege of Algeciras on the other side of the bay in July, but his naval blockade was unable to stop supplies being smuggled in small boats from Gibraltar to the besieged city.
[7] The Moorish presence in Gibraltar ended in 1462, when Enrique's son Juan Alonso de Guzmán, 1st Duke of Medina Sidonia captured it after the eighth siege.
The Duke of Medina Sidonia claimed Gibraltar as his own, making a mortal enemy of Juan Ponce de León, Count of Arcos, but Henry IV of Castile declared it crown property shortly afterwards and so began a civil war.
Medina Sidonia's grandson, the third duke Juan Alfonso Pérez de Guzmán, was responsible for Gibraltar's tenth siege (and, as it happened, its last for 200 years).
Queen Isabella I again declared Gibraltar crown property in 1501, but her death three years later left Castile in turmoil, prompting Medina Sidonia to take advantage of the kingdom's weakness.
It was initially assumed that Britain would not permanently retain Gibraltar, and would eventually trade it for something else, but the strength of British public opinion made it politically impossible to use the territory as a bargaining chip.
The issue came to a head in 1727 when King Philip V of Spain claimed that the British had voided Article X of the treaty, under which Gibraltar had been ceded, due to failures to adhere to its conditions.
[14] In the years following the thirteenth siege, tensions began to resurface between Britain and France,[15] and Spain remained neutral in a series of wars waged over the two nations' rival ambitions.
[18] Throughout the siege, the Spanish attempted to starve the garrison into submission by blockading the isthmus and bribing the Sultan of Morocco into cutting off supplies while bombarding the town and its fortifications.
The Great Siege was noteworthy for the efforts of engineers on both sides to gain advantage through the adoption of novel technologies, such as the Spanish floating batteries and the British depressing carriages to allow cannon to fire downwards from the Rock of Gibraltar.