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The Romans were the first to single out this site as a strategic crossroads near the geographical centre of the Iberian Peninsula; ancient Toletum became an important way-station in Roman Hispania. By the 6th century, Roman influence was already a distant memory and Visigothic King Atanagild moved the site of his capital from Seville to Toletum, thus creating the Catholic heartland of the Visigothic kingdom. Over time, endless feuds between Visigothic nobles sent the kingdom into decline and its capital became vulnerable. As a result, the Muslims conquered Toledo with little difficulty after crossing the Straits of Gibraltar in 711.

Toledo rapidly grew to be the most important city of central Muslim Spain and, after the collapse of the caliphate in Córdoba in 1031, became the capital of an independent Arab taifa (small kingdom). For the following 50 years the city was unrivalled as a centre of learning and arts in Spain and, for a brief period, its power ranged across all modern Castilla-La Mancha extending to Valencia and even to Córdoba.

Alfonso VI marched into Toledo in 1085, marking a significant victory on the long road of the Reconquista. Shortly thereafter, the Vatican recognised Toledo as a seat of the Church in Spain. In the centuries that followed, the city was one of the primary residences of choice for the Castilian monarchy. Its alliance with the archbishop of Toledo, a vocal proponent of the Reconquista and the monarchs’ right-hand man at this time, ensured that Toledo became a place of considerable power. Initially, Toledo’s Christians, Jews and Muslims coexisted tolerably well. However, soon after Granada fell to the Catholic Monarchs (Reyes Católicos) in 1492, Spain’s Muslims and Jews were compelled to convert to Christianity or flee; a grievous tragedy in this city of many faiths.

In the 16th century, Carlos I considered making Toledo his permanent capital, but his successor, Felipe II, dashed such ideas with his definitive move to Madrid, and Toledo went into decline.

In the early months of the 1936–39 civil war, Nationalist troops (and some civilians) were kept under siege in the Alcázar, but were eventually relieved by a force from the south. However, by diverting his units to Toledo, Franco missed an opportunity to reach Madrid before the arrival of the International Brigades, a miscalculation that many believe prolonged the war.

In 1986 Unesco declared the city a monument of world interest. Despite this, people are abandoning the old city for the characterless but comfortable modern suburbs sprawled out beneath it, leaving behind public servants, tourists, the rent-protected elderly and a medieval city in urgent need of attention.