Calatrava, the only important city in the Guadiana River valley, which thus guards the roads to Córdoba and Toledo, had been conquered in 1147 by Alfonso VII, becoming one of the farthest Christian outposts during this stage of the reconquista.

The castle had been placed under the protection of the Knights Templar, but this had proved unsatisfactory, and Sancho III of Castile had made an offer: he would grant the town and fortress of Calatrava to anyone who promised to defend it from the Moors.

Encouraged by a friar named Diego Velásquez, who had been a warrior before becoming a friar, Raymond, abbot of the Fitero Abbey, takes up the challenge.

Sancho grants them the privilege of defending Calatrava, and Raymond organizes an army, with the support of Juan II of Toledo, the Archbishop of Toledo, that successfully prevents the Moors from attacking this place in 1158.

It is the founding moment of the Order of Calatrava, the spearhead of the Iberian armies during the Reconquista.