Gerald the Fearless

 The city of Évora honours Gerald with a place on its coat-of-arms. The central plaza, the Praça do Giraldo, is also named after him.

Gerald or Gerard the Fearless (died prob. 1173), known in Portuguese as Geraldo Geraldes Sempavor ("without fear"), was a Portuguese warrior and folk hero of the Reconquista whose theatre of operations was in the barren Alentejo and Extremadura regions of the lower Guadiana river. The city of Évora was the most lasting of his conquests and was never retaken. His success and independence have suggested parallels with the Castilian hero El Cid and Gerald has been called "the Cid of Portugal".

Reconquista in Alentejo and Extremadura
Around 1162 Gerald assembled a private army (a mesnada) and rapidly developed tactics that proved remarkably successful in seizing Muslim strongholds, though it was not adapted for siege warfare. He "perfected techniques of nocturnal surprise in wintry or stormy weather, stealthy escalading of walls by picked commando-like troops, cutting down of sentries and opening of town gates to the larger force stationed without." Among the primary sources for Gerald's methods the most important is the contemporary Arabic chronicler Ibn Ṣāḥib al-Ṣalā, whose Al-Mann bil-Imāma was incorporated into the history of al-Maqqarī in the seventeenth century. His opinion of Gerald and his tactics is very low: The dog [Gerald] marched on rainy and very dark nights, with strong wind and snow, towards the cities and, having prepared his wooden instruments of scaling [walls] very large, so that they would surpass the wall of the city, he would apply those ladders to the side of the tower and catch the sentinel [by surprise] and say to him: "Shout, as is your custom," in order that the people would not hear him. When the scaling of the group had been completed on the highest wall in the city, they shouted in their language with an abominable screech, and they entered the city and fought whom they found and robbed them and captured all who were there in [the city, taking] captive and prisoner all who were there.

Of the places Gerald conquered the primary sources are in general agreement, also as to the order of their seizure, but as to the dating of events there is ambiguity. Ibn Ṣāḥib's version goes: In the second Jumada al-awwal [15 April–13 May] of the anno Hegirae 560 [1165] the city of Trujillo was surprised, and in Dhu al-Qi'dah the notable village of Évora. Also was the population of Cáceres in Safar 561 [1166], and the castle of Montánchez in Jumada al-thani and the strongholds of Serpa and Juromenha. The years 560 and 561 correspond roughly to the annos Domini 1165 and 1166, but here Ibn Ṣāḥib is almost certainly off in his dating by a year. The events rather took place in 1164 and 1165. A later Portuguese chronicle, the Crónica dos Godos ("Chronicle of the Goths"), dates the conquest of Évora to the year 1204 of the Spanish era, that is, 1166. Trujillo was taken on 14 May 1164, or in June; Évora in September 1164; and Cáceres in December 1164 or, on a later dating, in September 1166. These were the major conquests. The lesser conquests of Montánchez, Serpa, and Juromenha took place in 1165, based on Ibn Ṣāḥib's scheme, but Montánchez and Serpa may have gone in March 1167, as one historian has it. All the primary sources agree that Santa Cruz de la Sierra was the last of Gerald's successes, which may place it as late as 1169, though perhaps earlier (1167/8), along with Ureña. The conquest of these last two places left Gerald in a position to harass Beja. The date of the capture of Monfragüe, which was certainly one of his conquests, cannot be established.

Conflict with León
So successful was Gerald by 1168 that his eastward expansion threatened the southward expansion of the Kingdom of León. These actions were in violation of the succession arrangements laid down by Alfonso VII at Sahagún, since they comprised lands whose conquest had been assigned to León. A few of Gerald's conquests in the far east had even been assigned to Castile. The Leonese king, Ferdinand II, son of Alfonso VII, took action immediately after the taking of Cáceres, probably early in the spring of 1166, capturing Alcántara later that year and thus securing a crossing over the Tagus. Subsequently he allied with the Almohad caliph Yusuf I, who had warned him of Gerald and the Portuguese's encroachments on his interests.

In the early summer of 1169, Gerald took taifa and city of Badajoz after a long siege, but the garrison took refuge in the citadel, the alcazaba, the siege of which continued. Seeing an opportunity to add to his domains the chief city of the region at the expense of both his Muslim and Christian enemies, Afonso I of Portugal came with an army to Badajoz to relieve his nominal vassal. This provoked the opposition of Ferdinand of León, who claimed Badajoz as his own and came south with an army at the request of Yusuf, who had already sent a contingent of 500 cavalry to assist the garrison. The besieging Portuguese were themselves besieged by the Leonese and fighting broke out in the streets. While trying to flee, Afonso was caught on the hinge of a gate and flung from his horse, breaking his leg. He was captured by Ferdinand's men, while Gerald was captured by the Leonese majordomo, Fernán Ruiz de Castro, called el Castellano ("the Castilian"). He was an important person at court, who for a while held the highest military post in the capital (tenente turris Legionis, "possessing the tower of León"). He was the king's brother-in-law, being married to Stephanie the Unfortunate, an illegitimate daughter of Alfonso VII by his second mistress, Urraca Fernández, and thus a half-sister of Ferdinand II. After the mêlée the Leonese had control of the town and the alcazaba, which they soon relinquished to their Muslim allies. Ferdinand succeeded in gaining the valley of the upper Limia and the regions of Toroño (around Tuy), Capraria (around Verín), and Lobarzana (around Chaves) from Afonso in exchange for his release. Several of Gerald's conquests were ceded to purchase his freedom. Ferdinand retained Cáceres, but Trujillo, Montánchez, Santa Cruz de la Sierra, and Monfragüe he gave to Fernán Ruiz.

Serving the Almohads
In 1171 and 1172, while Yusuf was waging war on Valencia and Murcia, general anarchy prevailed in the Extremadura as Leonese, Portuguese, and Almohad troops fought for supremacy. Gerald took advantage of Yusuf's absence to conquer Beja in the Alentejo (1172). When he and Afonso disagree over whether to hold the site or raze it, Gerald—"impoverished and bereft of all aid" —went to Seville to put himself in the service of the caliph. To keep him away from Portugal he was sent to Morocco with 350 troops. There he received the governorship of al-Sūs (the desert of the southern Maghreb), but soon entered into negotiations with his former monarch concerning the use of al-Sūs as a base for a Portuguese invasion. When his correspondence was intercepted, he was arrested and put to death. The Chronica latina regum castellae, a Latin Christian chronicle, summarises Gerald's career in one paragraph at the end of its tenth chapter: Also then [at the capture of Afonso I at Badajoz] was captured Gerald, alias "without fear", who was given over to Rodrigo Fernández [sic], the Castilian, to whom, in exchange for his liberty, Gerald handed over Montánchez, Trujillo, Santa Cruz de la Sierra, and Monfragüe, which the same Gerald had gained from the Saracens, to whom he had caused much damage, and by whom he was decapitated in Moroccan territory on a laughable pretext. The chief source for Gerald's negotiations with the caliph and his death in Morocco is Ibn `Idhārī al-Marrākushī's Al-Bayān al-Mugrib. Many of the cities and castles that Gerald captured with ease were later re-conquered by the Almohads, who improved their fortifications so much that they were not taken by the Christians again until the next century. Cáceres was besieged four times without success (1184, 1213, 1218, and 1222) and is usually referred to as a castrum famossum ("famous castle") or muy fuerte castillo ("very strong castle") in Christian sources, although it had fallen relatively easily to Gerald. Trujillo was not taken by the Christians again until 1234. The defences of Badajoz were completely reworked after 1169 and those that survive today are almost entirely of the Almohad period; the city only fell to the Christians permanently in 1226.

 The dauntless Gerald: in his left he bears  Two watchmen's heads, his right the falchion rears:   The gate he opens, swift from ambush rise   His ready bands, the city falls his prize:   Évora still the grateful honour pays,   Her banner'd flag the mighty deed displays:   There frowns the hero; in his left he bears   The two cold heads, his right the falchion rears. —Camoens, The Lusiads           (Canto VIII, 21)

Legacy and legend
Gerald left his mark on the toponymy of the Extremadura. A document of the Order of Calatrava of 1218 refers to the cabeza de giraldo ("head of Gerald") as a place, without indicating where it lay. Two streams, the Geradillo and the Geraldo, the first flowing from the second and into the Tagus, are also named after Gerald. The region where the stream originates is in the highlands around Casas de Miravete, which is quite possibly the site of the cabeza.

The legends which later arose surrounding Gerald are given concise retelling by Louis-Adrien Duperron de Castera, a French translator: He was a man of rank, who, in order to avoid the legal punishment to which several crimes rendered him obnoxious, put himself at the head of a party of freebooters. Tiring, however, of that life, he resolved to reconcile himself to his sovereign by some noble action. Full of this idea, one evening he entered Évora, which then belonged to the Moors. In the night he killed the sentinels of one of the gates, which he opened to his companions, who soon became masters of the place. This exploit had its desired effect. The king pardoned Gerald, and made him governor of Évora. A knight with a sword in one hand, and two heads in the other, from that time became the armorial bearing of the city.