Gerald the Fearless 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 , 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 . 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 , 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 .