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Raynald of Châtillon (c. 1124Plantilla:Spnd4 July 1187), also known as Reynald, Reginald, or Renaud, was a knight of French origin who became Prince of Antioch from 1153 to 1160 or 1161 and Lord of Oultrejordain from 1175 until his death. Antioch was a crusader state in the Near East, Oultrejordain a large fiefdom in the crusader Kingdom of Jerusalem, and he ruled both territories by right of one of his two wives. The second son of a French noble family, he joined the Second Crusade in 1147, and settled in Jerusalem as a mercenary. Six years later, he married Constance, Princess of Antioch, although her subjects regarded the marriage as a mesalliance.

Always in need of funds, Raynald tortured Aimery of Limoges, Latin Patriarch of Antioch who had refused to pay a subsidy to him. Raynald launched a plundering raid in Cyprus in 1156, causing great destruction in Byzantine territories. Four years later, Manuel I Komnenos, the Byzantine Emperor, led an army towards Antioch, forcing Raynald to accept Byzantine suzerainty. Raynald was raiding the valley of the river Euphrates in 1160 or 1161 when the governor of Aleppo captured him at Marash. He was released for a large ransom in 1176 but did not return to Antioch, because his wife had died in the interim. He married Stephanie of Milly, the wealthy heiress of Oultrejordain. Since Baldwin IV of Jerusalem had also granted Hebron to him, Raynald became one of the wealthiest barons in the Kingdom of Jerusalem. After Baldwin, who suffered from leprosy, made him regent in 1177, Raynald led the crusader army that defeated Saladin, the Muslim ruler of Egypt and Syria, at the Battle of Montgisard. In control of the caravan routes (or trade routes) between Egypt and Syria, he was the only Christian leader to pursue an offensive policy against Saladin, by making plundering raids against the caravans travelling near his domains. After Raynald's newly built fleet plundered the coast of the Red Sea, threatening the route of the Muslim pilgrims towards Mecca in early 1183, Saladin pledged that he would never forgive him.

Raynald was a firm supporter of Baldwin IV's sister, Sybilla, and her husband, Guy of Lusignan, during conflicts regarding the succession of the king. Sibylla and Guy were able to seize the throne in 1186 due to Raynald's co-operation with her uncle, Joscelin III of Courtenay. In spite of a truce between Saladin and the Kingdom of Jerusalem, Raynald attacked a caravan travelling from Egypt to Syria in late 1186 or early 1187, claiming that the truce was not binding upon him. After Raynald refused to pay compensation, Saladin invaded the kingdom and annihilated the crusader army in the Battle of Hattin. Raynald was captured on the battlefield. Saladin personally beheaded him for his brigandage and other crimes after he refused to convert to Islam. Most historians have regarded Raynald as an irresponsible adventurer whose lust for booty caused the fall of the Kingdom of Jerusalem. On the other hand, the historian Bernard Hamilton says that he was the only crusader leader who tried to prevent Saladin from unifying the nearby Muslim states.

The Principality of Antioch was a crusader state established by western European aristocrats in northern Syria and the fertile plains of Cilicia during the First Crusade. The First Crusade was declared at the Council of Clermont in 1095 by Pope Urban II against the Muslim Seljuk Turks for the rescue of the Christian Byzantine Empire and the liberation of Jerusalem. At a meeting at Constantinople, the crusader leaders promised Alexios I Komnenos, the Byzantine Emperor, that they would return to the Byzantine Empire all the lands that the Seljuks had conquered from the Byzantines. Although Antioch (now Antakya in Turkey) was one of the cities that the Byzantines had lost to the Seljuks, after capturing the city on 3 June 1098, the crusaders granted it to the Italo-Norman aristocrat Bohemond of Taranto, claiming that the Byzantines had failed to support them during the siege. As a consequence of the First Crusade, a further three crusader states—the County of Edessa, the Kingdom of Jerusalem, and the County of Tripoli—were founded in the Near East between 1098 and 1105.^[1]​ The Armenian warlords of the mountainous regions of Cilicia took advantage of the westerners' arrival to strengthen their position against the Byzantines and their Turkic neighbours. The Armenian Rubenids closely cooperated with the crusaders (or Franks) and often accepted the suzerainty of the princes of Antioch.^[2]​

Bohemond and his successors in Antioch, Tancred, Roger, Baldwin II of Jerusalem, and Bohemond II fought the Byzantines and the Muslim rulers of the cities of Aleppo and Shaizar (now both in Syria) to consolidate their rule.^[3]​^[4]​ The Byzantines did not abandon their claim to Antioch. Emperor Alexios forced Bohemond I to acknowledge Byzantine suzerainty over the principality in the Treaty of Devol in 1108 but the treaty was never implemented. In 1137, Alexios's son and successor John II Komnenos extracted an oath of fealty from Raymond of Poitiers who ruled Antioch as the husband and co-ruler of Bohemond II's only daughter Constance. The Byzantines also conquered Cilicia, and Raymond had to acknowledge the loss of the territory.^[5]​^[6]​

Occupying a narrow strip of land, the crusader states' survival depended on external support, and their leaders often appealed for help to the rulers of Catholic Europe.^[7]​ The balance of power drastically changed with the emergence of the talented Turkic military leader Zengi, who assumed power in Mosul (in present-day Iraq) in 1127, and in Aleppo in 1128.^[8]​^[9]​ Zengi captured the city of Edessa (now in Turkey) in late 1144. When Zengi died in 1146 his younger son Nur ad-Din succeeded him in Syria. Edessa's fall led to the Second Crusade which ended with an unsuccessful siege of Damascus in the summer of 1148. The remaining strongholds of the County of Edessa were sold to the Byzantine Empire in 1150.^[10]​

Raynald was the younger son of Hervé II, Lord of Donzy in France.^[11]​^[12]​ In older historiography, Raynald was described as the son of Geoffrey, Count of Gien,^{[note 1]}​^[14]​ but in 1989 Jean Richard demonstrated Raynald's kinship with the lords of Donzy. They were influential noblemen in the Duchy of Burgundy (in present-day western France), who claimed the Palladii (a prominent Gallo-Roman aristocratic family during the Later Roman period) were their ancestors.^[11]​^[15]​ Raynald's mother was an unnamed daughter of Hugh the White, lord of La Ferté-Milon.^[16]​

Raynald was born around 1124. He received the lordship of Châtillon-sur-Loire,^[11]​^[17]​ but a part of his patrimony was "violently and unjustly confiscated", according to one of his letters.^[18]​ He came to the Kingdom of Jerusalem before 1153, when he was mentioned as a mercenary fighting in the army of Baldwin III of Jerusalem.^[19]​ According to modern historians, he had joined the army of Louis VII of France during the Second Crusade.^[11]​ Louis departed from France in June 1147.^[20]​ The 12th-century historian William of Tyre, who was an enemy of Raynald, claimed that Raynald was "almost a common soldier".^[11]​ Louis VII left the Holy Land for France in the summer of 1149, but Raynald stayed behind in Palestine.^[11]​^[21]​

Raymond of Poitiers, the Prince of Antioch, and thousands of his soldiers fell in the Battle of Inab on 28 June 1148, leaving the principality almost undefended.^[22]​ Baldwin III of Jerusalem (who was the cousin of Raymond's widow, Constance, the ruling Princess of Antioch) came to Antioch at the head of his army at least three times during the following years. To secure the defence of the principality, Baldwin tried to persuade her to remarry, but she did not accept his candidates. She also refused John Roger, whom the Byzantine emperor, Manuel I Komnenos, had proposed to be her husband.^[23]​^[24]​

William of Tyre mentions that Raynald fought in Baldwin's army during the siege of Ascalon in early 1153.^[12]​ The historian Steven Runciman says that Raynald had already settled in Antioch, and was engaged to Constance before the siege began.^[14]​ In contrast, the historian Malcolm Barber says that their betrothal took place during a visit by Raynald to the principality before the end of the siege.^[18]​ They kept their betrothal a secret until Baldwin gave his permission for their marriage.^[14]​^[18]​ According to the historian Andrew D. Buck, they needed a royal permission because Raynald was in Baldwin's service.^[25]​ The early-13th-century chronicle known as the Estoire d'Eracles states that Baldwin happily consented to the marriage because it freed him from his obligation to "defend a land" (namely Antioch) "which was so far away" from his kingdom.^[26]​

After Baldwin granted his consent, Constance married Raynald.^[14]​^[18]​^[27]​ He was installed as prince in or shortly before May 1153.^[28]​ In that month, he confirmed the privileges of the Venetian merchants.^[29]​ William of Tyre records that his subjects were astonished that their "famous, powerful and well-born" princess condescended to "marry a kind of mercenary knight".^[19]​ No coins struck for Raynald have survived. According to Buck, this indicates that Raynald's position was relatively weak. Whereas Raymond of Poitiers had issued around half of his charters without a reference to Constance, Raynald always mentioned that he made the decision with his wife's consent. ^[30]​ Raynald did control appointments to the highest offices: he made Geoffrey Jordanis the constable and Geoffrey Falsard the duke of Antioch.^[31]​

The Norman chronicler Robert of Torigni writes that Raynald seized three fortresses from the Aleppans soon after his accession, but does not name them.^[32]​ Aimery of Limoges, the wealthy Latin patriarch of Antioch, did not hide his dismay at Constance's second marriage. He even refused to pay a subsidy to Raynald. In retaliation, Raynald captured and tortured Aimery in the summer of 1154,^[33]​ forcing him to sit naked and covered with honey in the sun, before imprisoning him. Aimery was only released on Baldwin III's demand, but he soon left his see for Jerusalem.^[27]​^[34]​ Surprisingly, Raynald was not excommunicated for his abuse of Aimery. Buck argues that Raynald could avoid the punishment because of Aimery's previous debates with the papacy over the Archbishopric of Tyre. Instead, Aimery excommunicated Raynald on the demand of the papacy in 1154 as a consequence of a conflict between Antioch and Genoa.^[35]​

Emperor Manuel sent his envoys to Antioch, proposing to recognize Raynald as the new prince if he launched a campaign against the Armenians of Cilicia, who had risen up against Byzantine rule. He also promised that he would compensate Raynald for the expenses of the campaign.^[27]​ After Raynald defeated the Armenians at Alexandretta in 1155, the Knights Templar took control of the region of the Syrian Gates that the Armenians had recently invaded.^[36]​ Although the sources are unclear, Runciman and Barber agree that it was Raynald who granted the territory to them.^[36]​^[34]​

Always in need of funds, Raynald urged Manuel to send the promised subsidy to him, but Manuel failed to pay the money.^[34]​ Raynald made an alliance with the Armenian lord Thoros II of Cilicia. They attacked Cyprus, plundering the prosperous Byzantine island for three weeks in early 1156.^[37]​^[38]​ With rumours spreading of an imperial fleet approaching the island, they left Cyprus, but only after they had forced all Cypriots to ransom themselves, with the exception of the wealthiest individuals (including Manuel's nephew, John Doukas Komnenos), whom they carried off to Antioch as hostages.^[37]​^[39]​

Taking advantage of the presence of Thierry, Count of Flanders, and his army in the Holy Land and an earthquake that had destroyed most towns in Northern Syria, Baldwin III of Jerusalem invaded the Muslim territories in the valley of the Orontes River in the autumn of 1157.^[40]​ Raynald joined the royal army, and they laid siege to Shaizar.^[39]​^[40]​ At this point, Shaizar was held by the Shi'ite Assassins, but before the earthquake it had been the seat of the Sunnite Munqidhites who paid an annual tribute to Raynald.^[40]​ Baldwin was planning to grant the fortress to Thierry of Flanders, but Raynald demanded that the count should pay homage to him for the town. After Thierry sharply refused to swear fealty to an upstart, the crusaders abandoned the siege.^[41]​ They marched on Harenc (present-day Harem, Syria), which had been an Antiochene fortress before Nur ad-Din captured it in 1150.^[42]​ After the crusaders captured Harenc in February 1158, Raynald granted it to the Flemish Raynald of Saint-Valery.^[41]​^[43]​

Emperor Manuel unexpectedly invaded Cilicia, forcing Thoros II to seek refuge in the mountains in December 1158.^[44]​^[45]​ Unable to resist a full-scale Byzantine invasion, Raynald hurried to Mamistra to voluntarily make his submission to the emperor.^[44]​^[43]​ On Manuel's demand, Raynald and his retainers walked barefoot and bareheaded through the streets of the town to the imperial tent where he prostrated himself, begging for mercy.^[46]​ William of Tyre stated that "the glory of the Latin world was put to shame" on this occasion, because envoys from the nearby Muslim and Christian rulers were also present at Raynald's humiliation.^[47]​ Manuel demanded that a Greek Patriarch be installed at Antioch. Although his demand was not accepted, documentary evidence indicates that Gerard, the Catholic bishop of Latakia was forced to move to Jerusalem.^[48]​ Raynald had to promise that he would allow a Byzantine garrison to stay in the citadel whenever it was required and would send a troop to fight in the Byzantine army.^[46]​ Before long, Baldwin III of Jerusalem persuaded Manuel to consent to the return of the Latin patriarch, Aimery, to Antioch, instead of installing a Greek patriarch. When the emperor entered Antioch with much pomp and ceremony on 12 April 1159, Raynald held the bridle of Manuel's horse.^[45]​^[49]​ Manuel left the town eight days later.^[50]​

Raynald made a plundering raid in the valley of the river Euphrates at Marash to seize cattle, horses and camels from the local peasants in November 1160 or 1161.^[51]​^[52]​^[53]​ Majd ad-Din, Nur ad-Din's commander of Aleppo, gathered his troops (10,000 people, according to the contemporary historian Matthew of Edessa), and attacked Raynald and his retinue on the way back to Antioch.^[51]​^[54]​ Raynald tried to fight, but the Muslim warriors unhorsed and captured him. He was sent to Aleppo where he was put in jail.^[52]​

Almost nothing is known about Raynald's life while he was imprisoned for fifteen years.^[47]​ He shared his prison with Joscelin III of Courtenay, the titular Count of Edessa, who had been captured a couple of months before him.^[55]​ In Raynald's absence, Constance wanted to rule alone, but Baldwin III of Jerusalem made Patriarch Aimery regent for her fifteen-year-old son (Raynald's stepson), Bohemond III of Antioch.^[55]​^[51]​ Constance died around 1163, shortly after her son reached the age of majority.^[56]​ Her death deprived Raynald of his claim to Antioch.^[47]​ However, he had become an important personality, with prominent family connections, as his stepdaughter, Maria of Antioch, married Emperor Manuel in 1161, and his own daughter, Agnes, became the wife of Béla III of Hungary.^[47]​

Nur ad-Din died unexpectedly in 1174. His underage son As-Salih Ismail al-Malik succeeded him, and Nur ad-Din's mamluk ('slave-soldier') Gümüshtekin assumed the regency for him in Aleppo. Being unable to resist attacks by the ambitious Kurdish warlord Saladin, Gümüshtekin sought the support of Raynald's stepson Bohemond III of Antioch, and on his request released Raynald along with Joscelin of Courtenay and all other Christian prisoners in 1176.^[57]​^[58]​ Raynald's ransom, fixed at 120,000 gold dinars, reflected his prestige.^[47]​ It was most probably paid by Emperor Manuel, according to Barber and Hamilton.^[59]​^[60]​

Raynald came to Jerusalem with Joscelin before 1 September 1176,^[61]​ where he became a close ally of Joscelin's sister, Agnes of Courtenay.^[62]​ She was the mother of the young Baldwin IV of Jerusalem, who suffered from leprosy.^[62]​^[63]​ Hugo Etherianis, who lived in Constantinople after about 1165, mentioned in the preface of his work About the Procession of the Holy Spirit, that he had asked "Prince Raynald" to deliver a copy of the work to Aimery of Limoges.^[64]​ Hamilton writes that these words suggest that Raynald led the embassy that Baldwin IV sent to Constantinople to confirm an alliance between Jerusalem and the Byzantine Empire against Egypt towards the end of 1176.^[64]​^[65]​

After his return from Constantinople early in 1177, Raynald married Stephanie of Milly, the lady of Oultrejordain, and Baldwin IV also granted him Hebron.^[66]​ The first extant charter styling Raynald as "Lord of Hebron and Montréal" was issued in November 1177.^[67]​ He owed service of 60 knights to the Crown, showing that he had become one of the wealthiest barons of the realm.^[66]​^[68]​ From his castles at Kerak and Montréal, he controlled the routes between the two main parts of Saladin's empire, Syria and Egypt.^[69]​ Raynald and Baldwin IV's brother-in-law, William of Montferrat, jointly granted large estates to Rodrigo Álvarez, the founder of the Order of Mountjoy, to strengthen the defence of the southern and eastern frontier of the kingdom.^[66]​ After William of Montferrat died in June 1177, the king made Raynald regent of the kingdom.^[70]​

Baldwin IV's cousin, Philip I, Count of Flanders, came to the Holy Land at the head of a crusader army in early August 1177.^[69]​ The king offered him the regency, but Philip refused the offer, saying that he did not want to stay in the kingdom.^[71]​ Philip declared that he was "willing to take orders" from anybody, but he protested when Baldwin confirmed Raynald's position as "regent of the kingdom and of the armies" as he thought that a military commander without special powers should lead the army.^[72]​ Philip left the kingdom a month after his arrival.^[73]​

Saladin invaded the region of Ascalon, but the royal army launched an attack on him in the Battle of Montgisard on 25 November, leading to his defeat.^[74]​ William of Tyre and Ernoul attributed the victory to the king, but Baha ad-Din ibn Shaddad and other Muslim authors recorded that Raynald was the supreme commander.^[75]​ Saladin himself referred to the battle as a "major defeat which God mended with the famous battle of Hattin",^[76]​ according to Baha ad-Din.^[77]​

Raynald signed a majority of royal charters between 1177 and 1180, with his name always first among signatories, showing that he was the king's most influential official during this period.^[78]​ Raynald became one of the principal supporters of Guy of Lusignan, who married the king's elder sister, Sybilla, in early 1180, although many barons of the realm had opposed the marriage.^[79]​^[80]​ The king's half sister, Isabella (whose stepfather, Balian of Ibelin, was Guy of Lusignan's opponent), was engaged to Raynald's stepson, Humphrey IV of Toron, in autumn 1180.^[79]​ Baldwin IV dispatched Raynald, along with Heraclius, the Latin Patriarch of Jerusalem, to mediate a reconciliation between Bohemond III of Antioch and Patriarch Aimery in early 1181.^[81]​^[82]​ The same year, Roupen III, Lord of Cilician Armenia, married Raynald's stepdaughter, Isabella of Toron.^[83]​

Raynald was the only Christian leader who fought against Saladin in the 1180s.^[84]​^[85]​ The contemporaneous Ernoul mentions two raids that Raynald made against caravans travelling between Egypt and Syria, breaking the truce.^[86]​ Modern historians debate whether Raynald's military actions sprang from a desire for booty,^[87]​ or were deliberate maneuvers to prevent Saladin from annexing new territories.^[85]​ After As-Salih died on 18 November 1181, Saladin tried to seize Aleppo, but Raynald stormed into Saladin's territory, reaching as far as Tabuk on the route between Damascus and Mecca.^[88]​ Saladin's nephew, Farrukh Shah, invaded Oultrejordain instead of attacking Aleppo to compel Raynald to return from the Arabian Desert.^[89]​ Before long, Raynald seized a caravan and imprisoned its members.^[89]​ On Saladin's protest, Baldwin IV ordered Raynald to free them, but Raynald refused.^[90]​ His defiance annoyed the king, enabling Raymond III of Tripoli's partisans to reconcile him with the monarch.^[91]​ A close relative of Baldwin, Raymond had assumed the regency for him in 1174 but he was banned from the kingdom for allegedly plotting against the ailing king.^[92]​ Raymond's return to the royal court put an end to Raynald's paramount position. After accepting the new situation, Raynald cooperated with the king and Raymond during the fights against Saladin in the summer of 1182.^[93]​

Saladin revived the Egyptian naval force and tried to capture Beirut, but his ships were forced to retreat.^[94]​ Raynald ordered the building of at least five ships in Oultrejordain. They were carried across the Negev desert to the Gulf of Aqaba at the northern end of the Red Sea in January or February 1183.^[95]​^[96]​^[97]​ He captured the fort of Ayla (present-day Eilat in Israel), and attacked the Egyptian fortress on Ile de Graye. Part of his fleet made a plundering raid along the coasts against ships delivering Muslim pilgrims and goods, threatening the security of the holy cities of Mecca and Medina.^[95]​^[98]​ Raynald left Ile de Graye, but his fleet continued the siege.^[99]​ Saladin's brother, Al-Adil, the governor of Egypt, dispatched a fleet to the Red Sea. The Egyptians relieved Ile de Graye and destroyed the Christian fleet. Some of the soldiers were captured near Medina because they landed either to escape or to attack the city. Raynald's men were executed, and Saladin took an oath that he would never forgive him.^[99]​^[100]​ Though Raynald's naval expedition "showed a remarkable degree of initiative" according to Hamilton, most modern historians agree that it contributed to the unification of Syria and Egypt under Saladin's rule.^[101]​ Saladin captured Aleppo in June 1183, completing the encirclement of the crusader states.^[102]​

Baldwin IV, who had become seriously ill, made Guy of Lusignan regent in October 1183.^[103]​ Within a month, Baldwin dismissed Guy, and had Guy's five-year-old stepson, Baldwin V, crowned king in association with himself.^[104]​ Raynald was not present at the child's coronation, because he was at the wedding of his stepson, Humphrey, and Baldwin IV's sister, Isabella, in Kerak.^[105]​ Saladin unexpectedly invaded Oultrejordain, forcing the local inhabitants to seek refuge in Kerak.^[105]​ After Saladin broke into the town, Raynald only managed to escape to the fortress because one of his retainers had hindered the attackers from seizing the bridge between the town and the castle.^[106]​ Saladin laid siege to Kerak.^[107]​ According to Ernoul, Raynald's wife sent dishes from the wedding to Saladin, persuading him to stop bombarding the tower where her son and his wife stayed.^[107]​ After envoys from Kerak informed Baldwin IV of the siege, the royal army left Jerusalem for Kerak under the command of the king and Raymond III of Tripoli.^[107]​ Saladin abandoned the siege before their arrival on 4 December.^[107]​ On Saladin's order, Izz al-Din Usama had a fortress built at Ajloun, near the northern border of Raynald's domains.^[108]​

Baldwin IV died in early 1185.^[95]​ His successor, the child Baldwin V, died in late summer 1186.^[109]​ The High Court of Jerusalem had ruled that neither Baldwin V's mother, Sybilla (who was Guy of Lusignan's wife), nor her sister, Isabella (who was the wife of Raynald's stepson), could be crowned without the decision of the pope, the Holy Roman Emperor, and the kings of France and England on Baldwin V's lawful successor.^[110]​ However, Sybilla's uncle, Joscelin III of Courtenay, took control of Jerusalem with the support of Raynald and other influential prelates and royal officials.^[111]​^[112]​ Raynald urged the townspeople to accept Sybilla as the lawful monarch, according to the Estoire d'Eracles.^[113]​ Raymond III of Tripoli, and his supporters tried to prevent her coronation and reminded her partisans of the decision of the High Court.^[114]​ Ignoring their protest, Raynald and Gerard of Ridefort, Grand Master of the Knights Templar, accompanied Sybilla to the Holy Sepulchre, where she was crowned.^[114]​ She also arranged the coronation of her husband, although he was unpopular even among her supporters.^[115]​^[116]​ Her opponents tried to persuade Raynald's stepson, Humphrey, to claim the crown on his wife's behalf, but Humphrey deserted them and swore fealty to Sybilla and Guy.^[117]​^[116]​ Raynald headed the list of secular witnesses in four royal charters issued between 21 October 1186 and 7 March 1187, showing that he had become a principal figure in the new king's court.^[118]​

Ali ibn al-Athir and other Muslim historians record that Raynald made a separate truce with Saladin in 1186.^[108]​ This "seems unlikely to be true", according to Hamilton, because the truce between the Kingdom of Jerusalem and Saladin legally covered Raynald's domains as they formed a large fiefdom in the kingdom.^[108]​ In late 1186 or early 1187, a rich caravan travelled through Oultrejordain from Egypt to Syria.^[108]​ Ali ibn al-Athir mentioned that a group of armed men accompanied the caravan.^[119]​ Raynald seized the caravan, possibly because he regarded the presence of soldiers as a breach of the truce, according to Hamilton.^[120]​^[121]​ He took all the merchants and their families prisoner, seized a large amount of booty, and refused to receive envoys from Saladin demanding compensation.^[121]​^[122]​ Saladin sent his envoys to Guy of Lusignan, who accepted his demands.^[121]​ However, Raynald refused to obey the king, stating in the words of the Estoire d'Eracles that "he was lord of his land, just as Guy was lord of his, and he had no truces with the Saracens". For Barber, Raynald's disobedience indicates that the kingdom was "on the brink of breaking up into a collection of semi-autonomous fiefdoms" under Guy's rule.^[121]​ Saladin proclaimed a jihad (or holy war) against the kingdom, taking an oath that he would personally kill Raynald for breaking the truce.^[123]​

The Estoire d'Eracles incorrectly claims that Saladin's sister was also among the prisoners taken by Raynald when he seized the caravan.^[108]​^[122]​ She had already returned from Mecca to Damascus in a separate pilgrim caravan in March 1187.^[108]​ To protect her against an attack by Raynald, Saladin escorted the pilgrims while they were travelling near Oultrejordain.^[125]​ Saladin stormed into Oultrejordain on 26 April and pillaged Raynald's domains for a month.^[126]​ Thereafter, Saladin marched to Ashtara on the road between Damascus and Tiberias, where the troops coming from all parts of his realm assembled.^[127]​^[128]​

The Christian forces assembled at Sepphoris.^[127]​^[129]​ Raynald and Gerard of Ridefort persuaded Guy of Lusignan to take the initiative and attack Saladin's army, although Raymond III of Tripoli had tried to persuade the king to avoid a direct fight with it.^[119]​^[130]​ During the debate, Raynald accused Raymond of Tripoli of co-operating with the enemy.^[131]​ Saladin inflicted a crushing defeat on the crusaders in the Battle of Hattin on 4 July.^[132]​ Most commanders of the Christian army were captured on the battlefield.^[133]​

Guy of Lusignan and Raynald were among the prisoners who were brought before Saladin.^[134]​ Saladin handed a cup of iced rose water to Guy.^[135]​ After drinking from the cup, the king handed it to Raynald.^[135]​ Imad ad-Din al-Isfahani (who was present) recorded that Raynald drank from the cup.^[134]​ Since customary law prescribed that a man who gave food or drink to a prisoner could not kill him, Saladin stated that it was Guy who had given the cup to Raynald.^[135]​ Saladin called Raynald to his tent.^[134]​ He accused him of many crimes (including brigandage and blasphemy), offering him to choose between conversion to Islam or death, according to Imad ad-Din and Ibn al-Athir.^[119]​^[135]​ After Raynald flatly refused to convert, Saladin took a sword and struck Raynald with it.^[119]​^[135]​ As Raynald fell to the ground, Saladin beheaded him.^[119]​^[136]​ The reliability of the reports of Saladin's offer to Raynald is subject to scholarly debate, because the Muslim authors who recorded them may have only wanted to improve Saladin's image.^[137]​ Ernoul's chronicle and the Estoire d'Eracles recount the events ending with Raynald's execution in almost the same language as the Muslim authors.^[135]​ However, according to Ernoul's chronicle, Raynald refused to drink from the cup that Guy of Lusignan handed to him.^[134]​^[138]​ According to Ernoul, Raynald's head was struck off by Saladin's mamluks and it was brought to Damascus to be "dragged along the ground to show the Saracens, whom the prince had wronged, that vengeance had been exacted".^[139]​^[138]​ Baha ad-Din also wrote that Raynald's fate shocked Guy of Lusignan, but Saladin soon comforted him, stating that "A king does not kill a king, but that man's perfidy and insolence went too far".^[140]​

Raynald's first wife, Constance of Antioch (born in 1128), was the only daughter of Bohemond II of Antioch and Alice of Jerusalem.^[141]​ Constance succeeded her father in Antioch in 1130.^[142]​ She was given in marriage to Raymond of Poitiers in 1136.^[143]​ The widowed Constance's marriage to Raynald is described as "the misalliance of the century" by Hamilton,^[144]​ but Buck emphasises that "the marriage went unmentioned in Western chronicles".^[25]​ Buck adds that Raynald's relatively low birth "actually made him the ideal candidate" to marry the widowed princess who had a son with a strong claim to rule upon reaching the age of majority, and Raynald was possibly "expected to eventually step aside".^[145]​

Their daughter, Agnes, moved to Constantinople in early 1170 to marry Kaisar Alexios-Béla, the younger brother of Stephen III of Hungary, who lived in the Byzantine Empire.^[146]​ Agnes was renamed Anna in Constantinople.^[147]​ Her husband succeeded his brother as Béla III of Hungary in 1172.^[148]​ She followed her husband to Hungary, where she gave birth to seven children before she died around 1184.^[147]​ Raynald and Constance's second daughter, Alice, became the third wife of Azzo VI of Este in 1204.^[149]​ Raynald also had a son, Baldwin, from Constance, according to Hamilton and Buck, but Runciman says that Baldwin was Constance's son from her first husband.^[150]​^[151]​^[152]​ Baldwin moved to Constantinople in the early 1160s.^[56]​ He died fighting at the head of a Byzantine cavalry regiment in the Battle of Myriokephalon on 17 September 1176.^[153]​

Raynald's second wife, Stephanie of Milly, was the younger^[154]​ daughter of Philip of Milly, Lord of Nablus, and Isabella of Oultrejordain.^[155]​ She was born around 1145.^[156]​ Her first husband, Humphrey III of Toron, died around 1173.^[157]​ She inherited Oultrejordain from her niece, Beatrice Brisbarre, shortly before she married Miles of Plancy in early 1174.^[157]​ Miles of Plancy was murdered in October 1174.^[158]​^[154]​

Most information on Raynald's life was recorded by Muslim authors, who were hostile to him.^[159]​ Baha ad-Din ibn Shaddad described him as a "monstrous infidel and terrible oppressor"^[160]​ in his biography of Saladin.^[161]​ Saladin compared Raynald with the king of Ethiopia who had tried to destroy Mecca in 570 and was called the "Elephant" in the Surah Fil of the Quran.^[162]​ Ibn al-Athir described him as "one of the most devilish of the Franks, and one of the most demonic", adding that Raynald "had the strongest hostility to the Muslims".^[163]​

Most Christian authors who wrote of Raynald in the 12th and 13th centuries were influenced by Raynald's political opponent, William of Tyre.^[159]​ The author of the Estoire d'Eracles stated that Raynald's attack against a caravan at the turn of 1186 and 1187 was the "reason of the loss of the Kingdom of Jerusalem".^[108]​ Modern historians have usually also treated Raynald as a "maverick who did more harm to the Christian than to the [Muslim] cause" (Hamilton).^[159]​ Runciman describes him as a marauder who could not resist the temptation presented by the rich caravans passing through Oultrejordain.^[87]​ He argues that Raynald attacked a caravan during the 1180 truce because he "could not understand a policy that ran counter to his wishes".^[87]​

Some Christian authors regarded Raynald as a martyr for the faith.^[119]​ After learning of Raynald's death from King Guy's brother Geoffrey of Lusignan, Peter of Blois dedicated a book (entitled Passion of Prince Raynald of Antioch) to him shortly after his death. The Passion underlines that Raynald defended the True Cross at Hattin. ^[119]​ Among modern historians, Hamilton describes Raynald as "an experienced and responsible crusader leader" who made several attempts to prevent Saladin from uniting the Muslim realms along the borders of the crusader states.^[164]​ The historian Alex Mallett refers to Raynald's naval expedition as "one of the most extraordinary episodes in the history of the Crusades, and yet one of the most overlooked".^[163]​