Raymond III, Count of Tripoli

Melisende's son Baldwin III of Jerusalem (r. 1143–1163), who was staying in Tripoli when Raymond II was murdered, recalled the widowed Hodierna to the town.[7][8] Baldwin held an assembly after the burial at which the nobles of the County of Tripoli paid homage to Hodierna and her two minor children, Raymond and Melisende.[7] Raymond II had decreed that the master (or head) of the Knights Hospitaller in the county was to administer Tripoli if an underage count mounted the throne.[2] Baldwin ignored the late count's instructions in appointing Hodierna to the regency for her son.[2]

The teenage Raymond spent several years at the royal court in Jerusalem.[9] The first extant document that he witnessed in the royal capital was issued on 23 September 1152 or 1153.[9] Historian Kevin J. Lewis proposes that Baldwin III probably supervised Raymond's knightly education.[10]

Raymond reached the age of majority in 1155.[9] In his first extant charter, issued on 11 June 1157, he confirmed his father's diploma about the grant of Tortosa (now Tartus in Syria) to the Knights Templar.[9] Nur ad-Din, the Zengid ruler of Aleppo and Damascus (r. 1146–1174), ambushed Baldwin III at Jacob's Fort on the Jordan River eight days later.[11] Hundreds of Christian soldiers were captured or killed, and the king was forced to flee to Safed.[12] After Nur ad-Din laid siege to Baniyas, Baldwin III sent envoys to Tripoli and Antioch to seek assistance from Raymond and Raynald of Châtillon (r. 1153–1160).[10] They hurried to Chastel Neuf (at present-day Margaliot in Israel) to join the decimated royal army.[13][10] After their arrival, Nur ad-Din lifted the siege and withdrew his troops without resistance.[13][10]

An earthquake destroyed Tripoli, Arqa and Krak des Chevaliers in August 1157.[10] Taking advantage of the arrival of Thierry, Count of Flanders (r. 1128–1168) at the head of a sizeable army in October, Baldwin III, Raynald of Châtillon and Raymond decided to launch a joint campaign against the Muslim towns of North Syria which had also been ruined by the catastrophe.[10][14] The crusaders first attacked Chastel Rouge near the border of the County of Tripoli, but they could not force the defenders to surrender.[15] They could not seize Shaizar, either; Thierry of Flanders and Raynald of Châtillon claimed the town even before it was occupied, and they could not reach a compromise.[16][17] The siege of Harenc (now Harem in Syria) was a success, but the crusading leaders finished the campaign after they captured it in January 1158.[17][18]

Seeking a wife from the crusader states, the widowed Byzantine emperor Manuel I Komnenos (r. 1143–1180) sent envoys to Baldwin III in 1160.[19] Manuel said that he was willing to marry Maria of Antioch or Raymond's sister, Melisende, who were both closely related to the king.[20] Baldwin proposed Melisende, and the emperor acknowledged his choice.[20] Twelve galleys were built at Raymond's order, because he wanted to have a magnificent retinue for his sister during his voyage to Constantinople.[20] Their mother and aunt spent a considerable amount of money to buy precious jewelry for the future empress.[21] The emperor then changed his mind and began negotiations about his marriage to Maria with her mother, Constance of Antioch (r. 1130–1163).[22][23] Feeling slighted for himself and his sister, Raymond crewed his newly built fleet with criminals and sent them to raid the Byzantine coasts and islands in August 1161.[23][24] The pirates captured and plundered sacred places, and attacked pilgrims.[24]

Nur ad-Din raided Krak des Chevaliers and laid siege to Harenc in the summer of 1164.[25] Raymond marched out to join the crusaders (who were assembling to relieve the fortress),[26] but they were defeated in the ensuing battle on 10 August.[27] Thousands of crusaders fell during the battle and Raymond, Bohemond III of Antioch (r. 1163–1201), Joscelin III of Edessa, Hugh VIII of Lusignan and other commanders were captured.[27][28]

The crusader states in 1165

The crusader leaders captured at Harenc were taken to Aleppo, where they were imprisoned.[28][29] William of Tyre's report about Raymund's captivity is contradictory.[28] He claimed that Raymond had spent his imprisonment "in beggary and iron", but he also emphasized that Raymond had learnt to read and acquired a high level of education in the prison.[28] Modern historians assume, without positive evidence, that Raymond also learnt Arabic during his captivity.[30] Raymond instructed his "loyal vassals" to acknowledge Amalric of Jerusalem (r. 1163–1174), who had succeeded Baldwin III, as the lawful ruler of Tripoli for the duration of his captivity.[30] Amalric hurried to Tripoli[31] and took full responsibility for its government, assuming the title of "administrator of the county of Tripoli".[30] He could persuade Nur ad-Din to release Bohemond III and Thoros II, Prince of Armenia (r. 1144–1169), because they were the Byzantine emperor's vassals; Raymond, however, remained imprisoned.[31]

Bertrand de Blanchefort, Grand Master of the Knights Templar, reminded Louis VII of France (r. 1137–1180) in November 1164 that Amalric would be unable to defend the crusader states alone.[32] Nur ad-Din captured the fortress at al-Munaytira in 1165 (or 1166), and destroyed the Templars' castles at Halba, Araima and Safita in the summer of 1167.[32] According to Kevin James Lewis, Nur ad-Din captured Gibelacar during the latter campaign; the fortress was recaptured in late 1169 or early 1170.[33]

The date and the circumstances of Raymond's release are uncertain.[34][35] According to William of Tyre, Raymond was set free after spending eight solar years in captivity; however, Ibn Jubayr said that Raymond had been imprisoned for twelve lunar years.[35] Ali ibn al-Athir incorrectly recorded that Raymond was released after Nur ad-Din died on 15 May 1174,[36] but Raymond had witnessed a royal charter in Jerusalem on 18 April of that year.[35] Lewis writes that Raymond was released because of developing conflict between Nur ad-Din and his ambitious commander, Saladin, who was Egypt's actual ruler (r. 1169–1193).[37] The ailing Nur ad-Din (or his advisors) most probably regarded the crusader states as a buffer between his Syrian realm and Saladin's Egypt.[38]

William of Tyre reported that Raymond had to pay 80,000 pieces of gold as ransom, but could only pay 20,000.[39] To guarantee payment of the arrears, Raymond surrendered hostages.[38] Muslim authors wrote that Raymond's ransom amounted to 150,000 Syrian dinars.[40] According to a charter of Bohemond III of Antioch, Raymond borrowed money from the Knights Hospitaller to pay at least part of his ransom.[40]

Walter of Saint Omer, Prince of Galilee, died in early 1174.[41][42] Amalric of Jerusalem gave Walter's widow Eschiva of Bures in marriage to Raymond, enabling him to seize a large fief in the kingdom.[41][42] Their marriage was childless, according to William of Tyre, but Raymond loved his wife and brought up her children by her first husband as if they were his own.[43] King Amalric died on 11 July 1174.[44] His only son Baldwin was crowned king four days later, although he was a minor and had lepromatous leprosy.[45][46] The seneschal Miles of Plancy took charge of the government,[46] but was unable to persuade the commanders of the army to cooperate with him.[47]

Taking advantage of the seneschal's unpopularity, Raymond visited the king at Jerusalem in August and laid claim to the regency.[48][42] He argued that he was the closest male relative and the most powerful vassal of the child king.[49][50] Raymond also emphasized that since he had appointed the king's father to administer Tripoli during his captivity, he was entitled to claim the same treatment.[49] Miles of Plancy postponed the decision about Raymond's claim, saying that only the plenary session of the High Court of Jerusalem could hear it.[51]

Raymond returned to Tripoli,[52] and Miles of Plancy was murdered in Acre in October 1174.[46] The most powerful noblemen and clergymen assembled in Jerusalem to decide on the administration of the kingdom,[46][53] and the bishops unanimously supported Raymond's claim to regency.[44][52] The constable Humphrey II of Toron, Reginald of Sidon, and the Ibelin brothers Baldwin and Balian also stood by him, but Raymond was elected bailiff (or regent) only after a two-day debate, most probably because other aristocrats distrusted him.[53][52] Raymond was installed at the Church of the Holy Sepulchre, the traditional venue for royal coronations, in an extravagant ceremony.[54] He allowed the king's mother Agnes of Courtenay to return to the royal court, enabling her to strengthen her influence on the young monarch.[55] Raymond made the erudite William of Tyre chancellor, but left the office of seneschal vacant.[56]

Ruins of the crusader castle at Arqa

Saladin had expanded his rule to Damascus, Baalbek, Shaizar and Hama, taking advantage of the minority of Nur ad-Din's son As-Salih Ismail al-Malik.[57][58] He occupied Homs in early December 1174, but the garrison at the citadel resisted.[46] Without forcing the garrison to surrender, Saladin left Homs for Aleppo (the seat of the Zengids in Syria)[58] and left a small army in Homs' lower town.[58]

Saladin's fierce determination to unite Egypt and Syria threatened the crusader states.[57] Raymond mustered the troops of Jerusalem and Tripoli at Arqa in early 1175, but did not intervene in the conflict between Saladin and the Zengids.[57][58] The defenders of the Homs citadel offered to set their Christian prisoners free if he provided military assistance for them;[57] the prisoners included the hostages held as a guarantee for the arrears of Raymond's ransom.[57] According to Ali ibn al-Athir, the Muslim burghers of Aleppo also urged Raymond to attack Saladin's troops.[57] Raymond was willing to assist the defenders of Homs only if they immediately released their prisoners, but they refused his demand.[58] William of Tyre later emphasized that the commanders of the crusader army doubted if the defenders of the Homs citadel actually wanted to release their prisoners.[59]

Saladin returned to Homs soon after he was informed about the negotiations between the crusaders and the garrison.[60] Instead of attacking him, the crusader army retreated to Krak des Chevaliers;[60] this enabled Saladin to capture the citadel on 17 March 1175.[61] He sent envoys to the crusaders' camp to secure their neutrality in his conflict with the Zengids.[60] After Saladin agreed to release the hostages who were surety for Raymond's ransom, the crusader army withdrew to Tripoli.[60] William of Tyre blamed Humphrey II of Toron for the crusaders' decision.[62]

Saladin defeated the united armies of Aleppo and Mosul in the Battle of the Horns of Hama on 13 April,[61] and concluded a peace treaty with Aleppo which consolidated his rule in South Syria.[60] After he allowed his Egyptian troops to return home, the crusader army was also disbanded in early May.[60] Raymond proposed a truce to Saladin, which was signed on 22 July.[61][62] The truce enabled Saladin to march through Oultrejordain—the easternmost territory of the Kingdom of Jerusalem—without resistance during his new campaign against Ghazi II Saif ud-Din of Mosul (r. 1170–1180) in the summer of 1176.[63]

Copper fals minted in Saladin's name

Baldwin IV came of age at his fifteenth birthday on 15 July 1176.[62] With the end of his regency, Raymond returned to Tripoli.[62] Count Philip I of Flanders (r. 1168–1191) landed at Acre at the head of a large army of crusaders from Europe on 1 August 1177.[64][65] The young king and his advisors made several efforts to persuade him to join a military campaign against Egypt, Saladin's principal power base, but Philip kept making excuses.[66] According to rumours spreading among the crusaders, Raymond and Bohemond III convinced the count to resist because, as William of Tyre recorded it, they wanted to "entice him to their own lands, hoping with his help to undertake something which would benefit their states".[67][68]

Philip came to Tripoli in late October.[69] Roger de Moulins, Grand Master of the Knights Hospitallers, and more than 100 knights and 2,000 foot soldiers from the Kingdom of Jerusalem joined them in November.[70][71] They attacked Hama, taking advantage of its governor's illness.[71] The siege lasted only four days, because Bohemond persuaded them to join him in attacking Harenc.[72] They laid siege to the fortress in early December, but could not capture it.[73] Bohemond made peace with the Zengid ruler of Aleppo in early 1177.[73]

Raymond attacked a group of Turkmen and seized considerable booty from them in 1178 or 1179, but Saladin strengthened his border defence to prevent further raids.[74] Saladin also dispatched a group of horsemen to raid the Sidon region in early June 1179,[75] and Baldwin mustered his troops to prevent their retreat.[75][76] Raymond, who was staying at Tiberias, joined the royal army.[74] They routed the raiders at a ford on the Litani River, but Saladin suddenly marched into Galilee and defeated the crusaders in the Battle of Marj Ayyun on 10 June.[74][75][76] Although Raymond (who watched the battle from a hill) escaped to Tyre, his stepson Hugh of Saint Omer was captured.[74]

According to the Estoire de Eracles (which contains many folkloristic elements), Raymond pledged the first wealthy heiress in his county in marriage to the Flemish knight Gerard of Ridefort.[77][78] When William Dorel, Lord of Botrun (now Batroun in Lebanon) died—leaving a daughter as his heir—Raymond instead gave her to Plivain, a wealthy merchant from Pisa who had promised her weight in gold to him.[77][79] Raymond's perfidy outraged Ridefort, who left Tripoli and settled in the Kingdom of Jerusalem in 1179.[80]

Raymond and Bohemond III of Antioch ride to Jerusalem in early 1180.

Raymond and Bohemond III mustered their troops and marched to Jerusalem in April 1180.[81][82] Although they ostensiblly came to celebrate Easter in the Holy City, the ailing Baldwin IV feared that they wanted to depose him.[81][82] He hastily married his sister and heir presumptive, Sibylla, to Guy of Lusignan (a knight who had recently arrived from Poitou), although she had been promised to Duke Hugh III of Burgundy (r. 1162–1192).[83][84] After studying the controversial reports of the events, historian Bernard Hamilton concluded that Raymond and Bohemond wanted to stage a coup; they were concerned about the growing influence of the king's mother and her brother, Joscelin III of Edessa.[85] According to Hamilton, Raymond and Bohemond wanted to forcibly persuade the king to marry Sibylla to Baldwin of Ibelin (a local candidate of their choosing) instead of Hugh, who was related to the Courtenays; Sibylla's marriage to Guy, however, destroyed their plan.[85] Since Raymond and Bohemond had lost the king's favor, they left Jerusalem shortly after Easter.[86]

[T]he lord Prince Bohemond of Antioch and the lord Count Raymond of Tripoli, entering the kingdom with an army, terrified the lord king who feared lest they should attempt to organise a revolution by deposing the king and laying claim to the kingdom for themselves. For the king was afflicted more grievously than usual by his illness and day by day the symptoms of leprosy became more and more evident. The sister of the king ... was awaiting the arrival of [Hugh III of Burgundy] ... When the king knew that these noblemen had come, although both of them were his kinsmen, he viewed them with suspicion and hastened his sister's marriage. ... [B]ecause certain things had happened, she was unexpectedly married to a certain young man called Guy of Lusignan.

— William of Tyre: History of Deeds Done Beyond the Sea[87]

They were crossing Galilee when Saladin invaded the principality, and their arrival forced him to retreat.[81] Saladin and Baldwin signed a two-year truce.[81][88] The truce did not cover Tripoli, enabling Saladin to launch a sudden raid on the county.[86] Since the surprise attack prevented Raymond from mustering his troops, he fled to the fortress of Arqa.[81] Saladin's army pillaged the northern plains of the county, and his fleet captured the island of Ruad at Tortosa (now Arwad in Lebanon).[81] He withdrew his troops only after Raymond signed a truce.[89] Over the following years, Raymond strengthened the county's defence by granting new territories to the Knights Hospitaller or confirming his vassals' grants to them.[89]

After a two-year absence, Raymond decided to again visit Galilee in April 1182.[90] Agnes of Courtenay and Joscelin III persuaded Baldwin IV to forbid his entrance to the kingdom, however, forcing him to turn back at Beirut.[90][91] Before long, certain "princes and greater men of the realm" (whom William of Tyre failed to identify) convinced the king to allow Raymond to come to Jerusalem.[90][92] At the following general assembly, Raynald of Châtillon, Lord of Oultrejordain, proposed a military expedition across the Jordan River to prevent Saladin's march from Egypt to Syria in May 1182.[93] Although Raymond opposed Châtillon's plan because it would have left the western lands of the kingdom undefended during the campaign, Châtillon convinced most of the realm's barons to accept his proposal.[93]

The ancient water system at Saffuriya. The royal troops customarily assembled at the springs.[94]

Raymond accompanied the royal army to Oultrejordain.[90] During his absence, troops from the nearby Muslim towns invaded Galilee and captured 500 women.[95][96] The invaders also seized a fortified cave near Tiberias, with the assistance of the local Christian garrison.[95][97] The royal army returned to the kingdom's central territories, because Baldwin suspected that Saladin was planning further raids.[98] Raymond went to Tiberias, where he fell seriously ill.[96] When Saladin besieged the castle of Bethsain (now Beit She'an in Israel) on 13 July, Raymond dispatched his stepson Hugh to command the troops of Galilee[96] and join the royal army assembling near Saffuriya.[98] The royal army forced Saladin to lift the siege and withdraw his troops from the principality.[98]

Raymond made a plundering raid on the region of Bosra in late 1182.[96] According to Hamilton, it was "a reconnaissance expedition" because Bosra was an excellent location to study the southward movements of the Damascus army.[99] Kevin James Lewis writes that Raymond must have also participated in the king's unsuccessful campaign against Syria before Christmas, because the royal army had assembled at Tiberias.[94] Saladin seized Aleppo, the Zengids' last important stronghold in Syria, on 12 June 1183;[100] he soon decided to invade the kingdom and bring the crusaders to a pitched battle.[101][102] At Baldwin's order, more than 1,000 knights and about 15,000 foot soldiers gathered at Saffuriya;[101][102] Raymond also hurried to the mustering point.[94] Baldwin developed a fever, which forced him to appoint Guy of Lusignan bailiff.[103] Saladin crossed the Jordan and pillaged Bethsan on 29 September.[104] Although he continued his campaign for nine days, the crusaders refrained from attacking his troops.[105] William of Tyre reported that most common soldiers accused Guy's opponents of refusing to attack the invaders because they feared that a victory would strengthen Guy's position.[94]

Relations between Guy and the king became tense during the following months.[106][107] Baldwin summoned the realm's barons to an assembly to discuss the future of the kingdom's administration.[108] Raymond, Bohemond, Reginald of Sidon and the Ibelin brothers easily persuaded him to dismiss Guy.[94][109] They also convinced the king to make Guy's infant stepson, Baldwin of Montferrat, his heir,[94][109] and the child was crowned on 20 November 1183.[109] William of Tyre reported that it was "the general wish" that the king should also appoint a regent, and most of the barons said that only Raymond "was suited to hold this office".[110] The assembly was soon dissolved, because news about Saladin's sudden attack against Châtillon's Kerak Castle reached Jerusalem.[111] The king mustered an army, but could not personally participate in the campaign for long and appointed Raymond to command the army before it crossed the Jordan.[112] Learning about the arrival of the relief army, Saladin lifted the siege on 3 or 4 December.[112]

Baldwin IV appoints Raymond regent at his death bed, and the child Baldwin V's coronation

Heraclius (the Latin Patriarch of Jerusalem) and the grand masters of the Templars and Hospitallers tried to mediate a reconciliation between Baldwin IV and Guy of Lusignan, but the king did not forgive his brother-in-law.[112] In October 1184, Guy raided the Bedouin tribes who grazed their herds in the royal domain of Deir al-Balah.[94] This action enraged the king, who (according to William of Tyre) soon assembled the realm's barons and handed over "the government of the kingdom and its general administration" to Raymond.[94] However, Ernoul's chronicle and the Estoire de Eracles state that Baldwin IV decided to appoint a regent only after the members of the High Court had warned him that Guy (who was the minor Baldwin's stepfather) was still entitled to govern the kingdom after his death.[113] The dying king asked them to name their candidate, and they unanimously nominated Raymond.[114] According to Ernoul's chronicle, Baldwin IV accepted their choice and asked Raymond "to act as regent of the kingdom and of the child for ten years until the child came of age".[114] Although most sources failed to mention the date of these events, one version of the Estoire de Eracles states that Raymond was made regent in 1185.[115][116]

Ernoul and the Estoire de Eracles recorded that the High Court passed specific rules about the regency before Raymond was installed;[117] the barons chose Joscelin III as the child king's guardian.[117][118] The High Court also stipulated that the military orders would hold all royal fortresses during the king's minority, but Beirut was granted to Raymond to compensate him for the expenses of state administration.[117][118] The High Court also ruled that if the child king died before reaching the age of majority, the pope, the Holy Roman Emperor and the kings of France and England would be approached to decide whether his mother or her half-sister, Isabella, had the stronger claim to succeed him.[117][118] Although some versions of the Estoire de Eracles hint that Raymond persuaded the High Court to pass these rules, most of them were clearly adopted to limit the regent's authority.[117]

The date of Baldwin IV's death is unknown, but it is certain that he died before 16 May 1185.[118] The king was still alive when Raymond sent envoys to Saladin to begin negotiating an armistice.[119] Saladin granted a four-year truce, and a continuator of William of Tyre's chronicle wrote that "the land was free from external battles" during Raymond's second regency.[119] Saladin agreed to make peace with the crusaders because Izz ad-Din Mas'ud, the Zengid ruler of Mosul (r. 1180–1193), had formed a coalition against him.[120] He made a series of attacks against Mosul, forcing Izz ad-Din to accept his suzerainty in March 1186.[118][121] Raymond could not strengthen his authority during his regency;[122] Joscelin III of Edessa, Patriarch Heraclius and Peter, Archdeacon of Lydda (who had succeeded William of Tyre as chancellor) were Guy of Lusignan's supporters,[122] and the Knights Templar elected his enemy Gerard of Ridefort as their grand master.[122][77]

Baldwin V died unexpectedly in Acre during the summer of 1186.[118] Joscelin III convinced Raymond to go to Tiberias to make preparations for a general assembly and let the Templars deliver the young king's body to Jerusalem.[123][124] Taking advantage of Raymond's absence, Joscelin took control of Acre and seized Beirut.[124][125] Raymond summoned the barons to Nablus, the fief of Balian of Ibelin (one of his main supporters).[123][124] According to Arnold of Lübeck and Ali ibn al-Athir, Raymond tried to seize the throne at the assembly.[124] The reliability of their reports is questionable; neither was at the meeting, and they wrote their allegations years after the events.[124][126] The reports, however, are clear evidence of a "widespread belief" in Raymond's ambitions to seize the crown.[124][126]

While most of the barons were assembling at Nablus, Sibylla and Guy of Lusignan attended the king's funeral in Jerusalem.[124] The patriarch of Jerusalem, the grand masters of the Templars and Hospitallers, and Raynald of Châtillon were also present.[127][123] Staunch supporters of Sybilla, they decided to offer her the crown without waiting for the decision of the four Western monarchs (as the High Court had stipulated in early 1185).[127] Although she invited the barons at Nablus to attend her coronation, they did not acknowledge her right to rule, forbade the ceremony,[128][129] and sent two Cistercian abbots to Jerusalem to inform her of their veto.[130] Raymond dispatched one of his retainers to accompany the abbots in disguise, to spy in the capital.[130]

Ruins of the crusaders' castle in Tiberias

Sibylla's supporters ignored the barons' opposition, and Patriarch Heraclius crowned her before the end of September.[118] She soon put the crown on Guy's head, and the patriarch anointed him.[130][129] According to the Estoire de Eracles, Ridefort proudly declared "this crown well worth the marriage of Botrun" in reference to Raymond's betrayal.[130] Raymond and his supporters decided to elect Sibylla's half-sister Isabella and her husband, Humphrey IV of Toron, king when they learned about the coronation.[130] Humphrey—who was Châtillon's stepson—secretly left Nablus for Jerusalem and paid homage to Guy because he did not want to begin a civil war.[130] Most barons followed Humphrey's example, swearing fealty to the royal couple before the end of October.[130][131] After his former partisans abandoned him, Raymond returned to Tiberias without paying homage to Sibylla and Guy.[132]

Guy accused Raymond of betrayal, and invaded Galilee in October.[118][132] The king also demanded an accounting of Raymond's regency, but Raymond answered that he had spent all royal income on state administration.[133] Raymond decided to resist, and sought assistance from Saladin.[132] The sultan sent troops to Tiberias, forcing Guy to withdraw.[132][134] According to Ibn al-Athir, Saladin offered to make Raymond "an independent king for the Franks one and all".[135] Arnold of Lübeck also wrote that Raymond pledged to allow Saladin's army to invade the kingdom across Galilee in exchange for the sultan's assistance in seizing the throne.[136]

Lewis suggests that the Occitan troubadour Peire Vidal visited Raymond's court in Tiberias around the time of the conflict between Raymond and the royal couple.[137] Raymond provided patronage to Vidal, who dedicated a eulogy to him in one of his poems.[138] Lewis also says that it was around that time that Raymond offered to appoint a member of the House of Toulouse his heir if he was willing to settle in the County of Tripoli.[139] Since Raymond's offer is only recorded in a version of a late source, the Lignages d'Outremer, it may have been invented by its author.[139]

But upon Tripoli I rely
Because whereas the other barons
Chase away glory, he retains it
And does not let it depart from him

— Peire Vidal[138]

Saladin decided to launch a full-scale invasion against the kingdom, and began mustering forces from his whole empire in early 1187.[140] The barons convinced Guy to seek reconciliation with Raymond.[141] The masters of the two military orders, Joscius, Archbishop of Tyre, Raynald of Sidon and Balian of Ibelin, were appointed to begin negotiations with Raymond in Tiberias.[140][141] Saladin's son, Al-Afdal, sent Muzaffar al-Din, lord of Harenc and Edessa, to raid the kingdom.[142] In accordance with his treaty with Saladin, Raymond allowed the Syrian troops free entry into Galilee.[143] After Al-Afdal began raiding the Nazareth region, the masters of the military orders (Gerard of Ridefort and Roger des Moulins) attacked the invaders; the enemy forces, however, seriously outnumbered their retinue.[144] The raiders almost annihilated the crusaders at the springs of Cresson on 1 May;[143] only Ridefort and three knights escaped the battlefield.[143] The Estoire de Eracles blamed Ridefort for the catastrophe, emphasizing that Raymond's envoys had warned him not to attack the large Syrian army.[144] The invaders rode back to Syria across Galilee, displaying the severed heads of crusaders killed in battle on the points of their lances.[144]

Balian of Ibelin and the archbishops of Tyre and Nazareth arrived at Tiberias the following day.[144][145] Ernoul—who was present, as Ibelin's squire—wrote that the news of the crusaders' catastrophe came as a shock to Raymond,[146] and he soon agreed to pay homage to Guy.[146] He also expelled the Muslim garrison which had been stationed in Tiberias since his alliance with Saladin.[147] According to Ali ibn al-Athir, Raymond agreed to come to terms with the king only after his vassals threatened him with disobedience, and the prelates announced that they were ready to excommunicate him and annul his marriage.[144][148] Raymond and the king met near Jerusalem, at Fort St Job, which was held by the Hospitallers.[149] After they dismounted, Raymond knelt to the king in homage.[149] According to Ernoul, Guy soon lifted him up[149] and expressed regret for his irregular coronation.[146]

The king ordered the assembly of the kingdom's troops at Saffuriya.[141][150] Raymond joined the royal army with all the knights from Galilee, leaving his wife in Tiberias at the head of a small garrison.[151] Knights from the County of Tiberias also came to Saffuriya.[152] On 2 July 1187, Saladin invaded Galilee and besieged the town.[153] His troops outnumbered the crusaders' by over 30 percent.[147] Eschiva sent messengers to the crusaders' camp to inform them of Saladin's attack.[151]

The news about the siege of Tiberias aroused fresh conflict among the crusaders, because Raymond and Ridefort proposed opposite strategies.[151] Emphasizing that the town could resist even a prolonged siege, Raymond wanted to avoid a pitched battle[151] and proposed that Guy send envoys to Antioch asking Bohemond III for reinforcements.[154] Ridefort and Châtillon accused him of cowardice, adding that passivity would cost the king his kingdom.[154][151] Since the king was obviously willing to accept Raymond's proposal, Ridefort reminded him of Raymond's previous alliance with Saladin.[154][151] The king finally decided to attack, and ordered his army to march towards Tiberias.[154]

As lord of the region, Raymond was appointed to guide the army across Galilee.[155][156] After Saladin's troops began attacking the rear held by the Templars, the crusaders halted at Maskana; however, the local well could not provide enough water for a large army.[155][156] Ernoul blamed Raymond for this decision, but the anonymous author of the Libellus de expugnatione Terrae Sanctae per Saladinum—who also participated in the campaign—wrote that the king decided to stop against Raymond's advice.[157] Saladin's troops encircled the crusaders' camp and killed all crusaders who left it in search of water.[158] The army continued marching towards Tiberias the following day, with Raymond commanding the vanguard and Saladin's troops attacking them.[159][160] A group of thirsty foot soldiers which tried to break through enemy lines towards the distant Sea of Galilee was massacred,[160] and five of Raymond's knights defected to Saladin's side.[160] Raymond led a cavalry charge against the right wing of Saladin's army in an attempt to reach the springs near Hattin, forcing the Muslim troops to open a pass without resistance.[161] Instead of turning back, Raymond and the crusaders who had accompanied him (including Reynald of Sidon, Balian of Ibelin and Joscelin III of Edessa) hurried to Safed and then to Tyre.[161][162]

The rest of the crusader army was annihilated;[150][163] Raymond's many vassals—Plivain of Botrun, Hugh II Embriaco and Melioret of Maraqiyya—were captured.[162] The towns of the kingdom, left nearly defenseless, could not resist, and Saladin captured almost all of them over the following month.[164] Eschiva of Bures surrendered Tiberias to Saladin, and joined Raymond in Tyre;[165] Embriaco surrendered his fief of Jubayl to Saladin in exchange for his release on 4 August.[162] After Saladin occupied Beirut on 6 August, Raymond fled to Tripoli because he thought that Saladin could also easily capture Tyre.[166] His old allies, Balian of Ibelin and Raynald of Sidon, soon joined him.[165]

Raymond fell seriously ill in Tripoli,[167] and Baha ad-Din ibn Shaddad recorded that he had pleurisy.[167][168] Other sources—Ernoul, the Estoire de Eracles and Abu'l-Fida—emphasized that Raymond's sorrow for the crusaders' catastrophic defeat at Hattin caused his illness.[168] The childless Raymond willed the County of Tripoli to the eldest son of Bohemond III of Antioch, Raymond, who was his godson.[168] The contemporaneous Ralph of Diceto recorded that Raymond died fifteen days after the fall of Jerusalem, on 17 October 1187.[169] However, Lewis proposes that Raymond probably died in September.[170]