Ayyubid Dynasty

The progenitor of the Ayyubid dynasty, Najm ad-Din Ayyub ibn Shadhi, belonged to the Kurdish Rawadiya tribe, itself a branch of the large Hadhabani tribe. Ayyub's ancestors settled in the town of Dvin, in northern Armenia. When Turkish generals seized the town from its Kurdish prince, Shadhi left with his two sons Ayyub and Asad ad-Din Shirkuh.

Imad ad-Din Zangi, the ruler of Mosul, was defeated by the Abbasids under Caliph al-Mustarshid and Bihruz. Ayyub provided Zangi and his companions boats to cross the Tigris River and safely reach Mosul. As a consequence, Zangi recruited the two brothers into his service. Ayyub was made commander of Ba'albek and Shirkuh entered the service of Zangi's son, Nur ad-Din. According to historian Abdul Ali, it was under the care and patronage of Zangi that the Ayyubid family rose to prominence.

Nur al-Din had long sought to intervene in Egypt especially after missing his opportunity when Tala ibn Ruzzik successfully brought the country under control, blocking his ambitions for nearly a decade. Thus, Nur al-Din closely watched the events of 1163 with his reliable general Shirkuh waiting for an appropriate opportunity to bring the country under his control.

In 1164, Nur al-Din dispatched Shirkuh to lead an expeditionary force to prevent the Crusaders from establishing a strong presence in an increasingly anarchic Egypt. Shirkuh enlisted Ayyub's son, Saladin, as an officer under his command. They successfully drove out Dirgham, the vizier of Egypt, and reinstated his predecessor Shawar. After being reinstated, Shawar ordered Shirkuh to withdraw his forces from Egypt, but Shirkuh refused, claiming it was Nur al-Din's will that he remain. Over the course of several years, Shirkuh and Saladin defeated the combined forces of the Crusaders and Shawar's troops, first at Bilbais, then at a site near Giza, and in Alexandria, where Saladin would stay to protect while Shirkuh pursued Crusader forces in Lower Egypt.

When Shirkuh, now vizier of Egypt, dies, the Shi'ite Fatimid caliph al-Adid instates Saladin as the new vizier. He hopes Saladin will be easily influenced due to his lack of experience. Saladin consolidated his control in Egypt after ordering Turan-Shah to put down a revolt in Cairo staged by the Fatimid army's 50,000-strong Nubian regiments.

After this success, Saladin began granting his family members high-ranking positions in the country and increased Sunni Muslim influence in Shia Muslim-dominated Cairo

When caliph al-Adid dies, Saladin takes advantage of the power vacuum to seize greater control. He proclaims the return of Sunni Islam to Egypt, and the Ayyubid dynasty, named after Saladin's father Ayyub, begins. Saladin remains loyal to Zengid sultan Nur al-Din only in name.

In late 1172, Aswan was besieged by former Fatimid soldiers from Nubia and the governor of the city, Kanz al-Dawla—a former Fatimid loyalist—requested reinforcements from Saladin who complied. The reinforcements had come after the Nubians had already departed Aswan, but Ayyubid forces led by Turan-Shah advanced and conquered northern Nubia after capturing the town of Ibrim.

From Ibrim, they raided the surrounding region, halting their operations after being presented with an armistice proposal from the Dongola-based Nubian king. Although Turan-Shah's initial response was hawkish, he later sent an envoy to Dongola, who upon returning, described the poverty of the city and of Nubia in general to Turan-Shah. Consequently, the Ayyubids, like their Fatimid predecessors, were discouraged from further southward expansion into Nubia due to the poverty of the region, but required Nubia to guarantee the protection of Aswan and Upper Egypt.

In 1174, Sharaf al-Din Qaraqush, a commander under al-Muzaffar Umar, conquered Tripoli from the Normans with an army of Turks and Bedouins. Subsequently, while some Ayyubid forces fought the Crusaders in the Levant, another of their armies, under Sharaf al-Din, wrested control of Kairouan from the Almohads in 1188.

Saladin sent Turan-Shah to conquer Yemen and the Hejaz. Aden became the principal maritime port of the dynasty in the Indian Ocean and the principal city of Yemen. The advent of the Ayyubids marked the beginning of a period of renewed prosperity in the city which saw the improvement of its commercial infrastructure, the establishment of new institutions, and the minting of its own coins. Following this prosperity, the Ayyubids implemented a new tax which was collected by galleys.

Turan-Shah drove out the remaining Hamdanid rulers of Sana'a, conquering the mountainous city in 1175. With the conquest of Yemen, the Ayyubids developed a coastal fleet, al-asakir al-bahriyya, which they used to guard the sea coasts under their control and protect them from pirate raids. The conquest held great significance for Yemen because the Ayyubids managed to unite the previous three independent states (Zabid, Aden, and Sana'a) under a single power.

From Yemen, as from Egypt, the Ayyubids aimed to dominate the Red Sea trade routes which Egypt depended on and so sought to tighten their grip over the Hejaz, where an important trade stop, Yanbu, was located. To favor trade in the direction of the Red Sea, the Ayyubids built facilities along the Red Sea-Indian Ocean trade routes to accompany merchants. The Ayyubids also aspired to back their claims of legitimacy within the Caliphate by having sovereignty over the Islamic holy cities of Mecca and Medina. The conquests and economic advancements undertaken by Saladin effectively established Egypt's hegemony in the region.

After Nur al-Din's death in 1174. Thereafter, Saladin set out to conquer Syria from the Zengids, and on November 23 he was welcomed in Damascus by the governor of the city. By 1175, he had taken control of Hama and Homs, but failed to take Aleppo after besieging it. Saladin's successes alarmed Emir Saif al-Din of Mosul, the head of the Zengids at the time, who regarded Syria as his family's estate and was angered that it was being usurped by a former servant of Nur al-Din. He mustered an army to confront Saladin near Hama.

The Battle of the Horns of Hama was an Ayyubid victory over the Zengids, which left Saladin in control of Damascus, Baalbek, and Homs. Although heavily outnumbered, Saladin and his veteran soldiers decisively defeated the Zengids.

Gökböri commanded the right wing of the Zengid army, which broke Saladin's left flank before being routed by a charge from Saladin's personal guard. Despite around 20,000 men being involved on both sides, Saladin gained a nearly-bloodless victory by the psychological effect of the arrival of his Egyptian reinforcements. The Abbasid caliph, al-Mustadi, graciously welcomed Saladin's assumption of power and gave him the title of "Sultan of Egypt and Syria".

On 6 May 1175, Saladin's opponents agreed to a treaty recognizing his rule over Syria apart from Aleppo. Saladin requested that the Abbasid caliph acknowledge his right to the entirety of Nur ad-Din's empire, but he was recognized simply as lord over what he already held and was encouraged to attack the Crusaders in Jerusalem.

Saladin had by now agreed truces with his Zengid rivals and the Kingdom of Jerusalem (the latter occurred in the summer of 1175), but faced a threat from the Isma'ili sect known as the Assassins, led by Rashid ad-Din Sinan. Based in the an-Nusayriyah Mountains, they commanded nine fortresses, all built on high elevations. As soon as he dispatched the bulk of his troops to Egypt, Saladin led his army into the an-Nusayriyah range in August 1176. He retreated the same month, after laying waste to the countryside, but failing to conquer any of the forts. Most Muslim historians claim that Saladin's uncle, the governor of Hama, mediated a peace agreement between him and Sinan.

Saladin had his guards supplied with link lights and had chalk and cinders strewed around his tent outside Masyaf—which he was besieging—to detect any footsteps by the Assassins. According to this version, one night Saladin's guards noticed a spark glowing down the hill of Masyaf and then vanishing among the Ayyubid tents. Presently, Saladin awoke to find a figure leaving the tent. He saw that the lamps were displaced and beside his bed laid hot scones of the shape peculiar to the Assassins with a note at the top pinned by a poisoned dagger. The note threatened that he would be killed if he did not withdraw from his assault. Saladin gave a loud cry, exclaiming that Sinan himself was the figure that had left the tent.

Viewing the expulsion of the Crusaders as a mutual benefit and priority, Saladin and Sinan maintained cooperative relations afterward, the latter dispatching contingents of his forces to bolster Saladin's army in a number of decisive subsequent battlefronts.

Philip I, Count of Flanders joined Raymond of Tripoli's expedition to attack the Saracen stronghold of Hama in northern Syria. A large crusader army, the Knights Hospitaller and many Templar knights followed him. This left the Kingdom of Jerusalem with very few troops to defend its various territories. Meanwhile, Saladin was planning his own invasion of the Kingdom of Jerusalem from Egypt. When he was informed of the expedition north, he wasted no time in organising a raid and invaded the kingdom with an army of some 30,000 men. Learning of Saladin's plans, Baldwin IV left Jerusalem with, according to William of Tyre, only 375 knights to attempt a defense at Ascalon.

Saladin continued his march towards Jerusalem, thinking that Baldwin would not dare to follow him with so few men. He attacked Ramla, Lydda and Arsuf, but because Baldwin was supposedly not a danger, he allowed his army to be spread out over a large area, pillaging and foraging. However, unknown to Saladin, the forces he had left to subdue the King had been insufficient and now both Baldwin and the Templars were marching to intercept him before he reached Jerusalem. The Christians, led by the King, pursued the Muslims along the coast, finally catching their enemies at Mons Gisardi, near Ramla.

The 16-year-old Baldwin IV of Jerusalem, seriously afflicted by leprosy, led an outnumbered Christian force against Saladin's troops in what became one of the most notable engagements of the Crusades. The Muslim army was quickly routed and pursued for twelve miles. Saladin fled back to Cairo, reaching the city on 8 December, with only a tenth of his army.

In 1179, Saladin again invaded the Crusader states, from the direction of Damascus. He based his army at Banias and sent raiding forces to despoil villages and crops near Sidon and the coastal areas. Farmers and townspeople impoverished by Saracen raiders would be unable to pay rent to their Frankish overlords. Unless stopped, Saladin's destructive policy would weaken the Crusader kingdom.

In response, Baldwin moved his army to Tiberias on the Sea of Galilee. From there he marched north-northwest to the stronghold of Safed. Together with the Knights Templar led by Odo of St Amand and a force from the County of Tripoli led by Count Raymond III, Baldwin moved northeast.

The battle ended in a decisive victory for the Muslims and is considered the first in the long series of Islamic victories under Saladin against the Christians. The Christian king, Baldwin IV, who was crippled by leprosy, narrowly escaped being captured in the rout.

Between October 1178 and April 1179, Baldwin began the first stages of constructing his new line of defense, a fortification called Chastellet at Jacob's Ford. While construction was in progress, Saladin became fully aware of the task he would have to overcome at Jacob's Ford if he were to protect Syria and conquer Jerusalem. At the time, he was unable to stop the erection of Chastellet by military force because a large portion of his troops were stationed in northern Syria, putting down Muslim rebellions. By the summer of 1179, Baldwin's forces had constructed a stone wall of massive proportions.

Saladin summoned a large Muslim army to march southeast towards Jacob’s Ford. On 23 August 1179, Saladin arrived at Jacob’s Ford and ordered his troops to shoot arrows at the castle, thus initiating the siege. Saladin and his troops entered Chastellet. By 30 August 1179, the Muslim invaders had pillaged the castle at Jacob's Ford and killed most of its residents. On the same day, less than one week after reinforcements were called, Baldwin and his supporting army set out from Tiberias, only to discover smoke permeating the horizon directly above Chastellet. Obviously, they were too late to save the 700 knights, architects, and construction workers who were killed and the other 800 who were taken captive.

In 1180, Saladin arranged a truce between himself and two Christian leaders, King Baldwin and Raymond III of Tripoli to prevent bloodshed. But two years later, the lord of the Transjordan fief of Kerak, Reynald of Châtillon, ruthlessly attacked Muslim caravans passing through his lands on their way for pilgrimage, breaking pacts for the safe passage of pilgrims. Resenting this violation of the truce, Saladin immediately assembled his army and prepared to strike, devastating the enemy.

On 11 May 1182 Saladin left Egypt and led his army north toward Damascus via Ayla on the Red Sea. In the vicinity of Belvoir castle, the Ayyubid army confronted the Crusaders. Saladin's soldiers tried to disrupt the Crusader formation by raining arrows from their horse archers, by partial attacks and by feigned retreats. On this occasion, the Franks could neither be tempted into fighting a pitched battle nor stopped. Unable to make an impression on the Latin host, Saladin broke off the running battle and returned to Damascus.

In May 1182, Saladin captured Aleppo after a brief siege; the new governor of the city, Imad al-Din Zangi II, had been unpopular with his subjects and surrendered Aleppo after Saladin agreed to restore Zangi II's previous control over Sinjar, Raqqa, and Nusaybin, which would thereafter serve as vassal territories of the Ayyubids. Aleppo formally entered Ayyubid hands on 12 June. The day after, Saladin marched to Harim, near the Crusader-held Antioch and captured the city. The surrender of Aleppo and Saladin's allegiance with Zangi II had left Izz al-Din al-Mas'ud of Mosul the only major Muslim rival of the Ayyubids. Mosul had been subjected to a short siege in the autumn of 1182, but after mediation by the Abbasid caliph an-Nasir, Saladin withdrew his forces.

By September 1183, Baldwin, crippled by leprosy, could no longer function as monarch. Guy of Lusignan, who had married Baldwin's sister Sibylla of Jerusalem in 1180, was appointed regent.

On August 24, 1183, Saladin returned to Damascus, having conquered Aleppo and several cities in Mesopotamia for his empire. Crossing the Jordan River, the Ayyubid host plundered the abandoned town of Baisan. Continuing west, up the Jezreel Valley, Saladin established his army near some springs about 8 km southeast of al-Fule. At the same time, the Muslim leader sent out numerous columns to damage as much property as possible. The raiders destroyed the villages of Jenin and Afrabala, attacked the monastery on Mount Tabor and wiped out a contingent from Kerak that was trying to join the Crusader field army.

Expecting an attack, Guy of Lusignan mustered the Crusader host at La Sephorie. When intelligence reports detected Saladin's invasion route, Guy marched the field army to the small castle of La Fève (al-Fule). His army was swollen by pilgrims and Italian sailors to a size of 1,300–1,500 knights, 1,500 turcopoles and over 15,000 infantry. This was said to be the largest Latin army assembled "within living memory." He skirmished with Saladin's Ayyubid army for more than a week in September and October 1183. The fighting ended on 6 October with Saladin being forced to withdraw.

Guy was harshly criticized by some for failing to fight a major battle when in command of such a large host. Others, mostly native barons such as Raymond III of Tripoli, supported his cautious strategy. They pointed out that Saladin's army was drawn up on rough ground, unsuitable for a Frankish heavy cavalry charge. Soon after this battle, Guy lost his position as regent.

Kerak was the stronghold of Raynald of Châtillon, Lord of Oultrejordain, 124 km south of Amman. Raynald raided caravans that were trading near the Kerak castle for years. Raynald’s most daring raid was an 1182 naval expedition down the Red Sea to Mecca and El Medina. He continuously plundered the Red Sea coast and threatened the routes of pilgrims to Mecca in spring 1183. He captured the town of Aqaba, giving him a base of operations against Islam's holiest city, Mecca. Saladin, a Sunni Muslim and the leader of the Muslim forces, decided that the Kerak castle would be an ideal target for a Muslim attack, especially due to it being a block on the route from Egypt to Damascus. In early December, Saladin got news that King Baldwin's army was on the way. Upon learning of this, he abandoned the siege and fled to Damascus.

Saladin launched an offensive against Reynald’s castle at Kerak in 1187, leaving his son al Melik al-Afdal as commander of a contingency at Re’sulma. In response to the encroaching threat, Guy assembled the High Court in Jerusalem. A delegation of Gerard of Ridefort, master of the Knights Templar; Roger de Moulins, master of the Knights Hospitaller; Balian of Ibelin, Josicus, Archbishop of Tyre; and Reginal Grenier, lord of Sidon, were selected to journey to Tiberias to make peace with Raymond.

Meanwhile, al-Afdal gathered a raiding party to pillage the land surrounding Acre, while Saladin besieged Kerak. al-Afdal dispatched Muzzafar ad-Din Gökböri, Emir of Edessa, to lead this expedition, accompanied by two ranking emirs, Qaymaz al-Najami and Dildirim al-Yarugi. Knowing that his troops were poised to enter Raymond’s territory, Saladin agreed that the raiding party would only pass-through Galilee en route to Acre, leaving Raymond’s lands untouched. In Frankish sources, this raiding party consisted of approximately 7000 forces; however, modern historians believe 700 forces is more accurate.

On the morning of 1 May, the Frankish army rode east from Nazareth and happened upon the Ayyubid raiding party at the springs of Cresson. The Frankish cavalry launched an initial offensive, catching the Ayyubid forces off guard. However, this separated the Frankish cavalry from the infantry. According to Ali ibn al-Althir, the ensuing melee was equally matched; however, the Ayyubid forces succeeded in routing the divided Frankish army. Only Gerard and a handful of knights escaped death, and the Ayyubids took an unknown number of captives. Gokbori’s troops proceeded to pillage the surrounding area before returning across Raymond’s territory.

The Battle of Hattin, fought on 4 July 1187 near Tiberias in present-day Israel, was a pivotal clash between the Crusader states of the Levant and the Ayyubid forces led by Sultan Saladin. Saladin's victory decisively shifted the balance of power in the Holy Land, leading to the Muslim recapture of Jerusalem and sparking the Third Crusade.

Background tensions in the Kingdom of Jerusalem heightened with the ascension of Guy of Lusignan in 1186, amidst a split between the "court faction," supporting Guy, and the "nobles' faction," backing Raymond III of Tripoli. Saladin, having unified the Muslim regions surrounding the Crusader states and advocating for jihad, seized on these internal divisions.

The immediate cause of the battle was the violation of a truce by Raynald of Châtillon, prompting Saladin's military response. In July, Saladin besieged Tiberias, provoking the Crusaders into a confrontation. Despite advice against it, Guy of Lusignan led the Crusader army from their stronghold to engage Saladin, falling into his strategic trap.

On 3 July, the Crusaders, hampered by thirst and harassment by Muslim forces, made a fateful decision to march towards the Springs of Kafr Hattin, directly into Saladin's hands. Surrounded and weakened, the Crusaders were decisively defeated the following day. The battle saw the capture of key Crusader leaders, including Guy of Lusignan, and the loss of the True Cross, a symbol of Christian morale.

The aftermath was catastrophic for the Crusader states: key territories and cities, including Jerusalem, fell to Saladin in the following months. The battle exposed the vulnerability of the Crusader states and led to the mobilization of the Third Crusade. However, despite subsequent military campaigns, the Crusader presence in the Holy Land was irreversibly weakened, culminating in the eventual decline of Crusader power in the region.

By mid-September, Saladin had taken Acre, Nablus, Jaffa, Toron, Sidon, Beirut, and Ascalon. The survivors of the battle and other refugees fled to Tyre, the only city able to hold out against Saladin, due to the fortuitous arrival of Conrad of Montferrat. In Tyre, Balian of Ibelin had asked Saladin for safe passage to Jerusalem to retrieve his wife Maria Komnene, Queen of Jerusalem and their family. Saladin granted his request, provided that Balian not take up arms against him and not remain in Jerusalem for more than one day; however, Balian broke this promise.

Balian found the situation in Jerusalem dire. The city was filled with refugees fleeing Saladin's conquests, with more arriving daily. There were fewer than fourteen knights in the whole city. He prepared for the inevitable siege by storing food and money. The armies of Syria and Egypt assembled under Saladin, and after conquering Acre, Jaffa, and Caesarea, though he unsuccessfully besieged Tyre, the sultan arrived outside Jerusalem on September 20.

At the end of September, Balian rode out with an envoy to meet with the sultan, offering surrender. Saladin told Balian that he had sworn to take the city by force, and would only accept an unconditional surrender. Balian threatened that the defenders would destroy the Muslim holy places, slaughter their own families and the 5000 Muslim slaves, and burn all the wealth and treasures of the Crusaders. In the end, an agreement was made.

After the disastrous Battle of Hattin, much of the Holy Land had been lost to Saladin, including Jerusalem. The remnants of the crusader army flocked to Tyre, which was one of the major cities still in Christian hands. Reginald of Sidon was in charge of Tyre and was in the process of negotiating its surrender with Saladin, but the arrival of Conrad and his soldiers prevented it. Reginald left the city to refortify his castle at Belfort, and Conrad became the leader of the army. He immediately began to repair the defenses of the city, and he cut a deep trench across the mole that joined the city to the shore, to prevent the enemy from approaching the city.

All of Saladin's attacks failed, and the siege dragged on, with occasional sallies by the defenders, led by a Spanish knight named Sancho Martin, better known as the "green knight" due to the colour of his arms. It became clear to Saladin that only by winning at sea could he take the city. He summoned a fleet of 10 galleys commanded by a North African sailor named Abd al-Salam al-Maghribi. The Muslim fleet had initial success in forcing the Christian galleys into the harbour, but through the night of 29–30 December, a Christian fleet of 17 galleys attacked 5 of the Muslim galleys, inflicting a decisive defeat and capturing them.

After these events, Saladin summoned his emirs for a conference, to discuss if they should retire or keep trying. The opinions were divided, but Saladin, seeing the state of his troops, decided to retire to Acre.

The siege of Safed (November–December 1188) was part of Saladin's invasion of the Kingdom of Jerusalem. The siege of the Templar-held castle began in early November 1188. Saladin was joined by his brother, Saphadin. Saladin employed a large number of trebuchets and extensive mines. He also maintained a very tight blockade. According to Bahāʾ al-Dīn, the conditions were rainy and muddy. At one point, Saladin specified the placement of five trebuchets, mandating that they be assembled and in place by the morning.

It was the exhaustion of their supplies and not the attacks on the walls that induced the Templar garrison to sue for peace on 30 November. On 6 December, the garrison walked out on terms. They went to Tyre, which Saladin had failed to capture in an earlier siege.

Pope Gregory VIII called for a The Third Crusade against the Muslims in early 1189. Frederick Barbarossa of the Holy Roman Empire, Philip Augustus of France, and Richard the Lionheart of England formed an alliance to reconquer Jerusalem following the capture of Jerusalem by the Ayyubid sultan Saladin in 1187.

In Tyre, Conrad of Montferrat had entrenched himself and had successfully resisted Saladin's assault at the end of 1187. The sultan then turned his attention to other tasks, but then tried to negotiate the surrender of the city by treaty, as in mid-1188 the first reinforcements from Europe arrived at Tyre by sea. Under the terms of the treaty, Saladin would, among other things, release King Guy, whom he had captured at Hattin. Guy urgently needed a firm base from which he could organize a counterattack on Saladin, and since he could not have Tyre, he directed his plans to Acre, 50 km (31 miles) to the south.;

Hattin had left the Kingdom of Jerusalem with few troops left to call upon. In such a scenario, Guy was totally dependent on aid from the plethora of small armies and fleets descending on the Levant from around Europe.

From 1189 to 1191, Acre was besieged by the Crusaders, and despite initial Muslim successes, it fell to Crusader forces. A massacre of 2,700 Muslim prisoners of war ensued, and the Crusaders then made plans to take Ascalon in the south.

Following the capture of Acre in 1191, Richard was aware that he needed to capture the port of Jaffa before making an attempt on Jerusalem, Richard began to march down the coast from Acre towards Jaffa in August. Saladin, whose main objective was to prevent the recapture of Jerusalem, mobilised his army to attempt to stop the Crusaders' advance.;

The battle occurred just outside the city of Arsuf, when Saladin met Richard's army as it was moving along the Mediterranean coast from Acre to Jaffa, following the capture of Acre. During their march from Acre, Saladin launched a series of harassing attacks on Richard's army, but the Christians successfully resisted these attempts to disrupt their cohesion. As the Crusaders crossed the plain to the north of Arsuf, Saladin committed the whole of his army to a pitched battle.

Once again the Crusader army maintained a defensive formation as it marched, with Richard awaiting for the ideal moment to mount a counterattack. However, after the Knights Hospitaller launched a charge at the Ayyubids, Richard was forced to commit his entire force to support the attack. After initial success, Richard was able to regroup his army and achieve victory. The battle resulted in Christian control of the central Palestinian coast, including the port of Jaffa.

Following his victory at Arsuf, Richard took Jaffa and established his new headquarters there. In November 1191 the Crusader army advanced inland towards Jerusalem. The poor weather, combined with the fear that if it besieged Jerusalem the Crusader army might be trapped by a relieving force, caused the decision to retreat back to the coast to be made.

In July 1192, Saladin's army suddenly attacked and captured Jaffa with thousands of men, but Saladin lost control of his army due to their anger for the massacre at Acre.

Richard subsequently gathered a small army, including a large contingent of Italian sailors, and hurried south. Richard's forces stormed Jaffa from their ships and the Ayyubids, who had been unprepared for a naval attack, were driven from the city. Richard freed those of the Crusader garrison who had been made prisoner, and these troops helped to reinforce the numbers of his army. Saladin's army still had numerical superiority, however, and they counter-attacked. Saladin intended a stealthy surprise attack at dawn, but his forces were discovered; he proceeded with his attack, but his men were lightly armoured and lost 700 men killed due to the missiles of the large numbers of Crusader crossbowmen. The battle to retake Jaffa ended in complete failure for Saladin, who was forced to retreat. This battle greatly strengthened the position of the coastal Crusader states.

Saladin was forced to finalize a treaty with Richard providing that Jerusalem would remain under Muslim control, while allowing unarmed Christian pilgrims and traders to visit the city. Ascalon, with its defences demolished, be returned to Saladin's control. Richard departed the Holy Land on 9 October 1192.

Saladin died of a fever on 4 March 1193 at Damascus not long after King Richard's departure, leading to fighting between branches of the Ayyubid dynasty, as he has given his heirs control of mostly independent sections of the empire. His two sons, controlling Damascus and Aleppo, fight for power, but ultimately Saladin's brother al-Adil becomes sultan.

An earthquake in Syria and upper Egypt causes the death of some 30,000 people and much more from subsequent famine and epidemics

By 1208 Kingdom of Georgia challenged Ayyubid rule in eastern Anatolia and besieged Khilat (possessions of al-Awhad). In response al-Adil assembled and personally led large Muslim army that included the emirs of Homs, Hama and Baalbek as well as contingents from other Ayyubid principalities to support al-Awhad. During the siege, Georgian general Ivane Mkhargrdzeli accidentally fell into the hands of the al-Awhad on the outskirts of Khilat and was released in 1210, only after the Georgians agreed to sign a Thirty Years' Truce. The truce ended the Georgian menace to Ayyubid Armenia, leaving the Lake Van region to the Ayyubids of Damascus.

After the failure of the Fourth Crusade, Innocent III again called for a crusade, and began organizing Crusading armies led by Andrew II of Hungary and Leopold VI of Austria, soon to be joined by John of Brienne. An initial campaign in late 1217 in Syria was inconclusive, and Andrew departed. A German army led by cleric Oliver of Paderborn, and a mixed army of Dutch, Flemish and Frisian soldiers led by William I of Holland, then joined the Crusade in Acre, with a goal of first conquering Egypt, viewed as the key to Jerusalem.;

At the beginning of the Fifth Crusade, it was agreed that a force would attempt to take Damietta, located at the mouth of the river Nile. The Crusaders then planned to use this city as a launching point for the southern portion of a pincer attack upon Jerusalem from Acre and Suez. Control over the area would also provide wealth to finance the continuation of the crusade, and reduce the threat from the Muslim fleet.

In March 1218, the Crusader ships of the Fifth Crusade set sail to the port of Acre. In late May, the forces assigned to besiege Damietta set sail. The first ships arrived on May 27, although the main leaders were delayed by storms and further preparations. The crusading force included groups of Knights Templar and Knights Hospitaller, fleets from Frisia and Italy, and troops amassed under numerous other military leaders.

The city, under the control of the Ayyubid sultan al-Kamil, was besieged in 1218 and taken by the Crusaders in 1219.

The battle of Mansurah was the final battle in the Fifth Crusade (1217–1221). It pitted the Crusader forces under papal legate Pelagius Galvani and John of Brienne, king of Jerusalem, against the Ayyubid forces of the sultan al-Kamil. The result was a decisive victory for the Egyptians and forced the surrender of the Crusaders and their departure from Egypt.

The masters of the military orders were dispatched to Damietta with the news of the surrender. It was not well-received, but the eventual happened on 8 September 1221. The Crusader ships departed and the sultan entered the city. The Fifth Crusade ended in 1221, having accomplished nothing. The Crusaders were unable to even gain the return of the True Cross. The Egyptians could not find it and the Crusaders left empty-handed.

The Sixth Crusade was a military expedition to recapture Jerusalem and the rest of the Holy Land. It began seven years after the failure of the Fifth Crusade and involved very little actual fighting. The diplomatic maneuvering of the Holy Roman Emperor and King of Sicily, Frederick II, resulted in the Kingdom of Jerusalem regaining some control over Jerusalem for much of the ensuing fifteen years as well as over other areas of the Holy Land.

Frederick's army was not large. He could neither afford nor mount a lengthening campaign in the Holy Land. The Sixth Crusade would be one of negotiation. Frederick hoped that a token show of force, a threatening march down the coast, would be enough to convince al-Kamil to honor a proposed agreement that had been negotiated some years earlier. Al-Kamil was occupied with a siege in Damascus against his nephew an-Nasir Da’ud. He then agreed to cede Jerusalem to the Franks, along with a narrow corridor to the coast.

The treaty was concluded on 18 February 1229, and also involved a ten-year truce. In it, al-Kamil surrendered Jerusalem with the exception of some Muslim holy sites. Frederick also received Bethlehem and Nazareth, part of Sidon district, and Jaffa and Toron, dominating the coast. Frederick entered Jerusalem on 17 March 1229 and received the formal surrender of the city by al-Kamil's agent.

The siege of Damascus of 1229 was part of an Ayyubid succession war over Damascus that broke out following the death of al-Muʿaẓẓam I in 1227. The late ruler's son, al-Nāṣir Dāʾūd, took de facto control of the city in opposition to al-Kāmil, the Ayyubid sultan in Egypt. In the ensuing war, al-Nāṣir lost Damascus but preserved his autonomy, ruling from al-Karak.

Jalal ad-Din was the last ruler of the Khwarezm Shahs. Actually the territory of the sultanate had been annexed by the Mongol Empire during the reign of Jalal ad-Din’s father Alaaddin Muhammad; but Jalal ad-Din continued to fight with a small army. In 1225, he retreated to Azerbaijan and founded a principality around Maragheh, East Azerbaijan. Although initially he formed an alliance with the Seljuk Sultanate of Rûm against the Mongols, for reasons unknown he later changed his mind and began hostilities against the Seljuks. In 1230, he conquered Ahlat, (in what is now Bitlis Province, Turkey) an important cultural city of the era from the Ayyubids which led to an alliance between the Seljuks and Ayyubids. Jalal ad-Din on the other hand allied himself with Jahan Shah, the rebellious Seljuk governor of Erzurum.

During the first day, the alliance seized some positions from the Khwarezmians but the occupiers abandoned the newly captured positions at night. Jalal al-Din refrained from attacking. The alliance again started an attack on the next dawn but they were repelled back. After repelling the allied army, the Khwarezmians charged forward and forced Kaykubad I to retreat further. The lost positions were captured back. Al-Ashraf ,the commader of the Mamluk army reinforced Kaykubad's divisions. After seeing the reinforcements, Jalal al-Din concluded that the battle is lost, due to the numerical superiority of the alliance and abandoned the battlefield.

This battle was Jalal ad-Din’s last battle, as he lost his army, and while escaping in disguise he was spotted and killed in 1231. His short-lived principality was conquered by the Mongols.

Emperor Frederick II of the Holy Roman Empire led the Sixth Crusade from 1228 to 1229 and claimed the title of King of Jerusalem as the husband of Isabella II of Jerusalem, queen since 1212. However, Jerusalem did not remain in the hands of Christians for long, as the latter did not control the surroundings of the city sufficiently to be able to ensure an effective defense.

In 1244, the Ayyubids allowed the Khwarazmians, whose empire had been destroyed by the Mongols in 1231, to attack the city. The siege took place on 15 July, and the city fell rapidly. The Khwarazmians plundered it and left it in such a state of ruin that it became unusable for both Christians and Muslims. The sack of the city and the massacre which accompanied it encouraged the king of France Louis IX to organize the Seventh Crusade.

Various off-shoot families of the Ayyubids ally with the Crusaders against Ayyubid Sultan as-Salih Ayyub, but he is able to defeat them at the Battle of La Forbie. The Kingdom of Jerusalem collapses and he begins to consolidate power over the various Ayyubid factions.

The resulting Ayyubid victory led to the call for the Seventh Crusade and marked the collapse of Christian power in the Holy Land.

By the mid-13th century, the Crusaders became convinced that Egypt, the heart of Islam's forces and arsenal, was an obstacle to their ambition to capture Jerusalem, which they had lost for the second time in 1244. In 1245, during the First Council of Lyon, Pope Innocent IV gave his full support to the Seventh Crusade being prepared by Louis IX, King of France. The goals of the Seventh Crusade were to destroy the Ayyubid dynasty in Egypt and Syria, and to recapture Jerusalem.

The ships of the Seventh Crusade, led by King Louis's brothers, Charles d'Anjou and Robert d'Artois, sailed from Aigues-Mortes and Marseille to Cyprus during the autumn of 1248, and then on to Egypt. The ships entered Egyptian waters and the troops of the Seventh Crusade disembarked at Damietta in June 1249.

Emir Fakhr ad-Din Yusuf, the commander of the Ayyubid garrison in Damietta, retreated to the camp of the Sultan in Ashmum-Tanah, causing a great panic among the inhabitants of Damietta, who fled the town, leaving the bridge that connected the west bank of the Nile with Damietta intact. The Crusaders crossed over the bridge and occupied Damietta, which was deserted. The Crusaders were encouraged by the news of the death of the Ayyubid Sultan, as-Salih Ayyub. The Crusaders began their march towards Cairo.

Early on the morning of February 11, the Muslim forces launched an offensive against the Frankish army, with Greek Fire, but were repulsed with heavy losses, ending in a Frankish victory.

On 27 February Turanshah, the new Sultan, arrived in Egypt from Hasankeyf and went straight to Al Mansurah to lead the Egyptian army. Ships were transported overland and dropped in the Nile (in Bahr al-Mahala) behind the ships of the crusaders cutting the reinforcement line from Damietta and besieging the crusade force of King Louis IX. The Egyptians used Greek fire and destroyed and seized many ships and supply vessels. Soon the besieged crusaders were suffering from devastating attacks, famine and disease. Some crusaders lost faith and deserted to the Muslim side.

King Louis IX proposed to the Egyptians the surrender of Damietta in exchange for Jerusalem and some towns on the Syrian coast. The Egyptians, aware of the miserable situation of the crusaders, refused the besieged king's offer. On 5 April covered by the darkness of night, the crusaders evacuated their camp and began to flee northward towards Damietta. In their panic and haste they neglected to destroy a pontoon bridge they had set over the canal. The Egyptians crossed the canal over the bridge and followed them to Fariskur where the Egyptians utterly destroyed the crusaders on 6 April. Thousands of crusaders were killed or taken prisoner. Louis IX surrendered with his two brothers Charles d'Anjou and Alphonse de Poitiers. King Louis' coif was exhibited in Syria.

Al-Mu'azzam Turan-Shah alienated the Mamluks soon after their victory at Mansurah and constantly threatened them and Shajar al-Durr. Fearing for their positions of power, the Bahri Mamluks revolted against the sultan and killed him in April 1250. Aybak married Shajar al-Durr and subsequently took over the government in Egypt in the name of;al-Ashraf II;who became sultan, but only nominally.

In December 1250, An-Nasir Yusuf attacked Egypt after hearing of al-Mu'azzam Turan-Shah's death and the ascension of Shajar al-Durr. An-Nasir Yusuf's army was much larger and better-equipped than that of the Egyptian army, consisting of the forces of Aleppo, Homs, Hama, and those of Saladin's only surviving sons, Nusrat ad-Din and Turan-Shah ibn Salah ad-Din. Nonetheless, it suffered a major defeat at the hands of Aybak's forces. An-Nasir Yusuf subsequently returned to Syria, which was slowly slipping out of his control.

The Mamluks forged an alliance with the Crusaders in March 1252 and agreed to jointly launch a campaign against an-Nasir Yusuf. King Louis, who had been released after al-Mu'azzam Turan-Shah's murder, led his army to Jaffa, while Aybak intended to send his forces to Gaza. Upon hearing of the alliance, an-Nasir Yusuf immediately dispatched a force to Tell al-Ajjul, just outside Gaza, in order to prevent the junction of the Mamluk and Crusader armies.;

Realizing that a war between them would greatly benefit the Crusaders, Aybak and an-Nasir Yusuf accepted Abbasid mediation via Najm ad-Din al-Badhirai. In April 1253, a treaty was signed whereby the Mamluks would retain control over all of Egypt and Palestine up to, but not including, Nablus, while an-Nasir Yusuf would be confirmed as the ruler of Muslim Syria. Thus, Ayyubid rule was officially ended in Egypt.

The Mongol Great Khan, Möngke, issued a directive to his brother Hulagu to extend the realms of the empire to the Nile River. The latter raised an army of 120,000 and in 1258, sacked Baghdad and slaughtered its inhabitants, including Caliph al-Musta'sim and most of his family. An-Nasir Yusuf sent a delegation to Hulagu afterward, repeating his protestations to submission. Hulagu refused to accept the terms and so an-Nasir Yusuf called on Cairo for aid. Aleppo was soon besieged within a week and in January 1260 it fell to the Mongols. The destruction of Aleppo caused panic in Muslim Syria. Damascus capitulated after the arrival of the Mongol army, but was not sacked like other captured Muslim cities. The Mongols proceeded by conquering Samaria, killing most of the Ayyubid garrison in Nablus, and then advanced south, as far as Gaza, unhindered. An-Nasir Yusuf was soon captured by the Mongols and used to persuade the garrison at Ajlun to capitulate.;

On 3 September 1260, the Egypt-based Mamluk army led by Qutuz and Baibars challenged Mongol authority and decisively defeated their forces in the Battle of Ain Jalut, outside of Zir'in in the Jezreel Valley. Five days later, the Mamluks took Damascus and within a month, most of Syria was in Bahri Mamluk hands. Meanwhile, an-Nasir Yusuf was killed in captivity.

Despite their relatively short tenure, the Ayyubid dynasty had a transformative effect on the region, particularly Egypt. Under the Ayyubids, Egypt, which had previously been a formally Shi'a caliphate, became the dominant Sunni political and military force, and the economic and cultural centre of the region, a status that it would retain until it was conquered by the Ottomans in 1517. Throughout the sultanate, Ayyubid rule ushered in an era of economic prosperity, and the facilities and patronage provided by the Ayyubids led to a resurgence in intellectual activity in the Islamic world. This period was also marked by an Ayyubid process of vigorously strengthening Sunni Muslim dominance in the region by constructing numerous madrasas (Islamic schools of law) in their major cities. Even after being toppled by the Mamluk Sultanate, the sultanate built by Saladin and the Ayyubids would continue in Egypt, the Levant and the Hijaz for another 267 years.