Saladin in the context of "Citadel of Cairo"

Richard I (8 September 1157 – 6 April 1199), known as Richard the Lionheart or Richard Cœur de Lion (Old Norman French: Quor de Lion) because of his reputation as a great military leader and warrior, was King of England from 1189 until his death in 1199. He also ruled as Duke of Normandy, Aquitaine, and Gascony; Lord of Cyprus; Count of Poitiers, Anjou, Maine, and Nantes; and was overlord of Brittany at various times during the same period. He was the third of five sons of Henry II of England and Eleanor of Aquitaine and was therefore not expected to become king, but his two elder brothers predeceased their father.

By the age of 16, Richard had taken command of his own army, putting down rebellions in Poitou against his father. Richard was an important Christian commander during the Third Crusade, leading the campaign after the departure of Philip II of France. Despite achieving several victories against his Muslim counterpart, Saladin, he was ultimately forced to end his campaign without retaking Jerusalem.

The Crusades were a series of military campaigns launched by the papacy between 1095 and 1291 against Muslim rulers for the recovery and defence of the Holy Land (Palestine), encouraged by promises of spiritual reward. The First Crusade was proclaimed by Pope Urban II at the Council of Clermont on 27 November 1095 in response to a Byzantine appeal for aid against the advancing Seljuk Turks. By this time, the papacy's position as head of the Catholic Church had strengthened, and earlier conflicts with secular rulers and wars on Western Christendom's frontiers had prepared it for the direction of armed force in religious causes. The First Crusade led to the creation of four Crusader states in the Middle East, whose defence required further expeditions from Catholic Europe. The organisation of such large-scale campaigns demanded complex religious, social, and economic institutions, including crusade indulgences, military orders, and the taxation of clerical income. Over time, the crusading movement expanded to include campaigns against pagans, Christian dissidents, and other enemies of the papacy, promoted with similar spiritual rewards and continuing into the 18th century.

The Crusade of 1101, the earliest papally sanctioned expedition inspired by the First Crusade, ended in disastrous defeats. For several decades thereafter, only smaller expeditions reached the Holy Land, yet their role in consolidating and expanding the Crusader states was pivotal. The fall of Edessa, the capital of the first Crusader state, prompted the Second Crusade, which failed in 1148. Its failure reduced support for crusading across Latin Christendom, leaving the Crusader states unable to resist Saladin's expansion. Having united Egypt and Muslim Syria under his rule, Saladin destroyed their combined armies at the Battle of Hattin in 1187. The Crusader states survived largely owing to the Third Crusade, a major campaign against Saladin, though Jerusalem remained under Muslim control. Initially directed against Egypt, the Fourth Crusade was diverted to the Byzantine Empire, culminating in the Sack of Constantinople and the establishment of the Latin Empire in 1204. The Fifth Crusade again targeted Egypt but failed to conquer it in 1219–21. By this period, crusade indulgences could also be obtained through other campaigns—such as the Iberian, Albigensian, and Northern Crusades—thereby diminishing enthusiasm for expeditions in the eastern Mediterranean.

The Ayyubid dynasty (Arabic: الأيوبيون, romanized: al-Ayyūbīyūn), also known as the Ayyubid Sultanate, was the founding dynasty of the medieval Sultanate of Egypt established by Saladin in 1171, following his abolition of the Fatimid Caliphate of Egypt. A Sunni Muslim of Kurdish origin, Saladin had originally served the Zengid ruler Nur al-Din, leading the latter's army against the Crusaders in Fatimid Egypt, where he was made vizier. Following the death of his Zengid suzerain Nur al-Din in 1174, Saladin was proclaimed as the first Sultan of Egypt by the Abbasid Caliphate, and rapidly expanded the new sultanate beyond Egypt to encompass most of Syria, in addition to Hijaz, Yemen, northern Nubia, Tripolitania and Upper Mesopotamia. Saladin's military campaigns set the general borders and sphere of influence of the sultanate of Egypt for the almost 350 years of its existence. Most of the Crusader states fell to Saladin after his victory at the Battle of Hattin in 1187, but the Crusaders reconquered the Syrian coastlands in the 1190s.

After Saladin's death in 1193, his sons contested control of the sultanate, but Saladin's brother al-Adil ultimately became sultan in 1200. All of the later Ayyubid sultans of Egypt were his descendants. In the 1230s, the emirs of Syria attempted to assert their independence from Egypt and the Ayyubid realm remained divided until Sultan as-Salih Ayyub restored its unity by subduing most of Syria, except Aleppo, by 1247. By then, local Muslim dynasties had driven out the Ayyubids from Yemen, the Hejaz, and parts of Mesopotamia. After his death in 1249, as-Salih Ayyub was succeeded in Egypt by his son al-Mu'azzam Turanshah. However, the latter was soon overthrown by his Mamluk generals who had repelled a Crusader invasion of the Nile Delta. This effectively ended Ayyubid power in Egypt. Attempts by the emirs of Syria, led by an-Nasir Yusuf of Aleppo, to wrest back Egypt failed. In 1260, the Mongols sacked Aleppo and conquered the Ayyubids' remaining territories soon after. The Mamluks, who expelled the Mongols, maintained the Ayyubid principality of Hama until deposing its last ruler in 1341.

The Third Crusade (1189–1192) was an attempt led by King Philip II of France, King Richard I of England and Emperor Frederick Barbarossa to reconquer the Holy Land following the capture of Jerusalem by the Ayyubid sultan Saladin in 1187. For this reason, the Third Crusade is also known as the Kings' Crusade.

It was partially successful, recapturing the important cities of Acre and Jaffa, and reversing most of Saladin's conquests, but it failed to recapture Jerusalem, which was the major aim of the Crusade and its religious focus.

The Battle of Hattin took place on 4 July 1187, between the Crusader states of the Levant and the forces of the Ayyubid sultan Saladin. It is also known as the Battle of the Horns of Hattin, due to the shape of the nearby extinct volcano of that name.

The Muslim armies under Saladin captured or killed the vast majority of the Crusader forces, removing their capability to wage war. As a direct result of the battle, Muslims once again became the eminent military power in the Holy Land, re-capturing Jerusalem and most of the other Crusader-held cities and castles. These Christian defeats prompted the Third Crusade, which began two years after the Battle of Hattin.

The Fifth Crusade (September 1217 – August 29, 1221) was a campaign in a series of Crusades by Western Europeans to reacquire Jerusalem and the rest of the Holy Land by first conquering Egypt, ruled by the powerful Ayyubid sultanate, led by al-Adil, brother of Saladin.

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, titular King of Jerusalem. 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. There, cardinal Pelagius Galvani arrived as papal legate and de facto leader of the Crusade, supported by John of Brienne and the masters of the Templars, Hospitallers and Teutonic Knights. Holy Roman Emperor Frederick II, who had taken the cross in 1215, did not participate as promised.

The Kingdom of Jerusalem, also known as the Crusader Kingdom, was one of the Crusader states established in the Levant immediately after the First Crusade. It lasted for almost 200 years, from the accession of Godfrey of Bouillon in 1099 until the fall of Acre in 1291. Its history is divided into two periods with a brief interruption in its existence, beginning with its collapse after the siege of Jerusalem in 1187 and its restoration after the Third Crusade in 1192.

The original kingdom lasted from 1099 to 1187 before being almost entirely overrun by the Ayyubid Sultanate under Saladin. Following the Third Crusade, it was re-established in Acre in 1192. The re-established state is commonly known as the "Second Kingdom of Jerusalem" or alternatively as the "Kingdom of Acre" after its new capital city. Acre remained the capital for the rest of its existence, even during the two decades that followed the Crusaders' establishment of partial control over Jerusalem during the Sixth Crusade, through the diplomacy of Emperor Frederick II.