Stabilization of resistance (1209–1216) When their armistice expired in 1209, Henry returned to fighting against Theodore Laskaris. As part of the struggle, the Latin Empire concluded a secret alliance with Sultan Kaykhusraw. The establishment of a Byzantine center of power in Nicaea had intensified the long-running
Byzantine–Seljuk conflict, with the Empire of Nicaea having become a new major obstacle for westward Seljuk expansion. Michael of Epirus paid the Latin regime a ransom for his cousin, Alexios III, and sent the former emperor to Kaykhusraw. Kaykhusraw could use Alexios to disguise his plans for conquest under a veneer of legitimacy, demanding that Laskaris abdicate in favor of the "more legitimate" emperor. Michael took part in the scheme only to diminish Laskaris's position in favor of his own, not to demonstrate loyalty to the Latins. In 1210, Michael invaded the Kingdom of Thessalonica and captured Thessaly. For this he was excommunicated by Pope Innocent III, ending Epirus's nominal adherence to Catholicism. To protect himself, Michael accepted Venetian suzerainty, though most of Venice's forces were busy capturing Crete from the Genoese. Henry defeated Michael in Thessaly and he was made a Latin vassal again. To rival the Latin–Seljuk alliance, Laskaris allied with Boril in Bulgaria, though Henry defeated a Bulgarian force attacking the Kingdom of Thessalonica. Laskaris had to postpone his plans of a naval attack on Constantinople to counteract the threat posed by Kaykhusraw. With a force of two thousand soldiers, out of which 800 were Latin mercenaries, Laskaris was victorious against Rum in the
Battle of Antioch on the Meander in late spring 1211. Kaykhusraw was killed in battle and Alexios III was captured and then forced to live out his life in a monastery. Peace was forged between Nicaea and Rum, now ruled by Kaykhusraw's son
Kaykaus I. The victory was followed by defeat against the Latins as Henry defeated Laskaris in the
Battle of the Rhyndacus on 15 October 1211. The Latins could occupy the northwestern corner of Anatolia, though both empires were exhausted on manpower. In either 1212 of 1214, the Latin Empire and Nicaea signed the
Treaty of Nymphaeum, in which the Latins were allowed to retain northwestern Anatolia as far as Adramyttium in the south, the rest being left to Nicaea. The Nicene–Bulgarian alliance came to an end in 1213, when a papal legate managed to forge an alliance between Boril and Henry, who conducted an unsuccessful joint campaign against
Stefan Nemanjić of
Serbia. at
Sinope While the Latins were focused on the Nicenes, Michael of Epirus again expanded his influence. He once more conquered western Thessaly from the Kingdom of Thessalonica and renounced Venetian suzerainty, capturing both Dyrrachium and
Corfu from the Venetians in 1213–1214. The Epirote state began to set itself up as an independent Byzantine realm, becoming a center of Byzantine cultural and political tradition similar to Nicaea. In addition to his successful military efforts, Michael became known for his cruelty against the Latins, reportedly executing Latin priests and crucifying a Latin general and his companions. The third Byzantine pretender, Alexios of Trebizond, meanwhile suffered severe setbacks. After recovering from his defeat by the Latins, Laskaris attacked David Komnenos, who was unable to oppose him without Latin support. Laskaris capturing Heraclea Pontica,
Amastris, and all of David's other territories, forcing David to flee to
Sinope. Sultan Kaykaus took advantage of the situation,
capturing Sinope and killing David. When Alexios of Trebizond arrived to retake the city, he was also defeated and captured. In order to secure his freedom, Alexios had to formally surrender Sinope to Kaykaus and agree to become the sultan's vassal. The fall of Sinope diminished Alexios's status as well as the influence of the Empire of Trebizond, which ceased to be a major contender in the Byzantine world. Around the beginning of 1215, Michael of Epirus was assassinated. He was succeeded in Epirus by his half-brother,
Theodore Komnenos Doukas, who after 1204 had spent many years in the Empire of Nicaea and had only returned to Epirus at Michael's request. Theodore taxed his subjects harshly to finance ambitious and successful military campaigns. His first victory came against Boril and Epirus seized
Ohrid and much of the
Vardar valley from the Bulgarians. Henry resolved to stop the growing Epirote threat and marched against Theodore but died at Thessalonica in the spring of 1216.
Rise of Epirus (1216–1225) The Latin barons of Constantinople elected
Peter of Courtenay, husband of Henry's sister
Yolanda, as Henry's successor. In France at the time, Peter traveled to
Rome and was crowned emperor of Constantinople by
Pope Honorius III. The new emperor gathered an army and landed near Dyrrachium in 1217, sending his wife to Constantinople while preparing to wage war on the Epirotes. Peter was almost immediately ambushed and defeated in the Albanian mountain passes by Theodore Komnenos Doukas. Since he is never heard from again, Peter was probably killed. In his place, Yolanda became ruling empress in Constantinople. The Latin Empire was in a precarious position. In 1218, Boril of Bulgaria was overthrown by
Ivan Asen II, removing Yolanda's only remaining ally in her immediate surroundings. Peace was maintained with the Empire of Nicaea through the 1219 marriage of Theodore Laskaris to
Maria of Courtenay, niece of emperors Baldwin and Henry. Upon Yolanda's death in 1219, the throne was inherited by her young son
Robert of Courtenay, who did not arrive in the city until 1221. Theodore Laskaris died late in the autumn of 1221 and was succeeded as emperor at Nicaea by his son-in-law,
John Doukas Vatatzes. John's accession was disputed by Laskaris's brothers,
Alexios and
Isaac, and he transferred his seat of power south to
Nymphaion, further away from the Latin border. In early 1222, Alexios of Trebizond died, the last of the original successors. Alexios was succeeded by his son-in-law,
Andronikos Gidos, who continued to rule Trebizond as an isolated Seljuk vassal. In the west, Theodore of Epirus steadily expanded his realm, focusing his efforts on the Kingdom of Thessalonica. The death of Boniface, weakened Latin leadership, and return of many Latin knights to Western Europe had effectively paralyzed the kingdom. By the early 1220s, Theodore had conquered virtually the entire state, save for Thessalonica itself, which constantly called for aid from Constantinople. In 1223/1224, Emperor Robert divided his forces, sending troops both to relieve Thessalonica and to attack John Doukas Vatatzes of Nicaea. Vatatzes defeated the forces sent against him at the
Battle of Poimanenon, a victory which allowed him to push the Latins out of most of Anatolia. Both of his rebel brothers-in-law Alexios and Isaac, who had sided with the Latin army, were captured and blinded. Once the Latin army in the west heard of Vatatzes's victory they abandoned a siege of Epirote-held
Serres. Without hope for military aid, the Latins of Thessalonica surrendered their city to Theodore Komnenos Doukas near the end of 1224, bringing an end to the Kingdom of Thessalonica, the most important Latin vassal state. Despite its effects abroad, Vatatzes's victories were not enough to ensure his position domestically. Already in 1225 the emperor had to root out a conspiracy against him, organized by his cousins
Andronikos and
Isaac Nestongos. , and later the
Empire of Thessalonica, 1205–1230|upright=1.2 With the capture of Thessalonica, Theodore Komnenos Doukas now held the Byzantine Empire's second most important city and governed a realm that included Epirus, Thessaly, and much of
Macedonia, somewhat larger than the Empire of Nicaea. Theodore refused to recognize the religious authority of the patriarch at Nicaea, as well as the imperial titles of John Doukas Vatatzes or Andronikos Gidos. Supported by the Epirote clergy, Theodore reestablished the former Byzantine ecclesiastical administrations in the reconquered territories, though prelates were appointed by provincial synods rather than the permanent synod under the patriarch. At some point in 1225–1227, Theodore assumed the imperial title and was crowned by
Demetrios Chomatenos,
Archbishop of Ohrid, establishing what historians refer to as the '
Empire of Thessalonica'. Theodore was deemed a usurper by both John Doukas Vatatzes and his patriarch,
Germanus II Nauplius. Theodore's supporters could however point to him having been proclaimed emperor through traditional means, and argued that he deserved to be emperor for his virtues and military successes, and through his descent from former emperors. His coronation in opposition to Nicaea was further justified as legitimate since both empires were provisional states created out of "odd circumstances" and the "confusion of the times". The Epirotes argued that the legitimate and real empire would only be reinstated once the Latins were driven from Constantinople and a Byzantine emperor and their patriarch once more held Constantinople.
First attempts on Constantinople (1225–1236) In 1225, the Byzantine people of Adrianople invited John Doukas Vatatzes to liberate their city. A Nicene force successfully captured the city and seized the land between it and the sea. A few months later, Theodore of Thessalonica arrived with a much larger force and the Nicene garrison surrendered Adrianople without fighting. Theodore concluded an alliance with Ivan Asen of Bulgaria through a dynastic marriage and then captured most of the rest of Thrace, reaching the walls of Constantinople. At the height of his power, Theodore aspired not only to take the city, but to restore the entire old empire. His rapid rise caused his rivals to unite against him. Vatatzes began to support the Latin emperor Robert, and Asen also began to open negotiations with the Latins. Threatened with the prospect of a coalition against him, Theodore hesitated to march on Constantinople. In 1228, Robert died and the Latin throne was inherited by his underage brother
Baldwin II. Asen warned Theodore to not seize the opportunity to attack Constantinople, since the Bulgarian ruler wished to marry his daughter to the new emperor. In September 1228, Theodore thus concluded a truce with the Latins, establishing commercial relations and a right of return for refugees. The Bulgarian opposition to an attack on Constantinople ended when the Latin barons of the city shut down the idea of a Bulgarian marriage, fearing that Asen would take control of the empire as Baldwin's father-in-law. Instead,
John of Brienne, the aged former
king of Jerusalem, was invited to become senior co-emperor. In the spring of 1230, Theodore broke his alliance with Asen and marched up the
Maritsa river into Bulgaria, with an army of Byzantines and Latin mercenaries. Theodore likely sought to check Bulgarian power and avoid the threat of a Bulgarian attack in his rear if he were to move on Constantinople. Asen was caught by surprise and hung the text of his broken treaty with Theodore from his standards. On 9 March 1230, the Bulgarians inflicted a crushing defeat on Theodore at the
Battle of Klokotnitsa. Theodore himself was taken captive, alongside many of his generals. At some point during his captivity, Theodore was blinded by Asen after being accused of being part of a conspiracy. under
Ivan Asen II, after 1230|upright=1.2 The defeat at Klokotnitsa shattered the Empire of Thessalonica. In its place, Bulgaria emerged as the strongest power in the Balkans, taking control over much of Thrace, Macedonia, and Albania. Unlike Kaloyan, Ivan Asen was a milder imperial overlord. Epirus became practically independent under
Michael II Komnenos Doukas, illegitimate son of the first Michael of Epirus. Theodore's brother
Manuel Doukas escaped Klokotnitsa unharmed and seized power in Thessalonica. Manuel controlled a much reduced domain, effectively being a Bulgarian client ruler, and quickly recognized the imperial authority of Vatatzes and the religious authority of his patriarch in order to "heal the dissension among us Romans". Manuel officially ruled as
despot (not emperor) but continued to use 'emperor' in certain documents and to sign his decrees with red ink, an imperial prerogative. In 1231, Ivan Asen challenged the authority of the Byzantine pretenders by taking the title 'Emperor and Autocrat of the Bulgarians and Romans', beginning to aspire to conquer Constantinople and revive the Byzantine Empire under himself. In 1231, John of Brienne arrived to lead the failing Latin Empire. Vatatzes avoided conflict with Asen and instead focused on expanding his power in other ways. A Seljuk invasion of the Meander valley was defeated,
Lesbos,
Chios, and
Samos were reconquered from the Latins, and Vatatzes aided a revolt by the natives of Crete against the Venetians. Vatatzes also tried to negotiate with
Pope Gregory IX, offering to work on reuniting the Catholic and Orthodox churches in return for the surrender of the Latin Empire. Meanwhile, Asen worked on increasing the power and autonomy of the
Bulgarian church. Byzantine bishops were replaced with Bulgarians in several cities and attempts were made to integrate Thessalonica and
Mount Athos under the Bulgarian church. While Vatatzes fought against Leo Gabalas of Rhodes in 1234, John of Brienne invaded Anatolia. The attack made Vatatzes abandon his negotiations with the papacy and conclude an anti-Latin alliance with Asen in 1235. The alliance was sealed through the marriage of Vatatzes's son,
Theodore II Laskaris, and Asen's daughter
Elena Asanina. In conjunction with the alliance, Nicene authorities recognized the Bulgarian church leader
Joachim I as a patriarch and the Bulgarian church as
autocephalous, affirmed by
Germanus II of Constantinople (Nicaea),
Dorotheus of Antioch, and
Nicholas I of Alexandria. Any ties of the Bulgarian church to the papacy were severed and it was firmly placed back in the Orthodox orbit. In return, Asen accepted Germanus II's religious jurisdiction over Thessalonica and Mount Athos. Asen and Vatatzes agreed to partition Thrace, with Bulgaria to gain the north and Nicaea to gain the south (including Constantinople). In light of the alliance, Patriarch Germanus II preached total war on "the western people" to "send them packing, back to their own countries". Germanus referred to the Byzantines of his time as the "humiliated generation" and publicly encouraged Vatatzes to "rebaptize the Latins in their own blood". In 1235, Bulgaria and Nicaea launched a
joint attack on Constantinople. As per their agreement, Nicaea took most of southern Thrace and Bulgaria took the north. Vatatzes and Asen besieged Constantinople together, with Leo Gabalas joining them and commanding a Byzantine fleet. The two were forced to lift the siege due to the arrival of John of Brienne,
Geoffrey II of Villehardouin, and a Venetian fleet. In early 1236, another joint siege was attempted, though it too ended in failure.
Rise of Nicaea (1236–1248) John of Brienne died of old age in 1237, at a time when the young Baldwin II was away from Constantinople, traveling through Italy asking for aid. Though another joint attack on Constantinople may have been fruitful, Asen realized that Vatatzes was the chief beneficiary of the Latin Empire's downfall. Perhaps motivated by his own desire to take Constantinople, Asen broke his marriage agreement with Vatatzes, recalling his daughter to Bulgaria. He also made a treaty with the Latins and joined a Latin siege of the Nicene-held Tzurulum. Asen furthermore released the blinded Theodore Komnenos Doukas from captivity and married Theodore's daughter,
Irene. Theodore made his way to Thessalonica and organized an uprising against Manuel, who fled to Turkish territory. Since Theodore could no longer officially rule himself, he had his younger son
John Komnenos Doukas crowned as emperor in Thessalonica while he himself held the real power form the nearby town of
Vodena. An outbreak of the
plague in Bulgaria, which killed both high church officials and several of Asen's immediate family members was interpreted by the Bulgarian emperor as divine wrath for his treachery against the Nicenes. Asen ended his participation in the siege of Tzurulum, returned his daughter to Nicaea, and renewed his alliance. At the same time, Manuel Doukas resurfaced at Nicaea and Vatatzes agreed to help him retake Thessalonica. In early 1239, Manuel and a Nicene force landed in Thessaly, though Theodore stopped the invasion diplomatically by allowing Manuel to govern Thessaly under Thessalonian suzerainty. Later in the same year, Baldwin II returned to Constantinople, backed by an army of French soldiers he had raised through selling a Byzantine relic purported to be the
crown of thorns to
Louis IX of France. The Latin army, also joined by a force of
Cumans fleeing the
Mongols, captured Tzurulum from Nicaea in 1240. In retaliation, Vatatzes managed to capture Nicomedia from the Latins in a naval campaign. (1243) from
Hayton of Corycus's ''Fleur des histoires d'orient''.|upright=1.2 Ivan Asen died in 1241 and was succeeded by his young son
Kaliman Asen I and a group of regents. The death of its strong leader weakened the Bulgarian Empire, which was already suffering from internal quarrels and external pressure from the Mongols to its north. Ivan Asen's successors ceased to claim to be Byzantine emperors, returning to styling themselves as 'Emperor and Autocrat of the Bulgarians'. The weakening of Bulgaria again strengthened the Komnenoi Doukai in the west. Vatatzes invited Theodore to Nicaea, ostensibly to discuss an anti-Latin alliance, and then imprisoned him. Vatatzes went on to conclude a two-year truce with the Latin Empire and managed to win over its Cuman allies through granting them lands along the Anatolian border. In the spring of 1242, Vatatzes and the Cumans launched an attack on John of Thessalonica and Michael II of Epirus (who now also ruled Thessaly following Manuel's death). Thessalonica was placed under siege, though the siege was interrupted once Vatatzes heard that the Mongols had invaded the Sultanate of Rum. Worried about the prospect of the Mongols reaching his own lands, Vatatzes cut the campaign short. Thessalonica and Epirus were allowed to remain independent, though Vatatzes annexed some Thracian territory and made John give up the title of emperor in favor of
despot, nominally under Nicene suzerainty. Wishing to stop the Mongols from penetrating into Anatolia, Vatatzes concluded an alliance with Sultan
Kaykhusraw II of Rum in 1243, promising to send him a detachment of 400 soldiers. In total, Kaykhusraw was joined by 3,000 Christian soldiers, also including forces sent by the Latin Empire and by
Manuel Komnenos, the emperor of Trebizond. On 26 June 1243, the Mongols decisively defeated the assembled army at the
Battle of Köse Dağ. Both the Sultanate of Rum and the Empire of Trebizond were forced to become tributary vassals to the Mongols. The Empire of Nicaea emerged from the battle unharmed, however, and even benefitted from the weakening of its neighbors after the Mongols were diverted from Anatolia by pressing matters elsewhere. In the summer of 1246, Kaliman Asen died and was succeeded in Bulgaria by his brother
Michael Asen, only a child. Vatatzes broke his treaty with the Bulgarians and captured Serres, whereafter he was able to capture large swaths of territory from the Bulgarians almost unopposed, including cities such as Adrianople and lands all the way to the foothills of the
Balkan Mountains. Michael II of Epirus took the chance to capture Ohrid from the Bulgarians. In reaction to Vatatzes's success, the populace of Thessalonica organized a conspiracy in his favor. Vatatzes was able to capture the city without resistance, with the
despot Demetrios Angelos Doukas (having succeeded John in 1244) being deposed and exiled to Anatolia. In the spring of 1247, Vatatzes attacked the Latins, their truce having expired, and recaptured Tzurulum. The Nicene emperor now surrounded the capital. In 1248, Michael of Epirus recognized Vatatzes as emperor and was in return formally bestowed with the title of
despot. As the Latin Empire was bankrupt and doomed,
Pope Innocent IV began to seriously consider Vatatzes's former offer of surrendering the Latin Empire in return for reuniting the churches. == Fall of the Latin Empire (1248–1261) ==