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Manuel II Palaiologos
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===Siege of Constantinople and letters to European courts=== Having heard of his father's death in February 1391, Manuel II Palaiologos fled the Ottoman court and secured the capital against any potential claim by his nephew John VII.{{sfn|Barker|1969|p=xxiv}} Following Manuel's joint marriage-coronation in 1392 with [[Helena Dragaš]], the daughter of fellow Ottoman vassal [[Helena Dragaš|Constantine]] [[Konstantin Dejanović|Dragaš]], the Sultan was initially content to leave New Rome in comparative peace.<ref>Çelik 2021, pp. 157-160</ref> However, in 1393 a large insurrection erupted in Bulgaria which, although successfully put down by the Ottomans, caused Bayezid to lapse into an episode of paranoia in which he believed his various Christian vassals were plotting against him. Bayezid called all his Christian vassals to a meeting at [[Serres]], with the intention of massacring them, a decision he relented on only at the last moment. The episode is said to have left all of the Christian vassal rulers shaken and convinced Manuel that continued appeasement towards the Ottomans was not a guarantee of his own personal safety or the continued survival of the empire and that efforts must be made to obtain Western aid.{{sfn|Norwich|1995|pp=351–354}} Sultan Bayezid I [[Siege of Constantinople (1394–1402)|blockaded]] [[Constantinople]] from 1394 to 1402. In the meantime, an anti-Ottoman crusade led by the [[Kingdom of Hungary|Hungarian]] King [[Sigismund, Holy Roman Emperor|Sigismund of Luxemburg]] failed at the [[Battle of Nicopolis]] on 25 September 1396. Manuel II had sent 10 ships to help in that Crusade. In October 1397, [[Theodore Kantakouzenos]], Manuel's uncle, alongside John of Natala arrived at the court of [[Charles VI of France]], bearing the Emperor's letters (dated 1 July 1397) requesting the French king's military aid. In addition, Charles also provided funds for the two nobles to treat with King [[Richard II of England]] in April 1398, with the aim of soliciting further aid.{{sfn|Hinterberger|Schabel|2011|p=397}} However, the latter was too preoccupied by domestic troubles at this point to provide any support.{{efn|In addition, Ilario Doria, Manuel's son-in-law, was also sent with a delegation to Italy, England, and probably France, early in 1399.{{sfn|Hinterberger|Schabel|2011|p=397}}}} However, the two nobles returned home with the [[Marshal of France]] [[Jean II Le Maingre]] who was sent from [[Aigues-Mortes]] with six ships carrying 1,200 men to assist Manuel II. The Marshal encouraged the latter to go personally to seek assistance against the [[Ottoman Empire]] from the courts of western Europe. After some five years of siege, Manuel II entrusted the city to his nephew, aided by a French garrison of 300 men led by Seigneur [[:fr:Jean de Châteaumorand|Jean de Châteaumorand]] and embarked (along with a suite of 40 people) on a long trip abroad along with the Marshal.{{sfn|Hinterberger|Schabel|2011|p=398}}
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