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1264 Battle of Makryplagi ★ ★ ★ ★ ★
Outcome: A defeat of the Byzantines by the Latins of the Principality of Achaea 1264 or 1265
War  &  Enemy: Enemy:
Franks
War:
Byzantine-Latin Wars
Battle Type:
Pitched Battle
The Battlefield Makryplagi Location:
In the mountain passage between Arcadia and north Messenia in Peloponnese, between modern villages Tourkolias and Kalyvia.
Modern Country:
Greece
  The Byzantines(emperor:  Michael VIII Palaiologos) The Enemies
Commander: Generals Alexios Philes & John Makrenos Prince William II of Villehardouin
Forces: Unknown Unknown
Losses:
Background story: After the Battle of Pelagonia (1259), the Byzantine emperor Michael VIII Palaiologos acquired a number of fortresses in the southeastern Peloponnese (Moreas) like Mystras and Monemvasia, ceded by the captured Prince of Achaea William II of Villehardouin in exchange for his freedom. William also pledged to become Michael's vassal, but as soon as he returned to the Moreas he renounced this oath, and began negotiating with the Pope and other Latin powers for a joint effort against the Byzantines.
War broke out in late 1262, when Michael VIII dispatched an expedition to the Moreas. This army was composed chiefly of Turkish mercenaries and Greek troops from Asia Minor and headed by his half-brother, the sebastokrator Constantine Palaiologos. Constantine enjoyed initial success, capturing much of Laconia and advancing north, aiming to take the Achaean capital, Andravida. He was defeated,, however by a far smaller Latin force at the Battle of Prinitza, and his army scattered,
In early 1263 or 1264, Constantine Palaiologos resumed operations against the Principality of Achaea for good. He advanced up to Sergiana in northern Elis, and set up his camp at a location called St. Nicholas of Mesiskli. William with his own troops marched to meet him, and arrayed his men ready for battle. According to the Chronicle of the Moreas, the head of the Byzantine vanguard, the megas Kontostavlos Michael Kantakouzenos, rode forth from the Byzantine lines, but his horse stumbled and he was killed by the Achaeans. Dismayed by the death of his bravest lieutenant, the sebastocrator Constantine retreated and went on to lay siege to the fortress of Nikli.
There, however, the Turkish mercenaries, over 1,000 horsemen under their leaders Melik and Shalik, confronted him and demanded that he pay them their arrears of six months. Irritated by this demand, and worried by his lack of success thus far, the sebastocrator angrily refused, whereupon the two chieftains deserted to William with the bulk of their men. This defection caused Byzantine morale to plummet. Constantine, feigning illness, decided to raise the siege, and departed the Moreas for Constantinople, leaving the megas domestikos Alexios Philes and the parakoimomenos John Makrenos in command.
The Battle:
Makryplagi
Alexios Philes took The Byzantine army and marched towards Messenia, where he occupied the pass of Makryplagi, situated near Gardiki castle at the borders of Messenia with the central Peloponnese. William, reinforced by the experienced Turkish contingent and now possessing a superior army, had marched to Messenia to defend the fertile province. The Achaean army now attacked the Byzantines, despite the fact that they held strong positions on the high ground. The first two attacks were beaten off, but the third attack, led by William's commander Ancelin de Toucy, broke the Byzantines, who fled in panic.Ancelin de Toucy The Byzantine rout was complete. The generals Philes, Makrenos, and Alexios Kaballarios, along with many Greek nobles, were captured.
Noteworthy:
Aftermath: William tried to capture Mystras and failed. After the two major defeats of the expedition force, the Byzantines abandoned their plans to take Moreas. William prevailed but he had exhausted the resources of his principality.