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Kalapothakis was born in 1865 in Areopoli. He abandoned his studies in the University of Athens, when Thessaly was annexed to Greece in 1881 he went to Volos where he started publishing his newspaper Simaia ("Flag"). For many years, Kalapothakis was a political columnist who openly supported Charilaos Trikoupis. After the latter's death he started publishing the Embros ("Forward") newspaper. Kalapothakis was one of the most important personalities of the Greek press as a reporter and also one of the many organisers of the Hellenic Macedonian Committee in 1904. He joined for the purpose of stopping Bulgarian domination in Macedonia and he provided guns, money and equipment to the Macedonian fighters (Makedonomachoi). He was the leader of the committee until its final dissolution in 1908. During the National Schism he sided with the King.
During his life he also wrote many theatric plays. Kalapothakis died in Germany in May 1921 during a surgery operation.
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