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The siege of Zeira in 349 came at the start of Philip II of Macedon's
campaign against Olynthus and Chalcidice, and saw him capture and destroy the
city. Early in his reign Philip had formed an alliance with the Chalcidic
League, and in 356 had even captured the city of Potidaea and handed it over to
the League. Over the next few years his relationship with the league slowly
worsened. Olynthus began to make overtures towards Athens, although didn't form
an alliance, as that would have breached the terms of the alliance with Philip.
In 351, on his way back from the siege of Heraeum, Philip marched through
League territory, in an attempt to intimidate Olynthus. This effort failed, and
may even have encouraged Olynthus to give refuge to Philip's half brothers
Arrhidaeus and Menelaus.
War between Philip and the League began in 347. He crossed the border, and
attacked the fortress of Zereia or Zeira. This place is otherwise unknown and
it probably didn't delay Philip for long. The fortress was besieged and
destroyed. In the aftermath of this success other nearby towns surrendered to
Philip in order to avoid sharing the same fate. It is possible that Zereia was
in Pallene, as this area was raided by the second Athenian expedition sent to
help Olynthus. Philip was probably planning to attack Olynthus itself in the
same year, but he was distracted by trouble in Thessaly. He had previously
expelled the Tyrants of Pherae, but one of them, Peitholaus, appears to have
regained control of the city. This forced Philip to leave Chalcidice to
campaign in Thessaly, where he quickly expelled Peitholaus once again. This was
only a temporary reprieve for Olynthus, although it did make Philip's task
harder. By the time he returned to besiege Olynthus in 348 the Athenians were
ready to send help, but even their three expeditions were unable to save the
city.
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