In mid-342 BC Philip decided it was time to subdue eastern Thrace. If he succeeded then Athenian influence in the northern Aegean would be eliminated and Athens’ vital grain route to the Black Sea would be compromised. However, Philip’s campaign was not aimed solely at the Athenians. Artaxerxes had regained Cyprus (344 BC), Phoenicia and Egypt (343 BC), and sent Mentor of Rhodes (c.385-340 BC) to restore order in Asia Minor (342 BC). A resurgent Persian Empire might change the balance of power in the Aegean. Philip thought he could prevent this by extending his authority up to the straits.
An attack by the Odrysians under Cersobleptes and Teres II (r.351-341 BC) on neighbouring Greeks gave Philip his excuse to take action. All that is known about this is that it peaked in 341 BC with the defeat of Cersobleptes and Teres in separate engagements, leaving Philip clear to reduce the few remaining hilltop fortifications and claim the Odrysian realm.
In 343/2 BC the Athenians had sent additional cleruchs to the Chersonese led by Diopeithes. There he acted aggressively to strengthen Athenian control of the peninsula. In particular, when the Cardians refused to accept the cleruchs, he attacked their territory. In 342/1 BC the Cardians in turn appealed to their ally Philip, who wrote to Athens demanding that Diopeithes ceased his activities and then sent a force of mercenaries to support Cardia.
It was in response to Philip’s letter that Demosthenes delivered his speech On the Chersonese in which he insists that Philip had already broken the peace and was already in a state of (undeclared) war with Athens. He argued that Philip’s campaign in eastern Thrace put both the Chersonese and Byzantium under threat, and that Diopeithes should therefore be supported both politically and with further resources.
In summer 340 BC, probably in late July, Philip laid siege to Perinthus in northeastern Thrace. Artaxerxes ordered his satraps on the eastern shore of the Propontis to send mercenaries and supplies to help Perinthus; Byzantium, too, provided men and materials. The Macedonians broke into the town, but were driven out after fierce fighting among the close-packed houses. Philip then divided his army and began an assault simultaneously on Byzantium. Chares, who was already in the vicinity, was sent with his squadron of forty ships to relieve Byzantium, but Chares was distrusted by the Byzantines and he was soon replaced by Phocion. In the autumn Philip captured an Athenian grain convoy of one hundred and eighty ships on the far side of the Bosporus waiting for an escort to take it through the straits.
In 339 BC Philip abandoned his sieges to launch an attack on the Scythian king Ateas (c.90; r.c.400-339 BC), whose kingdom lay north of Odrysia. Ateas not only posed a threat to the recent Odrysian conquests, but had also reneged on sending supplies in support of the Macedonian sieges. Philip summoned his son, the future Alexander III (32; r.336-323 BC), from Macedonia, where he had been acting as regent, to join the expedition and gain experience in war. A battle was fought on the Dobruja Plain to the west of the Black Sea. The Scythians were defeated and Ateas fell during the fight.
Philip gathered his booty and moved westwards along the Danube Valley intending to enter Macedonia from the north by passing through the territory of the Triballi. For a peaceful transit through their land the Triballi demanded a share of Philip’s loot and attacked when he refused. He fought his way through their territory, but he was wounded in the thigh and lost most of the booty.
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