The Trickery of Phillip
Phillip was a commander that left nothing to chance and passed up the opportunity to attack in the spring of 338 BC. This is despite having an army with vast combat experience facing an enemy filled with troops that had never seen the battlefield including Demosthenes. Even so, Phillip used brain over brawn and tricked his enemies with a fake letter to one of his most prominent generals, Antipater. In it, Philip wrote that he was going to rush to Thrace to deal with a revolt there.
He ensured that his courier was captured and the letter seized. The allied commanders of the mercenaries guarding the crucial pass to Amphissa, Chares and Proxenus, believed the contents of the letter and relaxed their guard. When Phillip sent scouts to the pass, he found that it was deserted and burst through. The enemy generals reacted too late and were unable to hold off the enemy. There is some doubt over the veracity of this account because it is the same ruse Philip used during the siege of Byzantium. The odds of an experienced commander like Chares, who was also at Byzantium, falling for the same trick twice are long. Even so, Philip did manage to get through the pass and forced his enemies to retreat to Chaeronea.
The Greek Allied Forces Pay for Their Naivety
Plutarch’s account of the battle suggests that it took place in early August 338 BC as Philip brought 30,000 men to the field. The Greek alliance had a similar number of troops but they had never fought together before. According to Diodorus, Alexander was placed on one wing, possibly the left, with Philip on the right. In contrast to the well-oiled Macedonian machine, the alliance had several commanders including Chares, who was one of the Athenian side’s generals, and Theaganes, who led the Thebans.
Although accounts vary, it is believed that the Athenians occupied the left wing, the Thebans were on the right, and a group of assorted allies was in the middle. This means Alexander faced off against the Thebans while Philip was up against the Athenians. According to Plutarch’s Life of Alexander, the young lion was the first to charge against the Theban Sacred Band, an act of bravery that greatly pleased Philip. The Athenians attacked Philip and were utterly fooled by his decision to order an apparent retreat. In reality, he was luring the enemy into a trap and the inexperienced Athenian army fell for it.
The Athenians marched forward and were joined by their allies in the center. It was a critical blunder because there was now a clear gap between the Athenians & allies, and the Theban army. Alexander, who was given sole command of the cavalry, spotted the gap and immediately charged into it. Alexander’s men attacked the rear and flank of the Thebans who were suddenly in serious danger. The Battle of Chaeronea had raged for several hours but for one side, total defeat was imminent.