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Philip was only a third son and had secured the throne because of his intuitive sense of politics.
His elder brothers, Alexander II and Perdiccas III, had been killed by Illyrians, and he had been originally appointed regent for his infant nephew Amyntas IV, who was Perdiccas’ son, in 359 BC.
Philip nabbed the kingdom for himself that same year, reformed the Macedonian army to rely on a combination of heavy cavalry and phalanxes with ultra-long spears1, and quickly took care of business, defeating barbarian invaders like the Thracians and an Athenian attempt to place a puppet king in Macedonia.
The Macedonian king's idiosyncratic carrot-and-stick approach to all things is evident on his deal with the Illyrians to marry a daughter of their king — right before he went to battle and crushed them. By the time Aristotle arrived in the Macedonian court, a combination of triumphs and diplomatic bullying had turned Philip into the leading warlord of Greece2, and his later campaigns only made this more obvious.
In 338 BC, Philip II marched south with his army and met an alliance of poleis organized by Demosthenes-led Athens and Thebes, who had put their long-standing differences aside to stop the half-barbarian bully.
The Macedonians had perhaps only 30,000 infantry, but a clear advantage through their small but powerful cavalry contingent, 2,000-strong and led by prince Alexander, in overall command of the left wing of the army. In Chaeronea, Boeotia, the southern Greek allies tried to hold a defensive position but were confounded by a series of smart feints ordered by Philip II; and, eventually, what appears to have been an Alexander-driven charge that destroyed the enemy’s left flank.
The Macedonian victory didn’t lead to subjection or occupation. Acting generously, as he usually did in victory, Philip II made peace with his former enemies and ransomed their prisoners, hoping to convince them to join his own grandiose plans to invade the Persian empire that the alarmed Persians had heard of.
As preparations for the campaign continued, Aristotle gave lessons not only to Alexander, but also to two other future kings and generals of Alexander: Ptolemy and Cassander. Surely with Philip's encouragement, Aristotle urged Alexander toward eastern conquest, expressing a hostile attitude towards Persia that, given Hermias' death, is not at all surprising.
In one famous aside, Aristotle counselled Alexander to be "a leader to the Greeks and a despot to the barbarians, to look after the former as after friends and relatives, and to deal with the latter as with beasts or plants.”
Philip was murdered by one of his bodyguards in 336 BC. It's impossible to tell who paid the assassin in this plot, given that the old king had a long string of enemies, from Persians to barbarians to sophisticated southern Greeks.
There have been suggestions that his wife Olympia, probably tired of the hard-drinking, violent despot, had a hand in the deed, perhaps with the acquiescence of young Alexander. In any case, Alexander III rose to the throne and almost immediately went on campaign to re-establish Macedonian control over all of the vassals that had suddenly tried to defect. No longer needed, Aristotle headed back to Athens.
There, Aristotle came across Demosthenes again. Somehow, the lawyer, speech-writer and well-paid tutor of wealthy Athenian kids, a cunning politician of little morals who had opposed Macedonian dominance3, had survived not only the battle of Chaeronea, where he fought as a hoplite, but also the subsequent years of Philip's reign and was agitating against his young son.
Aristotle found that Athens’ democracy remained fickle under Demosthenes as it had been under Pericles, during the lifetime of his master Plato. Sortition and “first come, first serve” arrangements to select magistrates had become common, to avoid elections4 easily swayed by particular oligarchic interests. But silver tongues like Demosthenes still found ways to secure support by spreading half-truths or outright lies5.
FROM THE ARCHIVES:
In 335 BC, as Alexander campaigned against the always battle-happy Thracians and Illyrians, Demosthenes spread one such rumor – delivered by a bloodstained messenger he had arranged for – that Alexander and his expeditionary force had been slaughtered. The Thebans and the Athenians rebelled once again, financed by Persian emperor Darius III with such brazenness that Demosthenes is said to have received about 300 talents (on behalf of Athens) and to have faced accusations of embezzlement because of his inability to share the bribe.
Of course, Alexander hadn't been slaughtered by anyone. He reacted immediately and razed Thebes to the ground. He did not attack Athens, demanding instead the exile of all anti-Macedonian politicians, Demosthenes first of all. According to Plutarch, a special Athenian embassy led by Phocion, an opponent of the anti-Macedonian faction, was able to persuade Alexander to relent and cut a deal: the Athenians would accept his suzerainty, and he would be able to go away to fight the Persians or whatever else caught his fancy.
It's not known whether Aristotle had a hand in any of this, which is not impossible. With Athens pacified without undue bloodshed and destruction and Demosthenes temporarily restrained, Aristotle had the time to establish his own school, the Lyceum, where he conducted courses at the school for the next twelve years. With his students and fellow scholars like the astronomer Callippus, he also set up a working library, the Peripatos, that may have served as inspiration for the future Great Library at Alexandria.
“Sarissa,” very heavy to carry and difficult to operate, but effective to keep enemies at a distance and as anti-missile weapons, a valuable quality particularly in combat against missile-heavy Eastern armies like the Persians’: well-trained phalanxes held their spears at different levels, with some parallel to the ground and others at almost 90 degrees, forming a screen that shielded the phalanx from many projectiles.
Sparta's final moment of classic defiance came during these campaigns. With key Greek city-states in submission, Philip II sent them a message to the effect that, if he were to invade their lands, the Spartans would be sorry. The Spartans' laconic reply was one word: "If". Philip II did invade and devastated much of the Spartan lands but neither he nor his Alexander occupied the city of Sparta, probably out of respect for the Spartans' legendary awesomeness, rather than their less-than-stellar army of the post-Leuctra era.
Demosthenes had conspired for Athenian democracy and against the Macedonians for over a decade by then, the time when he delivered his well-known Philippic speeches, the base for his future fame and still a frequent learned reference for students of rhetoric.
This point is forcefully made in “The Athenian Democracy in the Age of Demosthenes” (1993) by Mogens Herman Hansen. To be eligible to be chosen by lot, citizens self-selected themselves into the available pool, and were then picked through lotteries for a one-year term. A citizen could not hold any particular magistracy more than once in his lifetime, but could hold other magistracies. All non-disenfranchised male citizens over 30 years of age were eligible; although those elected through lot underwent examination called dokimasia in order to avoid incompetent officials, the bar to disqualify a selected citizen was high. Magistrates were later subjected to constant monitoring by the assembly, and those appointed by lot had to render account of their time in office upon their leave, called euthynai. Any citizen could request the suspension of a magistrate with due reason.
In “The Athenian constitution,” written around 350 BC by Aristotle or (more likely) one of his disciples, there's plenty of fascinating detail on how Athens went through various combinations of elections plus sortition to avoid oligarchic influence over voters.