What is the Battle of Chaeronea, 338 BC?

§-Syllabus dot point

NSWAncient HistorySyllabus dot point

How did Philip II bring the Greek states under Macedonian control at Chaeronea and through the League of Corinth, and how did the period end with his assassination and the accession of Alexander?

The final confrontation and settlement of Greece: Demosthenes and the Athenian-Theban alliance against Philip II; the decisive Macedonian victory at the Battle of Chaeronea in 338 BC and the destruction of the Theban Sacred Band by the cavalry of the eighteen-year-old Alexander; the League of Corinth of 337 BC, a common peace under Macedonian hegemony with garrisons at key points and Sparta alone excluded; the proclamation of the panhellenic war of revenge against Persia with Philip as hegemon; and Philip's assassination at Aegae in 336 BC and the accession of Alexander, which closes the period on the threshold of the Hellenistic age

The final act of the period - Demosthenes builds an Athenian-Theban alliance, Philip II wins the decisive Battle of Chaeronea in 338 BC with the young Alexander breaking the Theban Sacred Band, the League of Corinth of 337 BC binds Greece under Macedonian hegemony for a war on Persia, and Philip is assassinated at Aegae in 336 BC.

Generated by Claude Opus 4.813 min answerUpdated 2026-07-01

Reviewed by: AI editorial process; not yet individually human-reviewed

Have a quick question? Jump to the Q&A page

Quick answer

The period closes with the triumph of Macedon. Demosthenes overcame the old enmity of Athens and Thebes to build an alliance against Philip II (339 BC), but at Chaeronea (338 BC) Philip won decisively, the eighteen-year-old Alexander leading the cavalry that destroyed the Theban Sacred Band, whose 300 fell where they stood (later marked by the Lion of Chaeronea). Philip then organised the League of Corinth (337 BC), a common peace under his hegemony, with a council (the synedrion), garrisons at the Cadmea and the Acrocorinth, and Sparta alone excluded; the League declared a panhellenic war of revenge on Persia with Philip as leader, and an advance force under Parmenion and Attalus crossed to Asia in 336 BC. Before he could follow, Philip was assassinated at Aegae by Pausanias of Orestis (336 BC), and Alexander succeeded to throne, army, League and war. Our evidence is the contemporary but partisan oratory of Demosthenes set against the late narratives of Diodorus (Book 16), Plutarch and Justin; historians such as Hammond and Worthington read Philip as the true architect of Macedonian supremacy who ended Greek freedom in substance while leaving its forms intact, closing the classical age on the threshold of the Hellenistic.

Jump to a section

What this dot point is asking
The answer
How to read a source on this topic

What this dot point is asking

This is the closing slice of the period "Greece from 404 BC to the death of Philip II," and it asks you to explain how the long story of fourth-century rivalry ended in the triumph of Macedon. You need the final confrontation: how Demosthenes overcame the old enmity between Athens and Thebes to build an alliance against Philip II. You need the Battle of Chaeronea (338 BC) itself, Philip's decisive victory, the eighteen-year-old Alexander commanding the cavalry that broke the Theban Sacred Band. You need the settlement that followed, the League of Corinth (337 BC), a common peace under Macedonian hegemony with garrisons at key points and Sparta alone excluded, and the panhellenic war of revenge against Persia proclaimed with Philip as its leader. Finally you need the end of the period itself: Philip's assassination at Aegae in 336 BC and the succession of Alexander, the point at which the classical Greek world gives way to the Hellenistic age. This dot point is analytical, not just narrative: it wants you to weigh how far Chaeronea and the League ended Greek freedom.

In plain English

Picture a neighbourhood that has spent years feuding, until a bigger, tougher outsider starts buying up every street. Two of the oldest rivals on the block, Athens and Thebes, finally stop fighting each other and team up, talked into it by a fierce local campaigner named Demosthenes. They make their stand at a place called Chaeronea in 338 BC and lose badly, and it is the outsider's teenage son, Alexander, who leads the charge that smashes the toughest gang in the fight, Thebes' famous 300. Instead of bulldozing the neighbourhood, the winner, Philip, sets up a residents' association where everyone is "free" but he is permanent chairman, keeps guards on the key corners, and announces that they are all going to go and rob the rich empire next door, Persia. Then, at a family wedding, Philip is stabbed to death by one of his own bodyguards, and the whole plan passes to that teenage son. That is where the story ends and Alexander's begins.

The answer

Demosthenes and the making of the Athenian-Theban alliance

Through the 340s BC the Athenian orator Demosthenes had been the most determined voice against Philip. In a series of speeches, the Philippics and the Olynthiacs, he argued that Philip's steady expansion into the north and into central Greece was not a distant nuisance but a mortal threat to the freedom of the Greek cities, and that Athens must arm and resist rather than trust to negotiation. His achievement was as much diplomatic as rhetorical. When Philip seized Elatea in 339 BC and stood poised to strike into central Greece, the danger was acute, and Demosthenes crossed to Thebes and helped to overcome the long, bitter hostility between Athens and Thebes to bring the two greatest land and naval powers of the south into a single alliance. That coalition, joined by other states, was the army that would face Philip at Chaeronea. Demosthenes never repudiated this policy: even after the defeat, in his great speech On the Crown (330 BC), delivered against his rival Aeschines, he defended resistance to Philip as the honourable course that Athens' history demanded, whatever fortune had decreed.

The Battle of Chaeronea, 338 BC

The armies met in 338 BC on the plain of Chaeronea in Boeotia. Our fullest account is that of Diodorus Siculus (Book 16). Philip commanded the Macedonian right wing, drawn up opposite the Athenians; his eighteen-year-old son Alexander led the cavalry on the left, facing the Thebans and, on the extreme allied right, their elite Sacred Band. The decisive stroke, as the tradition tells it, was a calculated one: Philip drew the eager Athenians forward on his wing, so opening a gap in the allied line, and through that gap Alexander charged, shattering the Theban wing. The allied army broke and fled, Demosthenes among the fugitives. The Sacred Band, the 300 picked Theban hoplites who had been the terror of the battlefield since the days of Leuctra, refused to run and fell where they stood. Plutarch records that Philip, surveying their bodies where they lay in their ranks, was moved to tears. Their common grave was later marked by the Lion of Chaeronea, a great stone lion that still stands. Chaeronea ended the capacity of the Greek states to resist Philip in the field.

The settlement of Greece and the League of Corinth, 337 BC

Philip's treatment of the defeated was shrewdly measured. Thebes, which had broken its alliance with him, was punished: a Macedonian garrison was installed in its citadel, the Cadmea, and its control of Boeotia was stripped away. Athens, by contrast, braced for the worst but was treated with striking leniency: Philip returned its prisoners without ransom, did not march on the city, and left its democracy standing, though Athens had to give up the last remnants of its naval confederacy. Then, in 337 BC, Philip called delegates of the Greek states to Corinth and organised them into what we call the League of Corinth (the Hellenic League). This was a common peace (koine eirene): the member states were declared free and autonomous, sworn not to make war on one another, not to overthrow existing constitutions by force, and to uphold the settlement and the position of Philip and his descendants. A standing council, the synedrion, represented the members, but Philip himself was hegemon, the leader, with the real power. Macedonian garrisons at strategic points, above all the Cadmea at Thebes and the Acrocorinth at Corinth, ensured that "freedom" operated within limits Philip set. Sparta alone refused to take part and was left outside the League, a defiant but now marginal exception. The genius of the arrangement was that it secured Macedonian mastery of Greece while leaving the cities the outward forms of independence.

The panhellenic war of revenge against Persia

The League was not merely a peace; it was the instrument of Philip's greatest ambition. Its council duly declared a panhellenic war against Persia and appointed Philip its commander. The war was framed not as a Macedonian conquest but as a shared Greek crusade of revenge for the Persian invasions of Xerxes a century and a half earlier, an idea long urged by the aged Athenian pamphleteer Isocrates, who had argued that a united Greece should turn its energies outward against the common barbarian foe. By clothing his invasion in this panhellenic dress, Philip gave it legitimacy and bound the Greek states to supply contingents for it. In 336 BC he sent an advance force under his generals Parmenion and Attalus across into Asia Minor to prepare the ground. The main expedition, and Philip himself, were to follow.

The assassination of Philip at Aegae, 336 BC, and the accession of Alexander

Philip never crossed to Asia. In 336 BC, at the old royal centre of Aegae (modern Vergina), he held a great festival to celebrate the marriage of his daughter Cleopatra to Alexander of Epirus. As he entered the theatre, deliberately walking ahead of his guards to display his confidence before an audience of Greeks, he was struck down and killed by Pausanias of Orestis, a member of his own bodyguard, who was cut down by other guards as he tried to flee. The murder's motive is given by the sources as a bitter personal grievance, but ancient rumour, reported most fully in Justin, hinted at a wider conspiracy reaching to Philip's estranged queen Olympias or even to Alexander; the evidence is late and coloured by hindsight, and most modern historians treat any such conspiracy as unproven. What is certain is the result. The throne, the transformed Macedonian army, the mastery of Greece embodied in the League of Corinth, and the war against Persia all passed at once to Philip's son, the twenty-year-old Alexander. The death of Philip closes the period "Greece from 404 BC to the death of Philip II," and stands on the threshold of the Hellenistic age that Alexander's conquests would open.

How to read a source on this topic

Sources for this dot point fall into two very different kinds, and telling them apart is half the skill. First, there is contemporary evidence, above all the speeches of Demosthenes (the Philippics; On the Crown of 330 BC) and of his rival Aeschines. These are gold because they are firsthand and from the heart of events, but they are political oratory, not history: Demosthenes is defending his own record and paints Philip as a tyrant and himself as the champion of freedom, so his perspective must always be weighed. Second, there is the later narrative tradition, chiefly Diodorus Siculus (Book 16, mid first century BC), Plutarch (Life of Demosthenes, Life of Alexander, and the Life of Pelopidas for the Sacred Band), and the epitome of Justin (from Pompeius Trogus). These give the connected story of Chaeronea, the League and the assassination, but they were written 300 years or more later, are derivative, and are prone to drama and moralising.

So the reading habits are: place the source in time (is it contemporary oratory or a late narrative?); fix its purpose and bias (self-justification in Demosthenes; a taste for the dramatic and the moralising point in Diodorus, Plutarch and Justin, especially on the murder); and move from content to reliability to usefulness to perspective before reaching a judgement. On this topic that almost always means testing the partisan contemporary voice of Demosthenes against the late narrative of Diodorus, and treating the conspiracy rumours around Philip's death with particular caution.

Historians and interpretations

The ancient picture is dominated by Demosthenes' own version of events, in which resistance to Philip was the noble defence of Greek freedom; the later writers Diodorus, Plutarch and Justin transmit and dramatise the story. Modern historians read Philip's achievement in strongly differing lights. N.G.L. Hammond presented Philip as a statesman of the first rank, the true architect of Macedonian greatness, whose settlement of Greece and panhellenic war were the deliberate foundation on which Alexander built. Ian Worthington, in studies of both Philip and Demosthenes, likewise stresses Philip as the real founder of Macedonian power, and reads the League of Corinth as a masterstroke that secured genuine control while preserving the appearance of freedom; he is correspondingly sceptical of Demosthenes' heroic self-image. G.L. Cawkwell and J.R. Ellis similarly emphasise the calculation behind Philip's leniency and his settlement. On the assassination there is real division: some have been willing to entertain the ancient rumour, reported in Justin, of the involvement of Olympias or Alexander, but most, mindful that the evidence is late and shaped by later dynastic hostilities, regard the conspiracy theories as unproven and prefer the sources' plain account of a personal grievance. Use these interpretations to qualify your argument, not as decoration.

Model exam responses

1. Source-analysis response (using a described passage of Demosthenes). "A described passage of Demosthenes' On the Crown is valuable because it is contemporary and by the central figure of the Greek resistance, giving direct evidence of how Athens argued and felt about the struggle with Philip. Its reliability, however, is limited by its purpose: the speech was delivered in 330 BC to defend Demosthenes against Aeschines, so it flatters his own policy, presents resistance at Chaeronea as honourable, and blames the defeat on fortune rather than on his advice. The passage is therefore most useful as evidence for the Athenian case and mood, and for the politics of resistance, but on Philip's aims and on the wisdom of the war it must be tested against the later narrative of Diodorus and against Philip's own moderate treatment of Athens after the battle."

Marker's note: markers reward identifying the source as contemporary but partisan oratory, an explicit usefulness/perspective split, and corroboration against other evidence rather than paraphrase.

2. Essay paragraph (the League ended freedom in substance, not in form). "The victory at Chaeronea was completed by a settlement that ended Greek freedom in substance while carefully preserving its forms. Through the League of Corinth of 337 BC Philip left the cities 'free and autonomous' and gave them a council, the synedrion, yet made himself hegemon, placed garrisons in the Cadmea and the Acrocorinth, and bound the members to a Persian war of his own devising. As Worthington argues, Philip's real achievement was to secure genuine Macedonian control behind a facade of independence, which is precisely why Demosthenes could still invoke the language of liberty even after the power to act on it had gone. The freedom of the city-states did not so much end at Chaeronea as become a memory the Greeks honoured while obeying a king."

Marker's note: this paragraph scores because it distinguishes the form from the reality of freedom, uses precise detail (synedrion, the garrisons, the dates) and deploys a named historian to build the argument.

Command words and how to use a source

Outline/describe wants a small number of clearly separated points; explain wants a point, evidence and why it matters; assess/evaluate/to what extent wants a sustained argument reaching a supported judgement, which is the usual Section IV essay mode.

Using a source properly means four moves every time: (1) content, what does it actually show; (2) reliability, who produced it, when and for what purpose; (3) usefulness, what specific question can it help answer, and how far; (4) perspective, whose viewpoint is it, and what does it leave out. For this topic, always ask first whether a source is contemporary oratory (Demosthenes, Aeschines) or a late narrative (Diodorus, Plutarch, Justin), because that usually decides its value.

Weaving in historiography means using a historian's named position to sharpen a claim, for example "as Worthington argues, the League secured real control behind a facade of freedom," attached to a specific point rather than dropped in as a label.

Common exam traps

Retelling the battle instead of arguing its significance: A Section IV essay rewards analysis. Do not narrate Chaeronea blow by blow; use it as evidence for a point about the end of Greek independence or the rise of Macedon.
Crediting Alexander with the victory alone: The strategy, the army and the settlement were Philip's; Alexander commanded one wing at Chaeronea. Give Philip his due as the architect, as Hammond and Worthington insist.
Treating the League as genuine freedom, or as simple annexation: It was neither. The cities kept the forms of autonomy but lost real independence, held by garrisons under a Macedonian hegemon. Missing this nuance weakens the argument.
Stating the assassination conspiracy as fact: That Olympias or Alexander plotted Philip's death is late rumour (Justin), not established fact. Report it as an unproven tradition and note the sources' account of a personal grievance.
Confusing the sources: Demosthenes is a contemporary but partisan orator; Diodorus, Plutarch and Justin are late narratives. Do not treat any of them as a neutral eyewitness record.

Practice questions

Original practice questions graded from foundation to exam level, each with a full worked solution. Try them before revealing the solution.

foundation3 marksSource A: a reconstructed oath of this type, written in the style of the surviving oath sworn by the Greek states to the League of Corinth, records that the swearers will keep the common peace, will not overthrow the kingship of Philip or of his descendants, and will march against any state that breaks the agreement, under the leadership of the appointed hegemon. Using Source A, describe what it reveals about Philip II's settlement of Greece in 337 BC.

Show worked solution →

A 3-mark "describe" needs what the record is, what it shows about Philip's settlement, and one supporting detail.

What the record is: Source A reflects the founding oath of the League of Corinth (the Hellenic League), the common peace (koine eirene) Philip organised in 337 BC after his victory at Chaeronea, binding the Greek states under his leadership as hegemon (1 mark).
What it reveals: It shows that Philip controlled Greece not by outright annexation but by making the states swear a common peace that froze the political order and protected his own supremacy, so that Macedonian hegemony was dressed as a shared Greek agreement (1 mark).
Supporting detail: The clause guaranteeing "the kingship of Philip and of his descendants" shows the settlement was designed to be permanent and dynastic, obliging the Greeks to defend Macedonian rule rather than merely to keep peace among themselves (1 mark).

Marker's note: markers reward direct use of the source's own detail (common peace, a hegemon, protection of Philip's house) rather than a general account of Philip's reign.

foundation4 marksOutline the course and outcome of the Battle of Chaeronea in 338 BC.

Show worked solution →

A 4-mark "outline" needs who fought, the key tactical move, the outcome and its significance.

The armies: In 338 BC Philip II met the allied army of Athens, Thebes and their partners on the plain of Chaeronea in Boeotia. Philip commanded the Macedonian right; his eighteen-year-old son Alexander led the cavalry on the left, opposite the Thebans and their elite Sacred Band (1 mark).
The decisive move: According to Diodorus (Book 16), Philip drew the Athenians forward on his right, opening a gap in the allied line, through which Alexander charged and broke the Theban wing (1 mark).
The outcome: The allied army was routed; the 300 of the Theban Sacred Band fell where they stood, later commemorated by the Lion of Chaeronea monument (1 mark).
Significance: The victory ended organised Greek resistance and left Philip master of Greece, opening the way to the League of Corinth (1 mark).

Marker's note: markers reward Alexander's role and the destruction of the Sacred Band, not a vague statement that Philip "won a battle."

foundation4 marksOutline the nature and terms of the League of Corinth established by Philip II in 337 BC.

Show worked solution →

A 4-mark "outline" needs the League's form, its terms, its enforcement and who stood outside it.

Form: In 337 BC Philip organised the defeated Greek states into the League of Corinth (the Hellenic League), a common peace (koine eirene) of nominally free and autonomous states with himself as leader (hegemon), governed through a council of delegates (the synedrion) (1 mark).
Terms: Members swore to keep the peace, not to change existing constitutions by force, not to attack one another, and to protect the settlement and the position of Philip and his house (1 mark).
Enforcement: Macedonian garrisons were placed at key points, such as the Cadmea in Thebes and the Acrocorinth at Corinth, so the "free" states were held under Macedonian supervision (1 mark).
Who stood outside: Sparta alone refused to join and was left excluded, a proud but now powerless exception (1 mark).

Marker's note: markers reward the hegemon/synedrion structure and the garrisons, and credit the point that autonomy was largely a fiction.

core6 marksExplain the part played by Demosthenes in the confrontation between the Greek states and Philip II that led to Chaeronea.

Show worked solution →

A 6-mark "explain" needs Demosthenes' policy, his key achievement, and how it led to the battle, each tied to evidence.

His policy: The Athenian orator Demosthenes was the leading voice against Philip. In his Philippics and Olynthiacs through the 340s BC he warned that Philip's expansion threatened Greek freedom and urged Athens to resist rather than negotiate (2 marks).
His key achievement: His greatest success was diplomatic: in 339 BC, when Philip advanced into central Greece, Demosthenes helped to overcome the long hostility between Athens and Thebes and forge an alliance between the two cities, bringing Thebes into the field against Philip (2 marks).
How it led to Chaeronea: This coalition met Philip at Chaeronea in 338 BC. Its defeat vindicated Philip's power, but Demosthenes never accepted that his policy was wrong: in his later speech On the Crown he defended resistance as the honourable course, whatever the outcome (2 marks).

Marker's note: markers reward the specific achievement of the Athenian-Theban alliance and use of Demosthenes' own speeches, not a general claim that he "opposed Philip."

core6 marksSource B: a reconstructed passage of this type, in the style of Demosthenes' speech On the Crown, defends the speaker's policy of resisting Philip, insists that Athens acted honourably in defending Greek freedom, and blames the defeat on fortune rather than on his own advice. Using Source B and your own knowledge, explain how useful this kind of source is for the historian of Philip's conquest of Greece.

Show worked solution →

A 6-mark "explain" needs use of the source, its value, and its limits as evidence.

Use of the source: Source B reflects Demosthenes' self-justifying manner in On the Crown, delivered in 330 BC, where he defends his anti-Macedonian policy and recasts the disaster at Chaeronea as honourable resistance undone by fortune (2 marks).
Its value: A source of this kind is highly valuable because it is contemporary and by a central participant, giving direct insight into the arguments, mood and politics of the Greek resistance, and into how Athens understood its own struggle against Philip (2 marks).
Its limits: But it is a partisan courtroom speech, not a balanced history: Demosthenes is defending himself against Aeschines, so he flatters his own policy, blames fortune and paints Philip as a tyrant. It must be tested against Diodorus and against Philip's actual moderate settlement of Athens (2 marks).

Marker's note: markers reward the reliability/perspective split, the point that it is contemporary but partisan, and corroboration against other evidence rather than description alone.

core6 marksExplain the significance of the League of Corinth for Macedonian control of Greece.

Show worked solution →

A 6-mark "explain" needs what the League did, why it was effective, and its wider purpose.

What it did: The League of Corinth (337 BC) bound the Greek states into a common peace under Philip as hegemon, forbidding them to make war on one another or to change their constitutions by force, and it committed them to supply troops for a common cause (2 marks).
Why it was effective: By leaving the cities nominally free and autonomous while placing garrisons at strategic points such as the Cadmea and the Acrocorinth, Philip secured control without the cost and resentment of direct annexation, and made the Greeks themselves guarantors of the settlement (2 marks).
Its wider purpose: The League gave Philip a legitimate, panhellenic framework for the invasion of Persia: the war of revenge could be declared as a shared Greek enterprise led by its hegemon, not a naked Macedonian conquest, and Alexander would inherit both the League and the war (2 marks).

Marker's note: markers reward the causal link from a "free" but garrisoned Greece to a legitimised Persian war, not a mere description of the League's clauses.

exam8 marksAssess the value and limitations of Diodorus Siculus as a source for the Battle of Chaeronea and Philip's settlement of Greece.

Show worked solution →

An 8-mark "assess" answer needs the nature of the source, its value, its limitations and a judgement.

Nature: Diodorus Siculus wrote his universal history, the Bibliotheke, in the mid first century BC, roughly 300 years after Philip. Book 16 covers Philip's reign, and provides our fullest surviving connected narrative of Chaeronea and the League of Corinth (2 marks).
Value: Diodorus preserves detail found nowhere else, including the disposition of the armies at Chaeronea and Alexander's role in breaking the Theban line, and he drew on earlier writers now lost, such as Ephorus and Diyllus. For the events themselves he is often the historian's starting point (2 marks).
Limitations: He is late and derivative, compiling rather than researching, and he is uneven and sometimes muddled in chronology and numbers. He depends on the quality of his lost sources, and his taste for dramatic and moralising set-pieces, in the manner of the later tradition, means his detail must be handled critically (2 marks).
Judgement: Diodorus is indispensable because he alone gives a continuous narrative of Chaeronea and the settlement, but his lateness, dependence on lost sources and uneven method mean he is most reliable where he can be checked against contemporary evidence such as Demosthenes and Aeschines, and against the epitome of Justin (2 marks).

Marker's note: markers reward weighing Diodorus' unique narrative value against his lateness and compiling method, and reaching a supported judgement rather than dismissing or trusting him wholesale.

exam25 marksTo what extent did the Battle of Chaeronea and the League of Corinth mark the end of Greek freedom? In your response, refer to relevant sources and historians' interpretations.

Show worked solution →

A Band-6 response needs a clear thesis, argument lines tied to specific events, dates and sources, engagement with historiography, a model paragraph and a judgement answering "to what extent."

Thesis: Chaeronea (338 BC) and the League of Corinth (337 BC) largely ended the independence of the Greek city-states as a political reality, subordinating them to Macedonian hegemony; yet the forms of freedom survived, and the true end of the classical order came less as a single event than as a process that the assassination of Philip and the accession of Alexander then carried into a new, Hellenistic age.
Argument 1: militarily, Chaeronea was decisive: The defeat of the Athenian-Theban alliance in 338 BC broke the last serious coalition capable of resisting Macedon. The 300 of the Sacred Band fell where they stood, and, as Diodorus (Book 16) records, no Greek army again met Philip in the open field. Thereafter the balance of power lay permanently with the Macedonian king.
Argument 2: the League institutionalised subordination: The League of Corinth (337 BC) made the cities swear a common peace that froze their constitutions, forbade war between them, and protected the position of Philip and his house, while garrisons held the Cadmea and the Acrocorinth. The states remained nominally free and autonomous, but their freedom of action in war and alliance was gone.
Argument 3: but the forms and the ideal survived: Athens kept its democracy and was treated with striking leniency, and Demosthenes could still, in On the Crown (330 BC), defend resistance as honourable. Sparta's proud exclusion showed that Macedonian control was not total. The language of freedom persisted, and would be invoked again in the revolts after Alexander's death.
Argument 4: historians read the change differently: N.G.L. Hammond and Ian Worthington see Philip as the true architect of a new order, with Chaeronea and the League as the deliberate foundation of Macedonian supremacy that Alexander inherited. Others stress that the city-state was not abolished but absorbed, its autonomy hollowed rather than ended, so that 338 BC marks a transformation more than a simple extinction of freedom.
Model paragraph: The clearest measure of the change is the gap between form and reality after 338 BC. On paper the League of Corinth was an alliance of free and autonomous Greek states meeting in a common council; in practice its hegemon was a foreign king whose garrisons sat in the citadels of its members and whose war on Persia the cities were bound to support. As Worthington argues, Philip's genius was to secure real control while leaving the appearance of freedom intact, which is why Demosthenes could still speak the language of liberty even as the power to act on it had passed to Macedon. Greek freedom did not so much end in a day as become a memory the cities honoured while obeying a king.
Judgement: To a large extent Chaeronea and the League ended Greek freedom as an effective political reality, for after 338 BC no city could pursue an independent foreign policy against Macedon; but not wholly, since the institutions, the democratic forms and the ideal of eleutheria survived, and it was Philip's murder in 336 BC and Alexander's succession that turned this Macedonian hegemony over Greece into the launching-point of the Hellenistic world.

Marker's note: markers reward a sustained argument answering "to what extent," precise use of dated events and named sources (Diodorus, Demosthenes), historians used to build the case (Hammond, Worthington), and a distinction between the form and the reality of freedom.