Bust of Demosthenes, Roman copy after a Greek Hellenistic original; copy of Polyeuktos, c.a. 280 BC, via the British Museum.

When I was an undergraduate, one of my teachers used to talk only half-seriously about “Great Losers in American History,” beginning with Aaron Burr. It’s not a theme that George Patton would have warmed to. As the general said to the troops, “Americans love a winner and will not tolerate a loser.” No doubt that’s true—and not just in the U.S.—when it comes to choosing leaders. Yet even Americans evince a certain fascination for failure. Ahab or Gatsby or Willy Loman, anyone?

When the defeated goes down fighting, moreover, when he insists on the grandeur of his deeds or ideas, then he may even have a certain attraction that a winner lacks. A Francophile like Patton needed no introduction to the glamour of Napoleon. For that matter, I doubt if an orator of Patton’s caliber could have entirely resisted the glory of one of the charter members of any list of “Great Losers in Ancient History,” Demosthenes.

An Athenian statesman, Demosthenes (384–322 B.C.) devoted his career to convincing first his countrymen and then the rest of the Greeks to band together and fight the rising power first of Philip II of Macedon (382–336 B.C.) and then of his son Alexander the Great (356–323 B.C.). It was a grand effort and it failed. Macedon won; Athens and its allies lost.

Winston Churchill has often been held up as a modern Demosthenes and so he was, when it comes to speechmaking and statesmanship. There is, however, one big difference: Churchill won. There are other differences as well. Churchill was physically robust and the product of aristocratic self-confidence. Demosthenes was frail and famously overcame a speech defect to become a great orator. Moreover, neither Philip nor Alexander was Hitler. This means that the choices faced by Demosthenes do not seem as stark as those that faced Churchill. Yet the world sometimes ends not with a bang but a whimper, as the poet says. Not all enemies of freedom are monsters—sometimes they are even heroic in their own way. That makes it all the more important to understand Demosthenes and what he was fighting for.

Demosthenes lived long after Athens’ golden age of power and self-confidence, a period under Pericles (ca. 495–429 B.C.) that ended when Athens lost the Peloponnesian War in 404 B.C. The long cycle of wars among the Greek city-states left them all tired by the mid-fourth century B.C. Enter the vigorous, energized kingdom of Macedon, led by the dynamic and ruthless king Philip.

Nowadays Macedon is an integral part of the Greek nation, but in classical Greece the Macedonians were peripheral. The Macedonian elite spoke Greek as did many ordinary Macedonians, and they had much in common with their cousins to the south. There were, however, some big cultural and political differences. The main one was that Macedon was a kingdom while the states that had long dominated the Greek peninsula—Athens, Sparta, Thebes, and Corinth—were all city-states. They thought of Philip and his kingdom as outsiders and were not eager to be dominated by them.

By Demosthenes’ day, most Athenians preferred staying home and getting rich to chasing dragons abroad. They remained unconvinced for years that Philip represented a threat to their freedom and independence until finally the shadow of his growing power became obvious. Then they finally took Demosthenes’ advice, but it was too late. Philip conquered Greece. At the decisive Battle of Chaeronea (338 B.C.), 1,000 Athenians were killed and 2,000 made prisoners, out of an Athenian contingent in the Panhellenic army of 8,000 men (6,000 Athenian citzens and 2,000 mercenaries). Other Greek losses were also substantial.

Philip is said to have danced a drunken jig of joy after the battle to the zippy tune of Demosthenes’ full name in Athenian decrees: “De-mo-sthe-nes De-mo-sthe-nous Pai-a-neus,” that is, “Demosthenes, son of Demosthenes, of the county of Paiania.” Fortunately for Demosthenes, Philip proceeded to treat him and Athens relatively leniently. He made Athens give up most of its power abroad but left it alone at home. Philip needed Athens’ navy and its prestige for his upcoming war. In his mind, Greece was just the beginning. His real target was Persia. Persia ruled the largest empire the world had known to date. One man had founded it—Cyrus the Great (r. 559–530 B.C.). The empire was past its prime, and Philip believed that he was the one man who could grab it.

Shortly afterwards, Philip was assassinated and his son Alexander took the throne. Alexander the Great went on to fulfill Philip’s dream and conquer the Persian Empire. Alexander died young, however, and Demosthenes convinced the Athenians and a coalition of other Greeks to revolt. Once again, they lost. This time, the conquerors imposed harsh terms on Athens and demanded Demosthenes’ head. He fled and then took his own life.

It’s a sad story, or it might be, if that were all there was to it. But Demosthenes wasn’t just a great loser. He was a magnificent loser. He left behind a glorious body of oratory. A master speaker, Demosthenes provides one of history’s greatest examples of the art of persuading a free and democratic people.

Demosthenes’ speeches should be a part of everyone’s education. They are eloquent and powerful. They display a sophisticated, even breathtaking grasp of strategy, revealing the deep influence on him of Thucydides. Demosthenes’ description in “On the Crown” (330 B.C.) of the day he roused the Athenian assembly to action before Chaeronea is one of the most vivid and powerful pieces of political oratory ever written. He writes that, when the news came to the Athenian Assembly that Philip and his army had come south, the herald asked, as usual in that democratic body, “Who wishes to speak?” But no one came forward, not even the most prominent or accomplished. Demosthenes writes:

But, it seems, the call of the crisis on that momentous day was not only for the wealthy patriot but for the man who from first to last had closely watched the sequence of events, and had rightly fathomed the purposes and the desires of Philip; for anyone who had not grasped those purposes, or had not studied them long beforehand, however patriotic and however wealthy he might be, was not the man to appreciate the needs of the hour, or to find any counsel to offer to the people. On that day, then, the call was manifestly for me.

Demosthenes could be scathingly funny. He complained that the Athenians fought Philip the way a barbarian boxes. They never anticipated or parried a blow but only reacted when it was too late. He says:

You take your marching orders from him; you have never framed any plan of campaign for yourselves, never foreseen any event, until you learn that something has happened or is happening.

As Philip complained, Demosthenes’ speeches were soldiers. The king should have known: Demosthenes’ Philippics or speeches about Philip, have given the language a word for “violent denunciation.”

Demosthenes’ speeches are his finest legacy. They sizzle. His career, by contrast, was convoluted, at times humdrum, and sometimes ugly. Yet familiarity with his career is essential because it demonstrates what it takes to convince people that even a seductive threat to freedom is still a threat. The process is difficult and infuriating and it would drive the best of us half-mad, yet, somehow, Demosthenes did it.

To the benefit of readers, Ian Worthington has recently written a very fine introduction to Demosthenes’ career.1 He knows the subject well. As a classical scholar and historian, Worthington has written widely and with authority, including translations of Demosthenic speeches and a biography of Philip of Macedon. His is an erudite but readable biography of Demosthenes. It is sober, balanced, and analytical, which makes its bottom line all the more impressive.

Demosthenes was no saint. He could be petty and vindictive and he took bribes. To be sure, in Athens it was not a crime to take a bribe; it was only a crime to take a bribe and use the money against the best interests of the Athenian people. As Worthington demonstrates, Demosthenes was an opportunist. Then again, he was a politician. Politics isn’t philosophy. Demosthenes played rough but the game had rugged rules.

As Worthington argues, Demosthenes cannot be blamed for faulty strategy against Philip. Macedon was too strong, the Greek city-states too divided and worn out from their many wars. Demosthenes probably did the best anyone could have in trying to stop Philip. Philip was not to be appeased. He was brilliant, talented, power-hungry, and determined. He had money and resources. He was a smooth talker and a cunning diplomat. By reforming the old hoplite phalanx and adding Macedon’s traditional strength in cavalry, Philip created a combined-arms military that was all but unbeatable in battle. To this he added the Greek world’s latest scientific advances in siege warfare. He was a powerful warrior.

By the same token, Philip was no monster. He unified Greece—something that won him the admiration of many a scholar in the nineteenth century during the glory days of national liberation and unification. Philip admired the culture of the Greek city-states and had no intention of destroying it or ruining them. He wanted to curtail their independence sharply and subject them to Macedonian rule. In the short run, they lost the freedom to make their own foreign policy. In the long run, Macedon’s influence went deeper and was more insidious.

Philip no doubt believed sincerely that Greece could be prosperous and cultivated under Macedonian leadership. Perhaps he was already thinking of the spread of Greek culture in the former Persian Empire that took place in the years after Alexander’s conquests (in some ways more a byproduct than a conscious policy). But what couldn’t endure the Macedonian conquest was the Greek culture of freedom and independence.

Courtiers often live good lives, and surely more glamorous lives than do the citizens of republics, but they lack the simple freedom of a citizen, the freedom to say what they think, the freedom to say no. Demosthenes knew that Philip’s friends lived comfortably, and Athens under Macedon might have been even happier than it was in its own cantankerous independence. It would never be free, though, and without freedom there could be no failure, and without failure, there could be no tragedy—that most profound product of the ancient Greek soul.

Philip was no democrat which meant that there could be no democracy either. Once he controlled Greece, he or his successors would eventually find it easier to deal with Athenian oligarchs than with Athenian democrats. There were indeed oligarchs in Athens and their numbers were likely to grow with the power of Macedon. Demosthenes knew all this.

Demosthenes failed but he bought time for democracy. He died in 322 B.C. but Athenian democracy survived at least for another sixty years, albeit with short intervals of Macedonian-imposed oligarchy. If the Athenians had simply rolled over in the face of Philip without fighting, the pro-Macedonian party would have come to power much sooner in Athens and weakened democracy from within. Thanks to Demosthenes, Athens went down fighting, and it kept fighting for generations longer than it might have otherwise. Athenians knew it and they honored his memory.

Worthington quotes the Athenian decree establishing posthumous public honors for Demosthenes and privileges for his descendants. The text resolves that Demosthenes “performed the best public actions in the cause of liberty and democracy.”

Worthington understands the case against Demosthenes. He looks down wryly on the abuse of Demosthenes’ name by various politicians who have appropriated it. But his balanced and reasoned argument makes the case for Demosthenes’ shining legacy:

in our world of ordinary people standing boldly, defiantly and bravely against tyrannies and totalitarian regimes, one cannot help but liken some of them to Demosthenes.

That’s what it comes down to in the end. That “great loser,” Demosthenes, fought for freedom and failed. Yet his words remind us what the fight is for and his deeds show us that although those who fight it may lose, they are no losers.

1Demosthenes of Athens and the Fall of Classical Greece, by Ian Worthington; Oxford University Press, 416 pages, $35.

This article originally appeared in The New Criterion, Volume 31 Number 7, on page 14
Copyright © 2020 The New Criterion | www.newcriterion.com

Popular Right Now