He sought to preserve his city's freedom and to establish an alliance against Macedon, in an unsuccessful attempt to impede Philip's plans to expand his influence southward, conquering the Greek states.

[29] According to Plutarch, when Demosthenes first addressed himself to the people, he was derided for his strange and uncouth style, "which was cumbered with long sentences and tortured with formal arguments to a most harsh and disagreeable excess".

[33] As a boy Demosthenes had a speech impairment: Plutarch refers to a weakness in his voice of "a perplexed and indistinct utterance and a shortness of breath, which, by breaking and disjointing his sentences much obscured the sense and meaning of what he spoke.

[34] Aeschines taunted him and referred to him in his speeches by the nickname "Batalus",[d] apparently invented by Demosthenes' pedagogues or by the little boys with whom he was playing[35]—which corresponded to how someone with that variety of rhotacism would pronounce "Battaros," the name of a legendary Libyan king who spoke quickly and in a disordered fashion.

[38] To make his living, Demosthenes became a professional litigant, both as a "logographer" (λογογράφος, logographos), writing speeches for use in private legal suits, and as an advocate (συνήγορος, sunégoros) speaking on another's behalf.

Logographers were a unique aspect of the Athenian justice system: evidence for a case was compiled by a magistrate in a preliminary hearing and litigants could present it as they pleased within set speeches; however, witnesses and documents were popularly mistrusted (since they could be secured by force or bribery), there was little cross-examination during the trial, there were no instructions to the jury from a judge, no conferencing between jurists before voting, the juries were huge (typically between 201 and 501 members), cases depended largely on questions of probable motive, and notions of natural justice were felt to take precedence over written law—conditions that favoured artfully constructed speeches.

It has often been argued that the deception, if there was one, involved a political quid pro quo, whereby Apollodorus secretly pledged support for unpopular reforms that Demosthenes was pursuing in the greater, public interest[44] (i.e. the diversion of Theoric Funds to military purposes).

[49] All these speeches, which offer early glimpses of his general principles on foreign policy, such as the importance of the navy, of alliances and of national honour,[50] are prosecutions (γραφὴ παρανόμων, graphē paranómōn) against individuals accused of illegally proposing legislative texts.

The rancorous and often hilariously exaggerated accusations, satirised by Old Comedy, were sustained by innuendo, inferences about motives, and a complete absence of proof; as J. H. Vince states "there was no room for chivalry in Athenian political life".

[53] Demosthenes was to become fully engaged in this kind of litigation and he was also to be instrumental in developing the power of the Areopagus to indict individuals for treason, invoked in the ekklesia by a process called ἀπόφασις (apóphasis).

In 351 BC, Demosthenes felt strong enough to express his view concerning the most important foreign policy issue facing Athens at that time: the stance his city should take towards Philip.

[50] Demosthenes saw the King of Macedon as a menace to the autonomy of all Greek cities and yet he presented him as a monster of Athens's own creation; in the First Philippic he reprimanded his fellow citizens as follows: "Even if something happens to him, you will soon raise up a second Philip [...]".

[71] In 348 BC a peculiar event occurred: Meidias, a wealthy Athenian, publicly slapped Demosthenes, who was at the time a choregos at the Greater Dionysia, a large religious festival in honour of the god Dionysus.

For Edmund M. Burke, this speech heralds a maturation in Demosthenes' career: after Philip's successful campaign in 346 BC, the Athenian statesman realised that, if he was to lead his city against the Macedonians, he had "to adjust his voice, to become less partisan in tone".

[91] When the Macedonian army approached Chersonese (now known as the Gallipoli Peninsula), an Athenian general named Diopeithes ravaged the maritime district of Thrace, thereby inciting Philip's rage.

However, the Athenian orator and statesman Demades is said to have remarked: "O King, when Fortune has cast you in the role of Agamemnon, are you not ashamed to act the part of Thersites [an obscene soldier of the Greek army during the Trojan War]?"

According to Aeschines, "it was but the seventh day after the death of his daughter, and though the ceremonies of mourning were not yet completed, he put a garland on his head and white raiment on his body, and there he stood making thank-offerings, violating all decency.

"[111] Mogens Hansen, however, notes that many Athenian leaders, Demosthenes included, made fortunes out of their political activism, especially by taking bribes from fellow citizens and such foreign states as Macedonia and Persia.

Given this pattern of corruption in Greek politics, it appears likely, writes Hansen, that Demosthenes accepted a huge bribe from Harpalus, and that he was justly found guilty in an Athenian People's Court.

Rebutting historian Theopompus, the biographer insists that for "the same party and post in politics which he held from the beginning, to these he kept constant to the end; and was so far from leaving them while he lived, that he chose rather to forsake his life than his purpose".

[123] According to Professor of Greek Arthur Wallace Pickarde, success may be a poor criterion for judging the actions of people like Demosthenes, who were motivated by the ideals of democracy political liberty.

[25] Most of his extant speeches for private cases—written early in his career—show glimpses of talent: a powerful intellectual drive, masterly selection (and omission) of facts, and a confident assertion of the justice of his case, all ensuring the dominance of his viewpoint over his rival.

[126] According to the classical scholar Harry Thurston Peck, Demosthenes "affects no learning; he aims at no elegance; he seeks no glaring ornaments; he rarely touches the heart with a soft or melting appeal, and when he does, it is only with an effect in which a third-rate speaker would have surpassed him.

I think there can hardly be found two other orators, who, from small and obscure beginnings, became so great and mighty; who both contested with kings and tyrants; both lost their daughters, were driven out of their country, and returned with honour; who, flying from thence again, were both seized upon by their enemies, and at last ended their lives with the liberty of their countrymen.During the Middle Ages and Renaissance, Demosthenes had a reputation for eloquence.

[158] The "publication" and distribution of prose texts was common practice in Athens by the latter half of the fourth century BC and Demosthenes was among the Athenian politicians who set the trend, publishing many or even all of his orations.

^ According to Edward Cohen, professor of Classics at the University of Pennsylvania, Cleoboule was the daughter of a Scythian woman and of an Athenian father, Gylon, although other scholars insist on the genealogical purity of Demosthenes.

[174] According to Aeschines, Gylon received as a gift from the Bosporan rulers a place called "the Gardens" in the colony of Kepoi in present-day Russia (located within two miles (3 km) of Phanagoria).

[5] Nevertheless, the accuracy of these allegations is disputed, since more than seventy years had elapsed between Gylon's possible treachery and Aeschines' speech, and, therefore, the orator could be confident that his audience would have no direct knowledge of events at Nymphaeum.

According to James J. Murphy, Professor emeritus of Rhetoric and Communication at the University of California, Davis, his lifelong career as a logographer continued even during his most intense involvement in the political struggle against Philip.

[50] E. M. Burke argues that, if this was indeed a law of Eubulus, it would have served "as a means to check a too-aggressive and expensive interventionism [...] allowing for the controlled expenditures on other items, including construction for defense".