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I explore how and why Demosthenes uses money in his rhetoric to characterise Philip of Macedon negatively. The public speeches of Demosthenes from the 340s make frequent reference to the limited resources that are readily available to the Athenian state. The orator frequently exhorts his audience to neglect no longer their financial duties and so to allow the polis to wage war effectively. The rich are to pay contributions and the dêmos as a whole has to vote its generals enough money to carry out their mandates. It is the worsening threat of Philip II of Macedon which makes this expenditure necessary. Demosthenes’ handling of financial matters in his speeches is increasingly being studied in its own right (i.e. Harris 1996; Burke 2002). Demosthenes’ financial rhetoric does in fact do more than persuade the Athenians to rectify their situation. He characterises the conflict between Athens and Philip using the oppositions of democracy and tyranny, and, to a lesser extent, that between Greek and non-Greek, and even between the character of Philip and himself. The importance of money in conceptualising this conflict or, more precisely, the importance of financial organisation, has not been recognised. It underlies all of Demosthenes’ rhetoric against Philip and frequently reveals itself in some of his most forceful passages. I focus chiefly on the Olynthiacs and Philippics to show, first, that Demosthenes presents Philip’s relationship with money in such a way as to denigrate him and to rouse the Athenians against him. The most common attributes of Philip are his guile, rapaciousness, and omnipresence. Philip advances himself by deceitful exchanges, by seizing the wealth of others, and by bribing the Greeks to obey him. He is never said to have the regular revenues of a state such as mineral resources or taxes at his disposal. Indeed, Demosthenes says the Athenians are not fighting a polis but one man (Dem.9.72). This is less a dilemma about how to characterise the Macedonian national state, I argue, than a deliberate rhetorical strategy. In Athenian eyes, Philip’s monetary behaviour is key to the way Demosthenes configures him as deceptive, mercenary, and immoral. He is less tyrant than paymaster and pirate, a new and sinister Other whose growth must be resisted like a contagion (9.39). This is in stark contrast to the Athenian polis state, which I analyse in the second half of the paper. Demosthenes’ strictures about the performance of duty serve to play up the extent to which Athenians manage money through open political institutions and a complex financial organisation. Unlike Philip, the Athenians fight openly, and morally, by investing money in their army instead of bribing others not to fight (9.48-9). Unlike Philip, Athenian power is secure because it is based on their own prosperous homeland with its farms, docks, and mines (14.30; 8.44-5). Demosthenes therefore exaggerates the way in which Philip does not conform to long-established Athenian ideologies of money in terms of its moral use and its role in expressing military power (Kallet-Marx 1993; Kallet 2001). He does so in order to persuade a reluctant Athenian public of both the necessity of resisting Philip and the near-certainty of success if they do. I conclude by showing how, in the process, Demosthenes undercuts himself. First, he disseminates an inaccurate vision of Philip’s true strength. Second, the way Demosthenes emphasises the economic centrality of Attica to Athens, while helpfully characterising Athens as the enemy of Macedonian imperialism, weakens his repeated calls for greater interventionism abroad. In Demosthenes’ use of public money as an indicator of deeper moral and political realities, we have a rhetoric which masterfully exploits the perceptions of its audience. It is also, however, a rhetoric constrained by these perceptions in its all-important task of helping Athenians respond to a serious new danger.