Harpalus (Greek: Ἅρπαλος) son of Machatas was an aristocrat of Macedon and boyhood friend of Alexander the Great in the 4th century BC. Being lame in a leg, and therefore exempt from military service, Harpalus did not follow Alexander in his advance within the Persian Empire but received nonetheless a post in Asia Minor. Alexander reportedly contacted him with a demand of reading material for his spare time. Harpalus sent his King theatrical plays by Aeschylus, Sophocles and Euripides, the history of Philistus and odes by Philoxenus and Telestes.
Harpalus was also a charming rogue who absconded three times with large amounts of money. The first time he was forgiven and reinstated, only to abuse his trust again. In 324 BC Harpalus found refuge in Athens. He was imprisoned by the Athenians after a proposal of Demosthenes and Phocion, despite Hypereides' opposition, who wanted an immediate uprising against Alexander. The Ecclesia, based on a proposal from Demosthenes, decided on the guarding of Harpalus' money, which was entrusted to a committee led by Demosthenes himself. When the committee counted the money they found 350 talents, although Harpalus had declared that he had 700 talents. Nevertheless, Demosthenes and the other members of the committee decided not to disclose the deficit.
When Harpalus escaped and fled to Crete, the orator faced a new wave of public uproar. The Areopagus conducted an inquiry and its findings led to Demosthenes being charged with mishandling 20 talents. At Demosthenes' trial in the Heliaia, Hypereides, who was the main prosecutor, noted that Demosthenes had admitted taking the money, but said that he had used it on the people's behalf and had borrowed it free of interest. The prosecutor rejected this argument and accused Demosthenes of being bribed by Alexander. Demosthenes was fined 50 talents and imprisoned, but after a few days he escaped thanks to the carelessness or connivance of some citizens and travelled around Calauria, Aegina and Troezen. It remains still unclear whether the accusations against him were just or not. In any case, the Athenians soon repealed the sentence and sent a ship to Aegina to carry Demosthenes back to the port of Piraeus.