Chares was a competent but reckless Athenian general during the thirty years before the rise of Alexander the Great, and who gained a reputation for being unusually greedy and corrupt. The length of his military career was probably due to a combination of his alliance with Demosthenes and a lack of more successful rivals at Athens.
Chares first appears in 367 BC, during the Wars of the Theban Hegemony. He was sent to help the people of Phlius (an inland city in the Argolid in the north-east of the Peloponnese, who were under pressure from the Arcadians to the west, the Argives to the east and the Theban garrison of Sicyon to their north. Chares escorted a supply convoy from Corinth to Phlius, and then helped escort the non-combatants as they were evacuated to Pellene. Chares won two battles against the Argives and lifted the pressure on Phlius.
After successfully defending Phlius, Chares was sent to Oropus, in the north-west of Attica, which had recently been captured by a group of anti-Athenian exiles who now supported the Thebans. Chares was summoned to command the Athenian army that was sent to retake Oropus, but no Athenian allies joined the army, and the expedition was abandoned.
In 361, after the end of the Theban wars, Chares succeeded Leosthenes, who had been defeated by Alexander of Pherae during an Athenian attempt to help Peparethos, on the island of Skopelos, to the north of Euboea. Chares ignored the fighting in the Aegean, and instead sailed around to Corcyra on Corfu, where he became involved in an oligarchic conspiracy that resulted in the fall of the local democracy. This soon backfired on Athens - the oligarchs remained hostile to Athens, and the democrats became hostile. Chares's actions effectively saw Corcyra leave the Second Athenian League and also worried her other allies. When Athens's allies rebelled against her, triggering the Social War, Corcyra joined the revolt.
In 358 Chares was sent to Thrace. He forced Charidemus, then the power behind the throne of Cersobleptes, king of Thrace, to ratify the treaty he had agreed with Athenodorus, in which the Chersoneses was given to Athens. This was a key area for Athens, as possession of harbours on the Chersoneses helped to secure their grain routes to the Black Sea. Despite the important of the area, the Athenians don't appear to have taken possession of the area until 353 BC.
In 357 Chios, Rhodes and Byzantium rebelled against Athens, triggering the Social War. Chares was given joint command of the Athenian war effort, alongside Chabrias. Their first effort was a joint land and sea attack on the rebels who had concentrated at Chios. Chares commanded the land attack, Chabrias the naval attack. The battle of Chios (357 or 356 BC) ended as an Athenian defeat in which Chabrias was killed, leaving Chares as the sole commander. He only had 60 ships and was unable to intervene as the allies attacked Lemnos and Imbros, and then besieged Samos.
In 356 the Athenians raised a new fleet. The command was either given to Iphicrates and Timotheus, or to Iphicrate's son Menestheus, with Iphicrates and Timotheus along as advisors. Chares either shared the command of the joint fleet, or brought his original fleet to the same area to make sure he would share the credit for any victory. The Athenians headed towards Byzantium, in an attempt to raise the siege of Samos. The allies were forced to rush north to defend their most important city. As the two fleets approached each other, probably at Embata, in the straits beween Chios and the mainland of Asia Minor, a storm blew up. Iphicrates and Timotheus decided to ride out the storm, but Chares refused to join them, and rushed ahead. He was defeated in the resulting battle of Embata, After the battle he complained to the people of Athens. Iphicrates and Timotheus were put on trial. Timotheus was found guilty, fined and probably went into exile. Iphicrates may or may not have been found guilty, but he wasn't given another command.
This just left Chares, who was now short of supplies and money. In order to try and raise some funds, he agreed to fight for Artabazus, satrap of Hellespontine Phrgia, who was then involved in a revolt against Artaxerxes III (Satrap's Revolt). Chares won at least one victory for Artabazus, and was richly rewarded for his success, but this merely provoked Artaxerxes. He sent an ultimatum to Athens, demanding that Chares should be recalled. This was backed up by the news that the Persians were building a large fleet. Athens was exhausted, and had to agree to the terms of a new 'King's Peace'. She lost most of the Second League, apart from a few key islands in the Cyclades and possession of the Chersonese, key to her grain supplies.
In 353 Chares was sent to the Chersonese to enforce Athenian authority at Sestus. He captured the town, killed the men and sold the women and children into slavery. While he was on his way to or from Sestus he passed close to Thessaly, just as the Phocians were campaigning against Philip II of Macedon (Third Sacred War). Athens was often allied with Phocis during this was, so his presence might not have been by chance. Whatever the original plan was, it was upset by Philip's victory at the battle of the Crocus Field. Many of the Phocians attempted to escape to the safety of the Athenian fleet, and were drowned. Amongst them many have been their commander Onomarchus, whose exact fate is reported differently in different sources.
In 349 BC Philip II of Macedon attacked the Chalcidic League, after Olynthus, the key power in the League, attempted to negotiation an alliance with Athens. Chares was given command of the first Athenian force that was sent to help Olynthus, but achieved very little before he was replaced by Charidemus, recalled to Athena and charged with misconduct. In 348 Chares was put back in command, at the head of a force of 2,000 hoplites, 300 cavalry and 17 triremes, largely made up of Athenian citizens. He has some success during this campaign, but caused some controversy when he gave a feast using some of the money taken from Delphi during the Third Sacred War. Athens had been an ally of the Phocians (who had seized the sanctuary at Delphi) for much of this war, and some of the treasure taken from the Oracle had ended up in Athens. Once again Chares was prosecuted on his return to Athens.
In 346 Chares was sent to Thrace to help King Cersobleptes, who was then at war with Philip II. When the fighting began, Chares was nowhere to be found, probably having taken his fleet off on a private raid. Cersobleptes complained, and the Athenians had to send a squadron to try and find Chares. Later in the year Chares reported that Cersobleptes's position was helpless, and this may have helped convince the Athenians to make peace with Philip (Peace of Philocrates).
For the next few years Chares may have lived at Sigeum, at the mouth of the Scamader River in the north-western corner of Asia Minor.
The peace with Philip didn't last for long. In 340 BC the Athenians agreed to support Byzantium, but they made the mistake of placing Chares in command of their forces. The Byzantines didn’t trust him, and wouldn't let him into the city. At one point he was fooled by Philip, who sent four light but well manned ships ahead of his fleet. Chares, who was waiting to ambush the main Macedonian fleet, fell for the trick and attempted to catch these four ships, but he was unable to catch them. While he was distracted Philip's main fleet sailed past to safety. Chares spent most of his brief period in the area raiding Athenian allies, before being replaced by Phocion, who was able to work so well with the Byzantines that Philip eventually had to abandon the siege.
This was a short-lived success for the Athenians. Philip was drawn south by the outbreak of the Fourth Sacred War. His presence in southern Greece forced the Athenians and Thebans to ally together, but even their combined strength wasn't enough. After a rapid advance that saw him bypass Therompylae, Philip paused in Phocis. The Athenians and their allies were able to block the mountain passes into Boeotia and Amphissa. Chares and the Theban general Proxenus were given the task of defending the passes to Amphissa. Polyaenus reports that Philip fooled them into dropping their guard by allowing them to capture a fake message to his general Antipater, informing him that due to a revolt in Thrace the expedition into southern Greece would have to be abandoned. Philip was able to cross the key passes, putting him on the Boeotian side of the mountains, and forcing the allies to retreat to Chaeronea.
Chares was one of the Athenian commanders at the battle of Chaeronea, where Philip finally defeated the southern Greek cities. Chares's role in the battle is obscure, and he doesn't appear to have been punished by either side in the aftermath.
Alexander the Great wasn't quite as forgiving. In 335 Chares was one of a list of men who he wanted Athens to hand over, although he was later persuaded to forgive all but Charidemus. In 334 Chares was living in Sigeum once again, and he paid his respect to Alexander the Great during his trip to Troy early in his invasion of the Persian Empire.
Despite this Chares's last recorded military effort was actually against Alexander. In 333 BC Pharnabazus and Autophradates, two of Darius III's commanders, captured Mytilene. Chares was put in command of the place, but he was forced to surrender it to the Macedonians in 332 BC. After that he disappeared, possibly back into retirement at Sigeum.