More recently, Menyllus, the Macedonian garrison commander, had also tried to give Phocion money, insisting he take it for the sake of his son. Phocion, it was well known, was father to a wild and free-spending youth, Phocus, who indulged in upscale drinking parties and in the posh athletic event called apobatēs.Phocus became good enough at this event, which involved jumping on and off a moving chariot clad in full armor, to win first place at an Athenian sports festival, and Phocion reluctantly went to the victory party for his son. At the door he saw that the hosts had provided footbaths of spiced wine for arriving guests. That was the last straw for Phocion. He packed Phocus off to Sparta and enrolled him in that city’s famously ascetic military training. “If my son changes his ways and learns self-restraint, then his inheritance from me will suffice,” Phocion explained to Menyllus as he turned down the proffered funds. “As he is now, nothing will be enough.”

Phocion had navigated three decades of his city’s conflict with Macedon—years that had seen the exile or execution of many politicians—without a fall from grace. The Athenians had awarded him the epithet chrēstos, “Do-good,” for his devotion to public service. The Macedonian generals, and Antipater especially, admired him as a warrior, a tough old bird like themselves who did not yield to the rigors of the march or the ills of old age. But even for this most expert of political survivors, the middle path between Athens and Macedon was becoming harder to steer. Events were about to spiral out of Phocion’s control, and the moderation that had been the glory of his career was about to be trampled by extremism and rage.

The city’s poor, though lacking a vote or a voice, had one cause in common with the propertied class, hatred of the Macedonian garrison. This armed camp posed an implied threat: the city, which relied on food imports shipped through Piraeus, could be cut off from its harbor and starved if it misbehaved. The garrison’s presence was a daily humiliation, and now that Antipater was returning to Europe, where he could be easily reached by envoys, speakers in the Assembly began agitating for its removal. This was Athens’ first attempt since the Hellenic War to loosen its yoke, and it quickly gained support.

Phocion and Demades disagreed over the garrison. Phocion was unwilling to approach Antipater and ask for its removal. He had come to regard the oligarchy as the new reality of Athenian politics, a fait accompli that should not be tampered with. Demades was more restless and ambitious, and more aware of the impetus for change. The city’s longing for autonomy and democracy was a potent force, which might bring him greater power in Athens, could he but harness it.

The Assembly voted to send an embassy about the garrison, but Phocion refused to go. Demades stepped into the breach and accepted the assignment. He took his son Demeas with him and departed for Pella, the Macedonian capital, to pay a visit to old man Antipater, just then returning from Asia. It would be the last road he would ever travel.

2.

CASSANDER AND ANTIPATER, DEMADES AND DEMEAS (PELLA, SPRING 319 B.C.)

Antipater had come home, but the Asian campaigns had wearied him. Shortly after his return he fell ill and began to fail. In his eightieth year, the oldest of the Macedonian old guard, victor in the Hellenic War, architect of the global blueprint at Triparadeisus, custodian of the joint kings, sovereign pro tempore of Alexander’s empire, was dying.

By his side was his son Cassander, one of the middle children of his many sons and daughters. Cassander had always been by his side, even during Alexander’s campaign when several of his other boys had gone east. Antipater had come to rely on Cassander as his helpmate, and Cassander was equally reliant on him. A frail boy, perhaps tubercular, Cassander did not stand on his own as much as other noblemen’s sons. It was a Macedonian custom that young men must kill a boar without aid of hunting nets before they could recline at table like an adult, but at thirty-five Cassander was still sitting upright on his couch, his hunting prowess unproved, beside his reclining father.

Since Alexander’s death, Cassander had become especially vigilant on his father’s behalf. In Asia the previous year, when he had sensed danger from Antigonus One-eye, he had gone to his father to warn him, prompting the old man to take over the joint kings. Also while in Asia he had become aware of another threat to be fended off, and an insult to be avenged, for he had there read the letter of Demades calling his father “an old and rotting rope” and proposing to Perdiccas an alliance to overthrow him.

Now Demades had arrived in Pella, and Cassander was waiting. It was clear that Demades did not know that his treachery had been uncovered, for he would not have put himself, and his son, Demeas, in Cassander’s power. Cassander had the luxury of preparing his revenge in secret. When the two Athenians appeared at the palace to discuss the garrison, they were summarily arrested as enemies of the state.

Accounts differ as to what happened next. It seems Cassander subjected Demades to a show trial, with a Greek named Deinarchus, a loyal agent of Antipater’s, serving as prosecutor. A document purporting to be a transcript of this trial has surfaced in a chance papyrus find. It shows Deinarchus producing three letters as evidence, while Demades mocks the whole proceeding, asking why the Macedonians had bothered with a trial when any tavern keeper could have stabbed him to death on his way there. This may be only historical fiction, but the manner is like that of Demades, who had become cynical in a long career serving powerful overlords. It’s easy to believe that he decried Deinarchus as a Macedonian shill, “wielding a thunderbolt borrowed from Zeus,” as the papyrus represents. Demades knew that role well. He had played it himself four years earlier when, acting as Antipater’s puppet, he got Demosthenes and Hyperides condemned to death.

The outcome of the trial was never in doubt, but Demades might have been surprised when he saw his executioner. According to Plutarch, Cassander carried out the sentence himself, and added a cruel touch perhaps of his own devising, forcing Demades to first watch the murder of his son. The spatters of the boy’s blood, in Plutarch’s lurid account, stained the folds of the father’s white cloak. Then Cassander heaped insults on Demades for betraying Antipater’s cause, and killed him.

What Antipater thought of all this is hard to say. Plutarch represents him as too ill to take part in the proceedings, perhaps even unaware of them. The larger question facing Antipater, as he neared death, was what he thought of his son generally—whether he deemed Cassander fit to take over stewardship of the kings and control of the empire.

Up to this point, Antipater had entrusted his son only with support jobs, never a command of his own. He had not given Cassander control of Europe when he himself crossed into Asia, but instead appointed Polyperchon, an undistinguished officer in his sixties, to mind the home front. Then, at Triparadeisus, he had made Cassander chiliarch, or right-hand man, to Antigonus One-eye, rather than a satrap in his own right—again entrusting power to an older man and making his son an apprentice. Perhaps he did not think Cassander was ready for leadership, or perhaps he thought that more senior men should have their turn first. He had watched as Alexander, king at age twenty, had begun chasing unheard-of visions of godhead and universal empire. That bizarre spectacle made him wary of the excesses of youth.

Whatever his reasons, Antipater, from his sickbed, made known a fateful decision: custody of the kings would pass not to his son but to Polyperchon. Cassander was to be chiliarch, once again second-in-command, to the new ruler.