After his victory at Gaugamela, Alexander the Great’s worst tendencies – his vanity above all, came out in greater force. When he effectively ended Persian resistance to his conquest, he began his policy of blending Greek and Asiatic culture. He recruited Persian soldiers and often encouraged his men and officers to marry Persian women. The policy caused discontent within Alexander’s ranks, especially among the old guard of officers who served under his father, Philip II. This discontent led to the first substantial plot to kill Alexander and the trial of Philotas. What can one learn from this episode? Let’s take a look.
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And now back to the show.
Who Was Philotas?
Philotas was the commander of Alexander’s crack Companion Cavalry and son of the general Parmenio. Parmenio had been the longtime second-in-command for both Alexander and Philip and had recently been made governor of Media, with his seat at Ecbatana, a crucial crossroads in the region. The Persian royal treasury of 180,000 talents was among his assets. An Attic talent was about 57 pounds of pure silver, so this sum would be about $2.8 billion in today’s money. As a result, father and son had an immense power base.
Having power enough to threaten a proud king is a troublesome problem on its own, but the problem was worse with Alexander. Deep down, he was an insecure man, and his insecurities grew after Gaugamela. He constantly felt the need to defend his ego and assuage his vanity. He killed his friend Cleitus the Black in a drunken rage. This was a man who needed to feel secure and not threatened in either his safety or his reputation.
The conspiracy Philotas found himself dragged into ran afoul of that part of Alexander’s psyche.
After Alexander and his men killed the usurper Bessus and avenged the murder of Darius III, his soldiers became more and more discontent. Campaigning in Afghanistan will do that to a man.
With Darius dead and avenged, and the Persian capitals in Macedonian hands, the troops wanted to go home. Their mission had been accomplished. They had not signed up to follow Alexander to the end of the world. However, he continued on. Alexander the Great was never one to let criticism get to him.
Unsurprisingly, some officers in these badlands conspired against his life. In late 330 BC, a man named Dimnus gathered some peers and planned to kill the King. However, like most conspiracies, leaks came out immediately.
According to Diodorus Siculus, Dimnus blabbed his plans to his lover, a young boy named Nicomachus. The latter’s brother, Cebalinus, took action on the confused boy’s behalf. Diodorus (whose account is quoted here) and Plutarch both mention the following incident:
 He went to the court, met Philotas and talked with him, and urged him to tell the whole story to the king as quickly as he could. It may be that Philotas was actually a party to the plot; he may merely have been slow to act. At all events, he heard Cebalinus with indifference, and although he visited Alexander and took part in a long conversation on a variety of subjects, said no word about what had just been told him.
 When he returned to Cebalinus, he said that he had not found a suitable occasion to mention it, but would surely see the king alone the next day and tell him everything. Philotas did the same thing on the next day also, and Cebalinus, to insure himself against someone else betraying the plot and putting him in danger, dropped Philotas and accosted one of the royal pages, telling him all that had happened and begging him to report it to the king immediately.
 The page brought Cebalinus into the armoury and hid him there, went on in to the king as he was bathing and told him the story, adding that he had Cebalinus concealed in the vicinity. The king’s reaction was sharp. He arrested Dimnus at once and learned everything from him; then he sent for Cebalinus and Philotas.
 The whole story was investigated and the fact established. Dimnus stabbed himself on the spot, but Philotas, while acknowledging his carelessness, nevertheless denied that he had had any part in the plot and agreed to leave judgement concerning him to the Macedonians.
This was Philotas’ mistake. It appears that he believed the plot was just a bunch of nonsensical rumors, but by not being forthright with the King, by assuming he could judge the veracity of the rumor in Alexander’s place, he put himself in a terrible position.
It didn’t help that Alexander knew of Philotas’ boasting to one of his lovers, a girl named Antigone. Plutarch says that while in bed with her, he often bragged that all of the success in the campaign was due to him and his father, not the King.
Insulting anyone’s pride is not a good method of persuasion. Insulting the pride of a powerful, absolutist megalomaniac like Alexander the Great is downright dangerous.
The Trial of Philotas
Diodorus says little about the actual court proceedings. He only mentions that Philotas was condemned, tortured, and executed. With Philotas dead, there was no way that Alexander could allow Parmenio to live. He was simply too powerful an enemy. The King sent a rapid response hit squad and assassinated the general before the news of his son’s death could reach him.
Alexander isolated the men who were loyal to Parmenio and Philotas. Diodorus says:
Alexander selected from among the Macedonians those who made remarks hostile to him and those who were distressed at the death of Parmenion, as well as those who wrote in letters sent home to Macedonia to their relatives anything contrary to the king’s interests. These he assembled into one unit which he called the Disciplinary Company, so that the rest of the Macedonians might not be corrupted by their improper remarks and criticism.
The containment worked, but the discontent would grow in the coming years, as it became increasingly clear that Alexander intended to go far further than his troops first thought. It was an ancient example of a modern term: “mission creep.”
Either way, the trial of Philotas and assassination of Parmenio were the end of the old guard who had fought under Philip. The new generation were now fully in control and eager to expand their influence in the wake of the old guard’s downfall.
Power comes with enemies. Philotas had his fair share. When word got out that he had dismissed the conspiracy, competitors saw their chance to get rid of him and enrich themselves by encouraging Alexander’s vices, which they appear to have known better.
You must always know who you’re dealing with, especially when you’re in a position of responsibility to someone more powerful than you. Beneath you, others will covet your position. Above you, the leader might have his suspicions.
Philotas had campaigned with Alexander the Great long enough to know his personality. He should have known his temper and encouraged his vanity in appropriate ways, making him feel secure. He did the opposite one times too many and suffered for it.
One of the biggest difficulties in life is escaping your own narcissism. If you have power, it can cost you everything. Always try to escape from it.
Read more about this in Lives of the Luminaries, in particular the chapter on the escape of Charles II, who successfully combated his narcissism and lived as a result.