Olivia: The greatest conqueror in history, Alexander the Great, might be one of history's most overrated figures. Jackson: Whoa, hold on. Overrated? The man conquered the known world before he was thirty. His name is literally the benchmark for ambition. What are you talking about? Olivia: I'm talking about his father, Philip II of Macedon. Philip was the one who built the unstoppable army, he designed the grand strategy to invade Persia, and he unified Greece for the first time in history. You could argue that Alexander just inherited the keys to a world-class war machine and drove it off a cliff of ambition. Jackson: Okay, that is a spicy take. I love it. You’re saying he was the beneficiary of some serious generational wealth, but in military form. Olivia: Exactly. And that's the complex picture we get from the book we're diving into today: Alexander the Great by Philip Freeman. What's fascinating is that Freeman is a classicist with a Ph.D. from Harvard, and he wrote this as the first major, narrative-focused biography of Alexander for a general audience in a generation. He really wanted to tell a compelling story, not just a dry history. Jackson: A compelling story, huh? Well, that hook you just threw out is a pretty compelling start. So, let's get into it. Was Alexander just riding his dad's coattails? Was he just a lucky kid who inherited the family business of world domination?

Olivia: That’s the perfect question to start with, because to understand Alexander, you absolutely have to understand his father, Philip. Before Philip, Macedonia was this backwater kingdom, a place the sophisticated Greeks in Athens looked down on as being full of barbarians. The Macedonian army was basically a part-time militia. Jackson: So what was the secret sauce? What did Philip do that changed everything? Olivia: It started when he was a young man. Philip was sent as a political hostage to the Greek city of Thebes, which at the time was the dominant military power. He wasn't locked in a dungeon; he was a guest in the house of a top general. For three years, he got a front-row seat to the most advanced military thinking of the day. He studied their tactics, their training, their discipline. He was essentially a foreign exchange student at an Ivy League school for warfare. Jackson: Wow. So he was learning from his enemies, or at least his rivals. What was the biggest thing he took away from that experience? Olivia: He learned that a professional, full-time army could beat any citizen-militia. When he returned to Macedonia and became king, he put that knowledge to work. He created a professional army and equipped them with a revolutionary new weapon: the sarissa. Jackson: The sarissa. What exactly is that and why was it such a game-changer? Olivia: Imagine a spear, but super-sized. The standard Greek spear was about six to nine feet long. The sarissa was eighteen feet long. It was so long it had to be held with two hands. When the Macedonian phalanx—their main infantry formation—lowered their sarissas, they presented this impenetrable wall of spear points. The enemy, with their shorter spears, couldn't even get close enough to fight. Jackson: That’s an incredible advantage. It’s like bringing a sword to a knife fight. You can strike from a distance your opponent can't match. Olivia: Precisely. And Philip drilled his army relentlessly. They became a disciplined, professional fighting force unlike anything the world had seen. He also perfected the use of cavalry and siege engines. By the time Alexander came of age, he wasn't inheriting a group of farmers; he was inheriting the most sophisticated and deadly military machine on the planet. Jackson: Okay, so the hardware was top-notch. But what about the software? What about Alexander himself? Was he just a figurehead, or did he have something special? Olivia: Oh, he was definitely special. Freeman tells the famous story of Bucephalas, this magnificent but wild horse that no one could tame. Philip was about to send the horse away, but a young Alexander, maybe twelve or thirteen, spoke up. He said he could ride it. Jackson: I can imagine his father rolling his eyes. "Sure you can, son." Olivia: Pretty much. But Alexander had noticed something no one else had: the horse was afraid of its own shadow. So he calmly turned the horse to face the sun, so its shadow was behind it. He spoke to it gently, stroked it, and then swung himself onto its back and rode it easily. Jackson: That’s incredible. It shows this amazing insight, this ability to see what others miss. Olivia: Exactly. And Philip saw it too. Freeman includes that legendary quote from Philip, who wept with joy and told his son, "My son, you must seek out a kingdom equal to yourself—Macedonia is not big enough for you!" So Philip knew he had a prodigy on his hands. But the family dynamic was incredibly volatile. Jackson: Right, you mentioned his mother, Olympias. The book paints her as this... intense, almost mystical figure. What was her role in all this? Olivia: Olympias was a princess from a neighboring kingdom, and she was fiercely ambitious for her son. She was a devotee of strange, ecstatic religious cults and was rumored to sleep with snakes. She instilled in Alexander this belief that he was special, that he was destined for greatness, maybe even descended from a god. The relationship between Philip and Olympias was toxic. They fought constantly. Jackson: So you have this military genius father and this fiercely ambitious, mystical mother. That’s a potent cocktail for a kid's upbringing. Olivia: It really is. And the tension was always there. Freeman recounts a scene at a wedding banquet after Philip divorced Olympias and married a younger woman. The bride's uncle gave a toast, praying for a "legitimate" heir. Alexander, insulted, threw his wine cup at him. Philip, drunk, drew his sword and lunged at his own son, but stumbled and fell. Alexander just looked at him and said, "Look, everyone! The man who wants to cross from Europe to Asia can’t even make it from one couch to the next." Jackson: Ouch. That is a brutal thing to say to your father, the king. It shows you just how broken that relationship was. The whole foundation of his rise seems built on this brilliant but deeply dysfunctional family.

Olivia: And that ambition, fueled by both his parents, wasn't just about winning battles. It was about crafting an image. This is where Alexander's own genius really shines through—as a master of propaganda and political theater. Jackson: Propaganda? Like, ancient political ads? How did that work back then, without social media or TV? Olivia: It was all about symbolism and storytelling. One of the first things he did after crossing into Asia was make a pilgrimage to the ruins of Troy. He was obsessed with Homer's Iliad and saw himself as the new Achilles, the greatest warrior of all time. He made sacrifices at Achilles's tomb, ran naked around it with his companions, and dedicated his armor at the temple of Athena. Jackson: So he's literally casting himself in the role of a mythical hero. He's telling his army, and the world, "This isn't just a war, it's an epic saga, and I am the star." Olivia: Exactly. He's creating a narrative. But his most brilliant move came in Egypt. After conquering it, he made a long, dangerous journey deep into the desert to visit the Oracle of Zeus-Ammon at the Siwa oasis. This oracle was hugely respected throughout the Greek world. Jackson: Why go to all that trouble? What was he hoping to get? Olivia: He wanted a divine endorsement. According to the story, when Alexander approached the high priest, the priest, who may not have spoken Greek very well, greeted him with "O paidon," which means "O, my son." But Alexander chose to hear it as "O pai Dios," which means "O, son of Zeus." Jackson: Wait, so a potential linguistic slip-up becomes a divine proclamation? That is brilliant political theater! He's not just conquering, he's building a personal brand as a demigod. Olivia: He absolutely is. He immediately started putting the ram's horns of the god Ammon on his coins. From that point on, he wasn't just Alexander, King of Macedonia. He was Alexander, son of a god. It was a way to legitimize his rule over this vast, diverse empire he was building. A mortal king can be questioned. A god's son? Not so much. Jackson: That makes so much sense. What about his famous 'mercy,' like with Darius's family after the Battle of Issus? The Persian king’s mother, wife, and children were captured. Was that just part of the act too? Olivia: Freeman argues it was a masterful blend of genuine decency and calculated strategy. After the battle, Darius's mother, Sisyngambris, mistakenly bowed to Alexander's taller friend, Hephaestion, thinking he was the king. It was a huge breach of protocol. Jackson: Oh, that's an awkward moment. How did Alexander handle it? Olivia: He just laughed it off and said something incredible. He told her, "Don't worry, Mother. He too is Alexander." He was referencing the idea from his tutor, Aristotle, that a true friend is another self. He treated the royal women with the utmost respect, promised to provide dowries for the daughters, and essentially adopted them. Jackson: So he's positioning himself not as a brutal conqueror, but as the new, benevolent head of the Persian royal family. Olivia: Precisely. It sent a powerful message to the Persian aristocracy: "Surrender to me, and you will be treated with honor. I am not here to destroy your world, but to lead it." It was an incredibly effective way to win over the hearts and minds of the people he had just conquered. He was a performer, and the world was his stage.

Olivia: But this performance of a benevolent, god-like ruler starts to crack the further he pushes east. The pressure of the campaign, the vast distances from home, and the intoxication of absolute power begin to corrupt him. And Freeman's book doesn't shy away from this dark turn at all. Jackson: This is the part I'm really curious about. The hero's journey always has a dark side. Give me the most chilling example of his paranoia from the book. Olivia: It has to be the case of Philotas and his father, Parmenion. Parmenion was Philip's most trusted general, a man who had been with the Macedonian kings for decades. He was a legend. His son, Philotas, commanded Alexander's elite cavalry. They were one of the most powerful families in the army. Jackson: So, pillars of the establishment. What happened? Olivia: A low-level plot to assassinate Alexander was uncovered. The plotters were insignificant, but Philotas had heard about it and failed to report it to Alexander immediately. He claimed he didn't think it was credible. But Alexander's other generals, who were rivals of Philotas, saw an opportunity. They convinced Alexander that Philotas's silence was proof of his involvement. Jackson: That sounds like a classic court conspiracy. A flimsy pretext to take out a rival. Olivia: It was. Alexander had Philotas arrested, tortured, and forced into a confession. Then, following Macedonian custom, he was put on trial before the army and stoned to death. But Alexander knew that as long as the father, Parmenion, was alive, he would be a threat seeking revenge. Jackson: So what did he do? Olivia: He sent assassins on racing camels across the desert to Ecbatana, where Parmenion was guarding the army's treasury. They carried a forged letter, supposedly from his dead son. As Parmenion was reading the letter, the assassins stabbed him to death. He killed his most loyal, most experienced general without a trial, without any proof, based purely on paranoia. Jackson: That's terrifying. It's like something out of The Godfather. It shows a complete shift from the confident leader to a paranoid tyrant who sees enemies everywhere. What about his famous temper? The book mentions the murder of Cleitus. Olivia: That story is even more personal and tragic. Cleitus was another one of his senior officers, a close friend, and the man who had personally saved Alexander's life at the Battle of the Granicus by cutting off the arm of a Persian nobleman about to kill him. Jackson: So this man literally saved his life. They must have been incredibly close. Olivia: They were. But years later, at a banquet in Samarkand, everyone was drunk. Alexander was boasting and encouraging his flatterers, who were saying his achievements far surpassed his father Philip's. Cleitus, an old-guard Macedonian loyal to Philip's memory, got angry. He stood up and started criticizing Alexander for adopting Persian customs and disowning his own father. Jackson: Oh, that's a dangerous thing to do to a man who thinks he's the son of a god. Olivia: It was a fatal mistake. The argument escalated. Cleitus quoted a line from a Greek play: "Alas, what evil customs reign in Greece!" Alexander, enraged, grabbed a spear from a bodyguard and ran Cleitus through, killing him instantly. Jackson: Wow. He killed the man who saved his life, in a drunken rage. What happened after? Did he feel any remorse? Olivia: The book says he was immediately consumed by guilt. He pulled the spear from Cleitus's body and tried to turn it on himself, but his bodyguards stopped him. He locked himself in his tent for three days, refusing to eat or drink, just weeping. It was a moment where the monster and the man collided. It showed the deep rift that had grown between him and his Macedonian veterans, who saw him becoming more of a Persian despot than a Macedonian king.

Jackson: So, after all this... the military genius inherited from his father, the brilliant propaganda, and then the descent into paranoia and brutality... what's the final picture of Alexander we're left with? Is he a hero or a villain? Olivia: Freeman's book suggests he's neither, and that's really the point. He was a product of a brutal, violent world. He was a man of immense, almost supernatural talent and ambition who achieved unparalleled success, but was ultimately consumed and corrupted by the very power he fought so hard to win. Jackson: So it's a cautionary tale, in a way. The book isn't trying to give us a simple verdict. Olivia: Exactly. It leaves us with this profound warning about the nature of unchecked ambition. Alexander wanted to conquer the world, and he did. But in the process, he lost a part of his own humanity. He became isolated, paranoid, and tyrannical. The book shows that the line between a great leader and a great monster can be terrifyingly thin. Jackson: It makes you think about how we remember historical figures. We love the simple stories of heroes and villains, but the truth is always so much messier, so much more complicated. It's a powerful reminder to look past the legend and see the flawed human being underneath. Olivia: It really is. And for anyone listening who wants to explore that messy, brilliant, and terrifying story for themselves, we can't recommend Philip Freeman's Alexander the Great enough. We'd love to hear your thoughts. Do you see him as a visionary leader or a paranoid tyrant? Let us know on our social channels. Jackson: This is Aibrary, signing off.