Some people think the world revolves around them. If you’re Alexander the Great, you’d be right. History’s most successful general, Alexander reshaped half the world in his image. What kind of man does it take to do that? One of the most charismatic, brilliant, and obsessed men of all time.
1. His Dad Was Scary
Alexander the Great’s father was King Philip of Macedon, a fierce warrior who looked every bit the part with his missing eye and wicked scar. His mother was Queen Olympias, one of many women married to Philip—but of those women, Olympias was definitely the most terrifying.
2. His Mom Was Scarier
How scary was Olympias? According to history, once, when she defeated a rival queen, she sent the woman a rope, a cup of poison, and a sword, along with a simple message: You may choose the tool with which you end yourself. The woman, it should be noted, took the rope.
That’s the kind of woman who was raising Alexander. It wasn’t long before people noticed her boy was special.
3. He Showed Promise
When Alexander was just a boy, he saw his father’s men trying—and failing—to mount a massive horse. The boy asked if he could give it a try, and after several attempts, he succeeded. His father, beaming, cried out, “My boy, you must find a kingdom big enough for your ambitions. Macedon is too small for you". He was right about that.
None of them yet realized that the horse, Bucephalus, would carry Alexander across half the world.
4. His Parents Were Worried
Alexander grew into a talented, intelligent, outgoing, and charismatic young man—but there was one thing about him that made his parents nervous. If he was going to be king one day, he was going to need lots of queens to make lots of babies.
In this regard, Philip and Olympias had their doubts…
5. They Paid For A Lay
If Alexander was going to be a King, then his parents wanted to make him a Man first. According to Greek historian Athenaeus, Philip and Olympias brought in an expensive courtesan from Thessaly to…put some hair on Alexander’s chest.
6. He Refused The Offer
Alexander the Great was not like other men—in a lot of ways. For instance, when his parents brought a concubine to make a man out of him, he refused the offer. Many historians came to a simple conclusion: Alexander the Great had a lot of interests, and flesh was not one of them.
Some other historians, however, had another idea…
7. He Loved His Bros
Maybe it wasn’t that Alexander wasn’t interested in the flesh…maybe his parents just brought him the wrong kind of flesh. From his youth through his campaigns, Alexander the Great was accompanied by a group friends called the “Companions”. These men grew up with Alexander, trained with Alexander, and ended up ruling half the world after he was gone.
Alexander was incredibly close with all of these men, but one of them meant more to him than all the rest.
8. He Was A Powerful Friend
The Companions, who all met Alexander when they were young, had no idea where he’d take them. Ptolemy ended up Pharaoh of Egypt. Cassander became king of their Macedonian homeland. But of all the Companions, Alexander was by far the closest with one man: Hephaestion.
But while some of the companions became kings, Hephaestion had a much darker fate awaiting him.
9. He Learned From The Best
King Philip wanted to make sure his son got the best education possible, so why not hire one of the greatest geniuses in history? Philip sent Alexander and his friends to study under Aristotle, who taught them philosophy, medicine, religion, logic, statecraft, and more.
Everything you might need to know if you planned to rule the world.
10. They Were REALLY Close
Aristotle couldn’t help but comment on Alexander’s relationship with Hephaestion, saying they were like one soul living in two bodies. The exact nature of the relationship between the two young men remains unclear to this day, but one thing is very clear: Alexander the Great cared about Hephaestion more than anyone else.
Unfortunately, that would turn out to be his Achilles heel.
11. His Tutor Had No Choice
Aristotle had the privilege of training a future god-king—but he only did it at the point of a sword. Throughout Alexander’s childhood, King Philip was busy conquering one Greek city after another, and he had already razed Aristotle’s hometown and sold its citizens into slavery.
Philip only got Aristotle to become Alexander’s tutor by agreeing to rebuild the city and to free its citizens. How's that for a signing bonus?
12. He Loved Poetry
Aristotle taught Alexander a lot, but nothing clicked with him more than epic poetry. Alexander became obsessed with the Iliad and later carried a copy with him wherever he went. He saw himself in the legendary Achilles. In that regard, he wasn’t far off.
13. He Was A Total Hunk
Alexander the Great was stocky, blonde, and according to many sources, unbearably handsome, with blonde curls falling to his shoulders. If he thought he was a god, he certainly looked the part. But Philip was right: Macedon was too small for him.
Luckily for Alexander, the entire world was right around the corner.
14. There Was An Enemy Next Door
People today think of Greece as the West and Iran as the East—but in Alexander’s day, they weren’t so far apart. The Persian Empire of modern-day Iran stretched all the way to the Aegean Sea, bumping right up against Alexander’s world.
Everyone in Greece remembered Thermopylae, the 300 Spartans, and the Persian invasion of their homeland. For Alexander, even more so—because there were Persians right in his backyard.
15. He Rubbed Shoulders With The Enemy
Greeks and Persians weren’t so different, and several Persian nobles actually lived in exile in King Philip’s court. One of them was a general named Artabazos, and he brought along his daughter, the beautiful Barsine. These Persians exposed Alexander to their culture—but that’s not all they exposed him to.
16. He Had A Fling
Even as he grew into a young man, Alexander still shunned the pleasures of the flesh—mostly. Later in his life, Alexander would run into Barsine once more, and if ancient historians are to be believed, sparks flew.
Maybe they connected over their memories of the Macedonian court, but Barsine allegedly gave birth to Alexander’s illegitimate son, Heracles of Macedon, not long after.
17. He Was Liquidating Before He Could Vote
When Alexander hit 16, his education ended, and it was time to take up the sword. Macedon was growing incredibly powerful, but there were always other Greek city-states trying to revolt, invade, or generally make a nuisance of themselves.
Before voting age, Alexander had already fought and won several pitched battles, even once saving his father’s life. It was the best training possible for what lay ahead.
18. He Helped Conquer Greece
Alexander was there for some of the most legendary moments in Greek history—even when he wasn’t involved in the story. He rode alongside his father south into Greece, where Philip sent a message to the Spartans: If I invade your lands, I'll wipe you out.
The Spartans gave a legendary one-word reply: "If". The story makes the Spartans look tough and terrifying—but not a lot of people know what happened next.
19. They Made The Spartans Look Like Fools
The Spartans talked a big game—but they had nothing on Philip and Alexander. Father and son waltzed their army into Sparta and carved it up for themselves, leaving the “legendary” Spartans with nothing. I wonder if they had any clever one-word responses to that.
20. His Dad Found A New Woman
It seemed like Alexander had it made. He was the chief nepo-baby of the most powerful man in Greece—but when you’re playing the game of thrones, nothing is certain. In 338 BC, Philip fell in love with a new woman, Cleopatra Eurydice, and married her.
For both Alexander and his mother, that sent alarm bells ringing.
21. He Worried He Wasn’t Enough
Queen Olympias was from Molossia, which meant Alexander was only a half-blooded Macedonian. If Philip had a son with Cleo, that boy would be full Macedonian. Power-hungry as they were, this did not sit well with mother and son—then, at Philip’s wedding, it seemed their worst fears were coming true.
22. They Voiced His Fears Aloud
Cleopatra’s uncle Attalus was an important Macedonian soldier, and on the night of his niece’s wedding, he had a little too much to drink. Deep in his cups, Attalus loudly prayed that Cleopatra might give Philip a son, so a full Macedonian could take over the throne.
How do you think Alexander and his mom felt about that?
23. His Father Nearly Ended Him
Alexander stood up and threw his own cup at Attalus’s head. It was almost the last thing he ever did. His own father Philip stood by Attalus, and drew his sword to run his own son through. But remember how Attalus had been drinking? Well, Philip was right there with him, and he slipped and fell before landing the fatal strike.
But one thing was clear: All was not well in Macedonia.
24. He Ran For His Life
Macedonian diplomacy involved a lot more “stabbing” than modern cultures, and Alexander knew when he was in danger. He and Olympias fled north and he ended up in Illyria, where he took refuge with a local king and planned his next move.
But back in Macedonia, things were only getting worse.
25. He Thought He Was Finished
Alexander still got the news in exile, and that’s how he heard that one of his half-brothers, Philip, was going to get married to a Persian princess. This sent a chill down his spine: Was this an indication that King Philip meant to make Alexander’s brother his heir?
Alexander hatched a new plot to fortify his position—but he didn’t really understand what was happening.
26. He Didn’t Have To Be Worried
Philip wasn’t stupid. Alexander was a obviously special kid—remember Bucephalus? There was no way Philip was making anyone else his heir. All of Alexander’s paranoia and scheming were pointless. When Philip heard about his son’s latest plot, he had his men track down Alexander and bring him home in chains, mostly to tell him to stop being an idiot.
Just in time, too—because Philip’s number was up.
27. His Dad Met A Brutal End
King Philip was a fearsome general who, for the first time in history, brought all of Greece under one command. Then one day in 336 BC, while attending a wedding, one of his own bodyguards, Pausanias, spiked him in the back.
Just like that, everything Philip had worked for fell to Alexander. It was a lot of responsibility—but Alexander hit the ground running.
28. He Didn’t Waste Any Time
The cutthroat world of Macedonian politics taught Alexander well: Before Philip’s body was even cold, he set about eliminating any potential rivals to his throne. He immediately had a cousin and several other Macedonian princes eliminated.
Though ruthless, he could at least justify this slaughter. What his mother did, however, was just downright sadistic.
29. His Mom Went Too Far
Remember Cleopatra Eurydice, Philip’s pure-blooded Macedonian wife? Olympias never forgot about her. When Alexander took over, Olympias had both Cleopatra and her daughter by Philip burned alive.
This was too far even for Alexander, and he was furious when he found out. But he didn’t have time to scold his mother—half of Greece was in revolt, and Alexander had his work cut out for him.
30. He Had To Prove Himself
Alexander was a new king in a precarious position. His advisors recommended he use diplomacy to settle the rebellious city-states down south. That wasn’t Alexander’s style. Instead, he gathered 3,000 of his finest Macedonian cavalry and headed south to deal with the Greeks personally.
31. He Met A Cynic
On his march through Greece, Alexander only met a single person who could stand up to him: The deranged philosopher, Diogenes. Everyone in Greece knew who Alexander was by that point, but when Diogenes saw him, unlike everyone else in the world, he wasn’t impressed.
32. He Was Impressed
Diogenes looked more like a hobo than a legendary philosopher, but Alexander couldn’t help but take notice. He asked the man if there was anything he could do for him. Diogenes gave a simple answer: "Move, you’re blocking my sunlight".
Delighted, Alexander allegedly cried, “If I weren’t Alexander, I’d like to be Diogenes”.
33. He Unified Greece
It didn’t take long for the Greek city-states to realize that Alexander was every bit the man his father was. In case they weren’t sure, he razed the city of Thebes when they revolted, and that proved it. By 334 BC, Alexander had an army of Greeks behind him, and he started preparing to do what his father had dreamed of.
The Greeks were going to conquer the world.
34. He Entered Asia
When Alexander the Great crossed the Hellespont into Asia, he took 8,100 infantry, 6,100 cavalry, and a fleet of 120 ships carrying another 38,000 men with him. But while this seems like a sizable force, they were going up against a leviathan. The Persian Empire stretched for thousands of miles and contained literally millions of people.
But Alexander had a secret weapon: Himself.
35. All He Did Was Win
Alexander the Great was maybe the greatest army mind in history. He first met the Persians on the field in Northern Turkey at the Battle of the Granicus—and he wiped the floor with them. He continued on his warpath, conquering the cities along the western coast of Turkey, before turning inland, where far more legendary exploits awaited him.
36. He Cheated
When Alexander made it to the ancient city of Gordium, he heard about a local legend. The city contained the fabled Gordian Knot, which could only be undone by the future King of Asia. Alexander liked the sound of that…so he just drew his sword and hacked the knot to pieces.
Anyone who thinks that’s cheating obviously doesn’t know what happened next.
37. He Pushed Himself Too Hard
Alexander was a young man fresh on the campaign, but he always pushed himself too hard. Before even reaching Syria, his hard-fighting/hard-partying ways (the Macedonians loved their grape beverage after a long day) left him trapped in a sickbed, unable to press on. He'd barely started, and already he needed a long pause to recover his strength. But it was going to take more than that to stop Alexander the Great.
What lay behind him was only the tip of the iceberg. Alexander wanted to conquer the entire Persian empire—and that meant defeating the King of Kings Darius III, who lay just ahead.
38. He Had To Face The King Of Kings
Darius was by far Alexander’s greatest challenge yet. Darius had the entire might of the Persian Empire behind him, and the force he brought to face the Macedonians at Issus far outnumbered Alexander’s. But if you believe that history is shaped by great men, then the outcome of this battle was predetermined.
Alexander was great. Darius was not.
39. He Made His Rival Turn And Run
Despite his numerical advantage, Darius blinked first at the Battle of Issus. As soon as he thought the fight was turning against him, the Persian king turned tail and ran, leaving his wife, daughters, mother, and treasure behind.
Just like that, Alexander was the King of Persia. He set out what he'd accomplished to do. But this wasn’t the end of his journey. He had barely just gotten started.
40. He Became A Pharaoh
Darius was still alive, but Alexander could deal with him later. After Issus, he went on the warpath. He conquered Syria and most of the Levant, razing cities, slaughtering men, and selling women and children into slavery. Next, he continued on into Egypt, where he took the mantle of Pharaoh and founded the city of Alexandria on the Mediterranean coast.
Alexander was only 25, and he had already accomplished more than maybe any general in history. But he still wanted more.
41. He Kept Winning
After Egypt, Alexander headed for the heartland of the Persian Empire. On his way to Babylon, Darius met him on the field again at the Battle of Gaugamela. Once again, Alexander defeated the Persians and Darius fled, leaving him free to conquer the great Persian cities like Babylon, Susa, and Persepolis.
But as long as Darius was still breathing, Alexander couldn’t rest easy. Well, about that "still breathing" part...
42. He Had A New Foe To Chase
Alexander wanted to defeat Darius personally, but he never got the chance. After Gaugamela, Darius joined his relative, Bessus—who promptly ran Darius through, named himself King of Persia, and fled north into modern-day Afghanistan with Alexander hot on his heels.
The chase was on...again.
43. He Buried Darius
Before chasing Bessus north into Bactria (modern-day Afghanistan), Alexander gave Darius a funeral. And wouldn’t you know it, Alexander claimed that with his last breath, Darius had named him the successor to the Persian throne. Now, he just needed Bessus’s head…
44. He Fought An Afghan Conflict
The United States, Russia, and the British Empire all endured long, ineffective, and ultimately fruitless campaigns in the mountains of Afghanistan—and all of them followed in Alexander’s footsteps.
The Macedonian army chased Bessus through half of Central Asia, losing thousands of men in the process—yet Alexander never actually caught his prey. A betrayal from within did that job for him.
45. His Enemies Kept Turning On Each Other
Who knows how long Bessus could have evaded Alexander in Afghanistan, but his flight ended when one of his allies, a Sogdian noble named Spitamenes, betrayed him. He gave Bessus to Alexander’s general, Ptolemy, who quickly executed him.
If Spitamenes had known what was good for him, he would have stopped there. He did not know what was good for him.
46. They Finally Gave Up
Like Darius and Bessus before him, Spitamenes thought he was maybe the man to finally best Alexander. He was not. After Alexander defeated him at the Battle of Gabai, Spitamenes’s own men executed him and then sued for peace. Finally, someone did something smart for a change!
47. He Took A Pause
After Spitamenes’s defeat, Alexander, for once in his life, took a breather. He and his Macedonian generals attended a celebration at the Sogdian Rock, a fortress in the mountains of Tajikistan. At that feast, Alexander did something that was very unlike him: He fell in love.
48. He Married A Great Beauty
Her name was Roxana, the daughter of a Sogdian noble, and Alexander allegedly fell in love with her at first sight. He married her without delay—but this was a dangerous move. The Macedonians had been away from home for a long time, and Alexander was starting to act a little too...Persian for their liking.
Taking a foreigner for a wife instead of a good Macedonian woman definitely didn’t assuage their doubts. But while Alexander was smitten with Roxana, it’s not like she was the only woman for him.
49. There Was Lots Of Him To Go Around
Alexander actually married three times—all to Persian women—but this wasn't because he had too much love to go around. Each marriage was political, ensuring loyalty from his newly-conquered Persian subjects. But this plan backfired horribly. While making Persian connections, Alexander was sowing resentment among his Macedonian men.
It was only a matter of time before he pushed them too far.
50. His Relationships Were Confusing
Who did Alexander the Great really love? Was it Hephaestion, his loyal companion since childhood? Roxana, the beautiful Sogdian princess? One of his other wives? What about Barsine, who allegedly fathered his child? Most textbooks will tell you about each of these partners...but what about about Bagoas, the beautiful eunuch?
51. He Kept A Beautiful Eunuch With Him
Bagoas, a favorite of Darius, was a eunuch “in the very flower of boyhood”. After Darius fell, Alexander inherited the beautiful Bagoas, and ancient sources claim they had an intimate relationship, much as Bagoas had had with Darius before him.
Bagoas only makes the question of Alexander’s romantic life even more confused—but to be fair, love wasn’t his biggest priority. Alexander had plenty else to keep him busy.
52. He Had To Keep Moving
It seemed like any time Alexander stood still, one person or another was plotting against him. Well, good thing there’s a solution to that: Keep moving! After executing some of his men who conspired against him, Alexander turned east once more, this time with India in his sights.
But little did he realize, India was where Alexander the Great would finally meet his match.
53. He Fought Against Elephants
It had been nearly a decade since Alexander left Macedon behind him, but he still insisted his men push further. In the Far East, they razed yet more cities, faced strange foreign armies who fought with elephants, and still, Alexander’s undefeated streak continued.
But this life of constant marching, fighting, and paranoia was starting to take its toll.
54. He Was Losing His Edge
Alexander drank heavily at night, and it started to affect him. In one infamous altercation, a drunken Alexander slew Cleitus the Black, a man who had personally saved his life, for criticizing him. But Cleitus was just saying what everyone was thinking.
The men were exhausted from years of campaigning, and they barely recognized their king, who kept adopting more and more Persian customs. They had followed him quite literally to the ends of the Earth—but Alexander finally found their limit.
55. His Men Said No More
When Alexander reached the Ganges River, he finally found his men’s limit. The river was wide, deep, and thousands of enemy warriors, horses, and elephants waited for them on the other side. When Alexander told his forces to press on, they simply said, "No".
56. His Men Begged To Stop
Alexander the Great was one of the most charismatic leaders in history, but nothing he said to his men could convince them to cross the Ganges. One of his generals begged him to reconsider: None of their men had seen their families, their homes, for years. Hadn’t Alexander conquered enough?
57. They Had One Final Trial Ahead Of Them
Not even Alexander could convince his men to march any further, and for the first time in his life, he had to admit defeat. But that didn't mean their trials were over. Alexander and his men turned West to Susa, but a scorching desert lay between them and their destination.
Thousands more men lost their lives in the desert before the Macedonians finally made it back to the Persian heartland—and they weren't even home yet.
58. He Lost His Beloved
As Alexander plotted his next move, tragedy struck. His beloved Hephaestion fell ill and quickly perished. If there was any doubt as to who Alexander’s true love was, they ended here: Alexander, mad with grief, threw himself on Hephaestion’s body and lay there in tears for an entire day.
The Companions eventually had to drag him away by force, but the truth was obvious: Alexander didn’t want to live in a world without Hephaestion. Lucky for him, he wouldn’t have to for long.
59. He Threw A Feast
After giving his friend a lavish funeral in Babylon, Alexander once again set his sights on conquest. He made plans to venture into the Arabian peninsula and add to his already colossal empire. To celebrate the impending invasion, he threw a fabulous banquet. It was the last one he’d ever throw.
60. He Fell Ill
Despite everything we know about Alexander the Great, the exact circumstances of his end remain unclear. Some sources claim he came down with a fever, others called it a fit of weakness and agony. There’s one thing they agreed on: Alexander went out drinking in Babylon, he fell ill, and in June of 323 BC, he gave his last breath.
In just 32 years, Alexander the Great had remade half of the known world in his image—and he wasn’t even finished yet.
61. His Last Words Caused Chaos
Even in demise, Alexander the Great wasn’t finished reshaping the world. As he lay on his deathbed, someone asked him who his empire should go to. He responded with three simple words, the last he’d ever utter: To the strongest.
Those three words set off the Wars of the Diadochi, decades of vicious fighting between Alexander’s companions over his unwieldy empire, which collapsed almost the moment of Alexander’s passing.
62. His Wife Learned From His Mom
Alexander left no heir, but his wife Roxana was pregnant at the time. She hoped that her boy might be able to one day take up his father’s mantle (good luck), and she was willing to do anything to make sure it happened. Soon after Alexander’s demise, Roxana had both of Alexander’s other wives liquidated so they couldn’t get in her way.
She learned from Alexander well. Unfortunately, eliminating your political rivals is a double-edged sword. Cassander, one of Alexander’s generals, had both Roxana and her son poisoned, ending Alexander the Great’s bloodline for good.