Astor To Philip's Right Eye (The Re-Take)

The Time King Philip II of Macedon Got an Arrowgram to the Face

By Mike Walk

Let us now turn to the exciting, deeply weird, and highly relevant world of ancient Macedonian military history, which you probably slept through in school because it did not involve lightsabers or any actual Macedonians you could name besides Alexander the Great, who, fun fact, was great.

But before Alexander came along and conquered most of the known universe using only charisma and an army of extremely jacked men in skirts, there was King Philip II, his dad. Philip was a big deal in his own right: a one-eyed, heavily mustached king who invented phalanx warfare and possibly dad jokes.

Our story begins in Methone, a city which Philip was trying to conquer, because in those days kings didn't have hobbies like pickleball—they just randomly attacked cities to stay in shape.

So Philip is out there doing his thing, probably shouting about battering rams and looking regal, when an arrow suddenly flies from the ramparts and plants itself directly into his right eyeball. This was back in the days before OSHA regulations or safety goggles, so this sort of thing happened more often than you'd think.

Naturally, the royal staff removed the arrow from the royal eye socket, possibly while screaming things like, “OH DEAR GOD,” and “DO WE EVEN HAVE A ROYAL OPTOMETRIST?” But then they notice something even more surprising: the arrow has a note attached.

Let’s pause and appreciate this. Somebody shot a notarized arrow into a king's eye. That takes petty vengeance to a level rarely seen outside of group texts and Renaissance weddings.

The note read:

“Astor to Philip’s right eye.”

This sounds like a Hallmark greeting from the Assassin’s Collection, but it turns out to be a full-blown murder-pun courtesy of a man named Astor, who at that moment became history’s most terrifying postal worker.

Digging further, we find that Astor had once tried to join King Philip’s army as an archer. He apparently told the king that he was so good with a bow he could shoot a bird in midair, to which Philip responded something like:

“Oh that’s helpful. Call me when I declare war on birds.”

This was a royal burn, the ancient Macedonian equivalent of being shamed on Instagram.

Feeling humiliated and thoroughly underrated, Astor decided to go full revenge mode and joined the enemy team, where he waited for just the right moment to demonstrate his “shooting skills" by destroying the king’s ability to see in 3D with one perfectly aimed, sarcastic arrow.

It was the ultimate flex: the world's first weaponized “I told you so.”

Historians aren’t 100% sure this story is true. It’s possible that Philip just tripped while juggling flaming swords, or was poked by an angry olive branch. But forensic scientists actually reconstructed his face based on his skull, and sure enough—he looks like Nick Nolte after a very bad day at archery camp.

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The Moral of the Story:

• Always be polite to archers. You never know which one has main-character vengeance energy.

• Sarcasm may be fatal.

• Ancient kings really needed to invest in safety goggles.

• History is full of men who lose body parts to prove a point.

And finally: never tell a guy who claims he can shoot birds in midair that he’s useless. He might just send you a flying message with extreme prejudice to prove otherwise.