We actually READ the book of Judith for Hannukah. I will attempt to summarise.
Nebuchadnezzar is the autocratic emperor of Assyria and (realistically) rules a vast swathe of territory and (unrealistically) thinks that he is almost a god. This isn't THE Nebuchadnezzar, not any of the other Nebuchadnezzars either. Stories of the time apparently just slap the Nebuchadnezzar label on rulers who are going to be bad news, reflecting that the people who wrote the stories which we're reading were first, people in Jerusalem conquered by Babylonian Nebuchadnezzar and deported back to Babylon, then their descendants who later returned to Israel. Fictional Nebuchadnezzar has a massive beef with Some Ruler who doesn't really come into the story after the first chapter.
There is detail about Some Ruler's fortified cities (wall width, size of stones, gate size, number of towers), which having recently read
https://acoup.blog/2021/10/29/collections-fortification-part-i-the-besiegers-playbook/ was pretty interesting from a historical-strategic perspective. A wall like that shuts off raids from any any army less professional and determined that what the emperor of Assyria can muster.
Narrator: This is what a walled city protects against, and this is what it doesn't.
Not-Nebuchadnezzar summons armies from all of his tribute territory, all the way west through the middle east to Egypt and Ethiopia to come make war on Some Ruler. They say, "no, we've tried going to war for causes we don't care about, it sucks, screw off." He says, "do it anyway". They say, "you and what army".
Then he summons a giant army from the territory which does respond to him, and crushes Some Ruler. Then he swears by his throne that he will totally make all those territories west all the way to Egypt sorry and stab them with his own sword. Then he summons his important general Holofernes and says, "It's murdering people who don't do what I say day, go west and kill everyone you find in such a way that I get the credit" and Holofernes is "yes sir".
Narrator: There's a count of infantry and cavalry and (implicitly) a lot of unequipped hangers on. This is how you organise armies. Also a LOT of supplies. Also a lot of gold.
Holofernes marches west and kills and ravages and burns until some countries come begging to let them worship Fake-Nebuchadnezzar afterall. Then he's like "we've conquered everyone," and someone is like, "yes, everyone apart from the jews in the hill country where it's hard to march armies" and he glares at them and takes his army off to conquer them too.
Someone explains that those people are protected by God and it's impossible to conquer them, unless they screw up and offend God somehow and God lets it happen.
Narrator: SO DON'T OFFEND GOD, OK? ARE YOU LISTENING AT THE BACK?
Holofernes is offended by this so he sends Someone up into the hill country as punishment, vowing to kill him along with everyone else. Some other suck-ups tell him that the hills are bad for armies so he can't force the outnumbered defenders into a pitched battle, but if he can camp the right water-supplies the people will eventually have to surrender.
Narrator: This is why in the present we're so careful to maintain the spring and the cisterns and everything. THIS MEANS YOU, MR POPULAR FRONT OF JUDEA.
So, the country is besieged, especially the poorly-attested town where a young, industrious, pious, admirable woman called Judith lives. Her husband had died, but she continued to run their estate very efficiently, and do lots of pious things.
Narrator: blah blah piety blah
The situation got worse, and there was much debate about "OK, we've been observant, God will save us, but we've rationed water for weeks and people are starting to die, WHEN will God save us, is there a point where we should surrender anyway".
Judith said, this won't do, I'll fix everything. And she went to the town leaders and told them to follow her plan and she would go and deal with the army by herself. And because (a) this is a story (b) they were desperate (c) she was very pious and seemed like God would approve of her and (d) they didn't want to go fight the army themselves.
So she mourned and prayed some more, and then bathed and put on the best finery she only wore for special occasions, and took one maid with a supply of kosher-slaughtered food, and boldly marched down to the army.
Army: Why are you here?
Judith (cunningly lying): The desperate town leaders are going to start eating the tithed grain set aside for God and the priests, or just outright surrender. They are no kin to me any more, take me in!
Judith: And take me to your Top Man because I can tell him how to conquer the town, and the whole country. Only him.
Narrator: This is why you NEVER NEVER eat the tithe set aside EVEN WHEN an army is besieging you.
And the scouts politely captured her, but finding that all very plausible, and also noting that although she hadn't made a point of it, she was very good looking and the sort of woman Holofernes liked hanging out with whether or not he got any Key Military Secrets out of it, very politely took her to Holofernes who was just as delighted to receive her as everyone said.
And they had some quiet dinners, and Judith was very careful to ensure that they both had fine refreshments, but she only ate the kosher food.
Narrator: Only eat kosher food.
And Judith explained, that the leaders were going to abandon God, and when they did, God would let the army attack safely without protecting the defenders. But she added, she was still pious and God would let her know when that happened. All she had to do was go outside the camp to pray last thing at night, and listen for God's response.
Narrator: Outside the camp. Remember, that's important foreshadowing.
So they did this a few nights, with Judith talking with Holofernes, and him becoming increasingly smitten with her, but her also saying, maybe tonight is the night you get to attack.
And eventually he talked her into a private dinner, where she was very solicitous of his comfort, and they drank wine, and he drank A LOT and fell fastly asleep.
Narrator: Pay attention, this next bit's clever.
And she drew his sword from his scabbard and hacked his head off as hard (and quickly and quietly) as she could.
Narrator: OK, maybe actually the clever bits were all the earlier bits. This bit wasn't exactly clever, just very effective and satisfying.
Then she left the tent (possibly suffering a bit of ribaldry from the guards) and her maid hid Holofernes head in the empty kosher food bag, and they left the camp (ostensibly to pray, as she had each previous night and Holofernes had given permission for.)
And as soon as she was out of sight, they dashed up the hill to the defenders and said they'd returned. And everyone celebrated. And then all the men timed a big attack in the morning which led to Holofernes army first, forming up in triumph that they'd destroy them in a face-to-face battle, but then panicking when they realised that the general's head had vanished in the night and appeared on a spear over the defender's camp. And the army was driven away or killed.
And God was like "Nyah, Nebuchadnezzar, you thought you were almost divine, but your macho army totally fizzled, and I struck it down with nothing more than a single determined, personable, pious woman."
This all alludes to the more genuinely historical invasion by the Greek Seleucids repelled by the Maccabees, so it is celebrated in Hannukah, along with the later tradition that one of the things Judith specifically plied Holofernes with was good cheese.
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