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The book of Lamentations

That’s a strange way to look at it: how could the total ruin of God’s beloved people and the city have anything worse?

The message throughout is that Jerusalem, the last man standing, so to speak, of Israel had sinned as badly as the rest, and was now facing the consequences:

Lamentations 1:8Jerusalem has sinned gravely,
Therefore she has become vile.
All who honored her despise her
Because they have seen her nakedness;
Yes, she sighs and turns away.

Everyone and everything is trampled and mourns: the roads, the priests, the young women, the city gates, the children, the army, the young mean, the rulers, and so on. Worse still, there is no one to comfort them.

Lamentations 3:52-54 My enemies without cause
Hunted me down like a bird.
They silenced my life in the pit
And threw stones at me.
The waters flowed over my head;
I said, ‘“I am cut off!’

Then, in the depths of that despair, there is hope:

Lamentations 3:55-59 I called on Your name, O Lord,
From the lowest pit.
You have heard my voice:
Do not hide Your ear
From my sighing, from my cry for help.
You drew near on the day I called on You,
And said, ‘Do not fear!’
O Lord, You have pleaded the case for my soul;
You have redeemed my life.
O Lord, You have seen how I am wronged;
Judge my case.

We’ll never know for sure what Jesus went through in those days between being arrested and resurrected; but this helps us imagine the total loss He must have encountered.