I have a huge Cast Iron Wash/Stew Pot

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Turns out it doesn't leak.

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So why would you drill a hole in it?

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So why would you drill a hole in it?

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So rain water will drain. It's at a memorial site way back up in the woods.

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If that thing is really old, and in decent condition, you might want to see what it's worth before you punch a hole in it.

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It has family sentimental value and is at the family memorial site. It's going to stay there at least as long as I have breath.

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Then by all means, find the best way to punch a hole in it.
I would do the same. I thought you said it was given to you by someone else. Must have misread your OP.

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By a 1st cousin, it was his parents (who have been dead for many years). Don't know the history prior to that. We have other similar pots in the family for family get togethers.

Then why ruin it and not clean it up and continue passing it down the line? It would be terrible to see something like that just rot away when a part of your family could live on forever

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It's going to live on forever in the family memorial spot. We have others we use for cooking, this one hadn't been used in decades and was so rusted I wouldn't use it to cook.

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Not trying to talk you out of using it as a memorial but the rust is no reason to abandon it for cooking if you weren't going to repurpose it. Rust, even really bad rust, is very easy to deal with on cast iron pots.

Also keep in mind that it may only leak when heated so it may still have a crack, just not one that leaks at ambient temperature.

Drilling into cast iron is not hard but, as another poster noted, just go slow and if you drill one or two holes, you may not even want to use a lubricant or cooling fluid. Any bit that is designed to drill into metal will do, the surface hardness of cast iron is not particularly high. here is a link to an article about drilling cast iron.

https://www.hunker.com/13403041/how-to-drill-into-cast-iron

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Not trying to talk you out of using it as a memorial but the rust is no reason to abandon it for cooking if you weren't going to repurpose it. Rust, even really bad rust, is very easy to deal with on cast iron pots.

Also keep in mind that it may only leak when heated so it may still have a crack, just not one that leaks at ambient temperature.

Drilling into cast iron is not hard but, as another poster noted, just go slow and if you drill one or two holes, you may not even want to use a lubricant or cooling fluid. Any bit that is designed to drill into metal will do, the surface hardness of cast iron is not particularly high. here is a link to an article about drilling cast iron.

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I'm going to look into your not leaking until heated theory, that's interesting.

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The thermal expansion of the pot may cause the crack to open enough to leak where it would not otherwise.

It is a known phenomenon in heated equipment, though not really common, and actually both ways. Some things leak like a sieve until heated and it's expected to happen with drip pans to account for it, obviously in a situation where this creates a minimal hazard.

Sometimes it's even weirder in that it is fine at ambient and fine at operating temperature but leaks as things are heating up due to varying thermal expansions. Obviously, that would not be the case with a pot.

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U2s would leak like a sieve on the ground (there'd be drips all under them), but they'd be fine inn the air.