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> lost the wallet and wishes he were dead

At least it's a good tax write-off. (Well… $3000 a year for life in the US iirc.)

What’s stopping me from claiming I had this (or any other) wallet and getting the write off?

Audits, same as anything else.

What I mean is how would I prove that I once possessed the key to a wallet?

Why, are you taking notes on how to perform a criminal conspiracy?