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A relative died with old stock certificates. Is it possible for the heirs of the estate to write off this loss against any capital gain or ordinary income?

Quick answer - no. The heirs inherit the stock at its FMV as of the date of death. Any loss before then belongs to the decedent, and if the decedent has unused loss carryovers, they die along with the decedent. The executor of the estate might be able to use the loss on the decedent's final return, or amend any open years to claim the loss, but the loss stays with the decedent and can't be transferred to the heirs.

Also, is it possible to find out when these certificates became worthless and how much this relative may have originally paid for them? Does the face of the certificate offer any clues?

A stock broker could probably help you with the first part - when they became worthless. This is a place where a full-service broker earns his/her keep.

But as to what was paid for the stock, you'll have to dig through records to find that. There is likely an issue date on the face of the certificate. That will tell you when the certificate was issued. You can use that as a starting point in your record search. Basically, you'll need to start at that date and go back in time to find the purchase. The one thing you know is that the stock was purchased sometime before the issue date.


PS - What's the stock? Perhaps someone here can help.
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