1) How should legal settlements be reported if the payment request is joint, in the name of an executor and law firm? 2) Should a former employee receive a 1099 for payments related to lawsuit for physical injury?


Regarding settlement payments, it depends on whether the settlement is reportable to the plaintiff or not—it is possible that you will have to issue two 1099s, one to the attorneys and one to the plaintiff.  On The AP Network see: Demystifying Form 1099 for Legal Settlements.

Regarding your second question, per the article reference above and IRS instructions, if the settlement was for damages only (medical costs), no, it is not reportable; but if there were punitive damages awarded, that is reportable. See IRS Instruction for Form 1099-MISC, page 6 (in the section on Box 3, which begins on page 5).

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