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Do you pay tax on a winning settlement in a lawsuit?

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This depends on what the settlement consist of. Any part of the settlement that is reimbursement for medical expenses or pain and suffering is not taxable. If part of the settlement consists of reimbursement for lost wages, that is taxable. That is because, had you received those wages back then, you would have had to pay taxes on them. It is basically taxable money that you didn't get till after you should have.
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