You will enter both the W-2 and the 1099-MISC. Lawsuit settlements often include both back wages and other damages.
Regarding the W-2 with blank box 1, you can check with the employer to confirm it's correct. You won't be able to e-file with a W-2 that is blank in box 1. See this article for more details. TurboTax will provide instructions to print and paper-file the return if that becomes necessary.
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