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Hi sorry for the lack of info. spouse and self are 34 yo, filing jointly, no other income. We are not affected by AMT.

Using your numbers (recognizing that they're only approximations) either you have $40K of taxable income (before personal exemptions) without the withdrawal/charitable contribution or $50K of taxable income (before personal exemptions) with the withdrawal/charitable contribution. Your error was in thinking that the $20K contribution would add to the $10K standard deduction. It doesn't; it replaces it.

Add to this the $2000 penalty for early distribution from your IRA, similar addtional taxes and penalties at your state level and the loss of $20K of assets which you should be saving towards your ultimate retirement and this doesn't seem like a very wise idea.

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