re: ESOP STOCK

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pre tax money or after tax mone

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Not necessarily

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You may need to talk to a CPA to find out. There are special rules for ESOP's that may affect you.

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But definitely this. Company stock inside an employer sponsored retirement plan can generate NUA and be distributed solely from the plan after age 55, receive no penalty, the basis be taxed as income and the gains be taxed as a cap gain. You definitely need to talk to someone about your situation and plan before you do anything though.

Ex. You retire from Apple with $500k of Apple stock. Say $50k is the basis and $450k is cap gains. You could make a distribution of all that and pay income on the $50k and a much more favorable Cap gains rate on the $450k.