Before you get too deep into some of the complexities, let's make sure you have a good understanding of some basic terminology and rules regarding a 401k rollover.

Federal Withholding

Most often the money held in a 401k consists of pre-tax contributions.  Because this money has never been taxed, the federal goverment requires that distributions from retirement accounts have taxes withheld.  Your personal tax rate doesn't matter in determining the amount withheld--funds are automatically withheld at the rate of 20% of the distribution.  
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