Not a good idea. He will owe interest, and penalties including the failure to file penalty and failure to pay penalty. This is a foolish game he is playing. In the end the IRS will win this game and he will lose and lose big time.
A prenuptial agreement if properly drafted and followed should protect your family. However, your father could have been more genereous than the agreement required and that is usually permissible under the agreement. Make sure there was no undue influence or duress if this was the case. You need to have this agreement and the situation reviewed by an estate attorney to be sure of where your family stands.
Your dad's will once probated is a matter of public record. The step mom's will is a private document that you have no right to see.
Hope this helps.
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There is no good outcome from not filing.
He can either file or not. If not, then he faces the consequences of not filing with the state and federal revenue authorities. There is no effect on his child support obligation.
If he does file, he will either owe taxes or be due a refund. He will owe the taxes whether he files or not. He may mitigate the penalties by filing even if he does not pay.
If he is due a refund, he will not receive it unless he files. However, the refund could be intercepted to pay his child support arrearages. At least if he does file, the refund goes against the arrearage, to his benefit, and will be paid to the child, to the child's benefit.
There appears to be no benefit from not filing and a possible benefit from filing.
I absolutely fail to see the logical point in not filing taxes (where "failure to file" is a federal crime) because of owing back child support.
If it is because he is afraid that if he files the tax return, the child support enforcement agency will find out where he works and then garnish his wages, this is going to happen anyway! His employer is required to file a copy of the W-2 with the IRS and the child support enforcement agencies have access to these records.
For the same reason, if he is not filing a tax return because he has not money left to pay taxes that he owes, the IRS will receive a copy of the W-2 information from the employer and calculate the taxes he he owes for him (but without consideration of deductions that he may be able to take against that income) and will send him a bill for those taxes (plus penatlies and interest). Not only won't he be able to avoid the taxes he owes (plus penalties and interest), but he will also again be guilty of "failure to file".
If he is not filing because he is entitled to a tax refund and does not want the refund intercepted by a child enforcement agency, then this really does not make any sense. If he doesn't file, he doesn't get any refund. If he does file and the refund is intercepted for child support arrears, then he still does not get the refund BUT his child support arrears will be reduced by the amount of the refund.
If in fact he is paying "all" of income toward child support, then he really should file for a modification of child support. If all of his income is being withheld by the employer pursuant to an Income Deduction Order for child support, then he should also include in his petition a request for a modification of the IDO. In accordance with federal law, the maximum amount that is permitted to be withheld from income is 65% (not 100%).
Your boyfriend should contact a local attorney immediately to discuss his situation in sufficient detail so that he may receive the appropriate and necessary legal advice for his particular situation and make timely arrangements to either get his taxes done and post-marked today or at least file for an extension.
This response does not create an attorney-client relationship and is intended for general information purposes only.