According to our divorce agreement my ex-wife if liable for the first $250.00 of medical expenses that are not covered by insurance each year for each child. She has refused to pay the doctors and I have had to pay in full for each child. Also, we have unpaid IRS debt incurred from previous returns that she refuses to pay her portion of. I am directed to pay her a monthly property settlement amount for a joint business held during the marriage. Can I deduct any or all of these fees from my monthly payments to her? This is above the alimony and child support payments.
The proper course of action is to file a Motion with the court asking that your ex-wife be held accountable for failing to fulfill her responsibilities in accordance with the Judgment of Divorce, i.e. that she be held in contempt of court and/or violation of litigant's rights, and go on to ask that you be made whole, whether by her forwarding reimbursements to you or you being allowed to withhold payments due to her until you are made whole.
The alternative that you propose is self-help. While that may be effective, if your ex was to file a Motion to find you in violation of the terms of the agreement she may be successful. That is why you best course of action is to bring the issue before the attention of the court and ask the court to make you whole.
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I think you'd be safe deducting it, but make danged sure you're 100% right and send her a letter (Delivery Confirmation Mail) explaining why you're making the deductions and setting out the math. If you're wrong and she files for enforcement, you'd probably be hit with her counsel fees, so be sure.
IF YOU LIKE THIS ANSWER AND APPRECIATE THE TIME IT TOOK TO WRITE IT, PLEASE SELECT IT AS "BEST ANSWER." Thanks. The above is said without seeing your case file and without my understanding the entirety of the facts of your case. Depending on those facts, the above information be may incomplete or may be completely inaccurate. The above is intended as general information only based on what you described and not as legal advice. I advise you to consult with counsel who may be able to provide better information commensurate with a better understanding of your situation.
You need to consult with an accountant to be sure you can make any Schedule A deductions on your Form 1040.
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