Private Jet Charitable Deduction Fails for Lack of Substantiation

Cases, Charitable Giving, Court of Appeals, Income Tax, Tax, Tax Controversy

In Izen v. Comm’r, the Fifth Circuit Court of Appeals recently affirmed a Tax Court decision to deny a taxpayer’s charitable contribution deduction where the taxpayer failed to meet the statutory documentation requirements for the charitable contribution.[1] The key documentation that the taxpayer lacked was a contemporaneous written acknowledgement that included his taxpayer identification number.…
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Deductibility of Son-in-Law’s Tuition Expense

Cases, Income Tax, Tax, Tax Court

In the recent Tax Court Opinion of Sherwin Community Painters, Inc. v. Comm’r, a corporation was denied a Section 162 business deduction for amounts paid for the boyfriend of the sole shareholder’s daughter to take a course in coding.[1] Gray Edmondson discussed the importance of being in a trade or business years ago, one of…
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Fab Holdings – It is called the “Tax Plan”

Cases, Income Tax, Tax, Tax Court

In another recent case involving a multi-entity tax savings strategy, pitched as the “integrated tax plan,” particularly leveraging “management fees,” we see again the Tax Court scrutinizing the legitimacy of the structure, incorporating a C corporation and a partnership, and in turn allowing the IRS to whipsaw the taxpayers.[1] Facts Around late 2009 through early…
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Heiting and the Claim of Right Doctrine

Cases, Court of Appeals, Income Tax

In the Heiting v. United States[1] decision issued on October 18, 2021, the United States Court of Appeals for the Seventh Circuit affirmed a district court decision[2] to dismiss a couple’s claim for a refund of taxes, rejecting the taxpayers’ argument that the repurchase of restricted stock previously sold by their trustee was effectively a…
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Court Says No to IRS Attempt to Aggregate Gifts for Discount Purposes

Cases, District Court, Estate and Gift Tax, Estate Planning, Tax, Tax Controversy

In a recent case out of the United States District Court for the District of Connecticut, the Court denied the IRS’ motion for summary judgment and refused to aggregate the gift of partial interests in real estate together for purposes of valuing the gifts and thus determining appropriate discounts.[1] The IRS alleged that no discount…
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