Recent CCA Addresses Valuations

The IRS Office of Chief Counsel recently issued CCA 202152018 (“CCA”), in which the IRS is attacking yet another business valuation.[1] The IRS takes the  position in the CCA that because the valuation used failed to account for a potential acquisition, the grantor retained annuity trust (“GRAT”) failed to properly qualify as a GRAT even…
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Michael Jackson’s Estate, Valuation Battle of the Century

In May of this year the U.S. Tax Court issued a memorandum of opinion on the value of several assets included in the Estate of Michael Jackson (“Estate”) for federal estate tax purposes.[1] This opinion comes more than a decade after Jackson’s death in June of 2009 and provides some resolution (albeit subject to appeal)…
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Taxpayer Denied Contribution Deduction to Sole Proprietorship Profit-Sharing Plan for Income Paid Under Deferred Compensation Plan of Prior Employer

In a recent Tax Court case, a taxpayer was denied a contribution deduction for income paid into a sole proprietorship profit-sharing plan when the Court determined that such income had not been derived from the trade or business with respect to which the plan was established.[1] Rather, the income was paid to the taxpayer under…
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IRS Demands iTunes Cards? Beware the Dirty Dozen!

In January of 2002 the Internal Revenue Service (“IRS”) issued a press release highlighting a dozen different tax scams and encouraged taxpayers to “maintain national vigilance.”[1] This list was dubbed the “Dirty Dozen,” and the IRS has continued to issue similar press releases containing updated lists of purported tax scams for taxpayers to be on…
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Executor Liability for Decedent’s Tax Obligations

A recent Tax Court opinion[1] highlights one of the risks of serving as executor or administrator of an estate, potential liability for a decedent’s tax obligations. The case involves application of the federal priority statute[2] applicable to fiduciaries.[3] That statute provides, in relevant part, that “a representative of a person or an estate (except a…
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Blossom Day Care Centers – The Income Tax Side

Last week, Charles Allen wrote about Blossom Day Care Centers, Inc. (“Blossom”) and its owners regarding their employment tax case.[1] Frequently, we write articles intending to remind readers of the importance of substantiation, especially in the income tax world. In reviewing Charles Allen’s article, I kept finding myself wondering about the income tax implications of…
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Deny It Like It’s TOT – Conservation Easement Denial Upheld

It is no secret. Everyone likes reading and writing about syndicated conservation easements. In December 2019, the Tax Court ruled in the case of TOT Property Holdings LLC v. Comm’r.[1] The result was an unfavorable one for the taxpayer. The transaction in question was more-or-less a run of the mill syndicated conservation easement, albeit ending…
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Entities and the Performance of Personal Services: Berry

Owners of legal entities typically establish those entities to achieve certain planning goals, be them tax, asset protection, contract management, or other reasons. Key to accomplishing those goals is that courts respect the entity planning structure that is established. In the recent Tax Court opinion of Berry v. Commissioner[1], we see a taxpayer who intended…
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