What is your Business Worth? Buy-Sells and the Connelly Case

Is your business worth more to the IRS than it is to you? Will you owe estate tax on more value than you receive? A recent tax case illustrates how this is possible.[1] It is very common, even advisable, that closely-held business owners enter into buy-sell agreements limiting transferability of interests and setting forth procedures…
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Court Says No to IRS Attempt to Aggregate Gifts for Discount Purposes

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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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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Injunctive Relief Hiding in Plain Sight? CIC Services, LLC v. IRS

So, we did not write on the first District Court case which was a loss for CIC Services, LLC (“CIC”) and Ryan, LLC(“Ryan”), the Plaintiffs. But, a Supreme Court decision gave the Plaintiffs another bite at the apple. This case involves Notice 2016-66 (“Notice”), the older-sibling notice to Notice 2017-10, in which micro-captive insurance transactions…
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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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Original Characterization by Taxpayers Matters, Even When Reporting Improperly

In an ongoing breach of contract case,[1] in which the parties contested the treatment of certain transfers as either gifts or as compensation under a contract, the U.S. District Court of Arizona dismissed the portion of the plaintiff’s motion for summary judgment related to “gift tax damages” due to the fact that gift tax labilities…
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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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Directions

[**Practice Alert: Corporate Transparency Act is Here: What You Need to Know**](https://esapllc.com/practice-alert-cta-mar-2024/)
[**Practice Alert: Corporate Transparency Act is Here: What You Need to Know**](https://esapllc.com/practice-alert-cta-mar-2024/)