Chief Counsel Advice Memorandum Debunks Tax Avoidance Scheme Using Trust

In a recent Chief Counsel Advice Memorandum[1] (“CCM”), the office of the IRS Chief Counsel debunks the income taxation, or lack thereof, found in promotional materials promoting a structure known as a “Non-grantor, irrevocable, complex, discretionary, spendthrift trust”, with a note that the structure may be referred to by several other similar but slightly different…
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Non-Recourse Debt Forgiveness Bites Shareholder Upon Forgiveness

How is relief of debt treated for tax purposes? Does it matter if the debt is recourse or non-recourse? Does it matter if the debtor is a separate entity guaranteed by the owner(s)? Does it matter if the debt is forgiven as part of a sale of property securing the debt? These issues were addressed…
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Your Estate Plan and Life Insurance – A Complementing Pair

It is estimated that approximately 52% of all Americans have some form of life insurance. On the other hand, there are also estimates that only 27% percent of Americans have some form of an estate plan in place. This article provides a brief and simple overview of how the two are not mutually exclusive, and…
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Gage – Cashier Check Timing Case

We have covered timing and delivery issues in several articles, such as the recent Demuth and Hoensheid cases.[1] Similarly, the recent Tax Court case of Gage v. Comm’r dealt with the taxpayers that believed they paid a $875,000 settlement to the Department of Housing and Urban Development (“HUD”) in December of 2012.[2] Unfortunately for the…
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Tax Effect of Protocol Updates to Blockchain-Based Cryptocurrency

A recent Chief Counsel Advice Memorandum (“CCA”) discusses certain tax consequences pertaining to a taxpayer owning cryptocurrency native to a blockchain that undergoes a protocol upgrade. CCA 202316008. In the hypothetical scenario discussed in the CCA, a hypothetical blockchain, very similar to Ethereum, underwent a change in the method in which it approved and processed…
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2023 Dirty Dozen List

Every year the IRS publishes its list of the top tax scams that taxpayers should be aware of, known as the Dirty Dozen. I discussed the IRS’s 2021 Dirty Dozen list in a prior web article,[1] and the IRS has recently released its 2023 Dirty Dozen list.[2] Several of these scams are designed to steal…
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Hoensheid: Assignment of Income and Gift Substantiation

It is fairly common to make charitable gifts of property prior to a sale transaction. Often, those gifts are of real property or closely-held business interests. This is for good reason. Structured properly, not only do donors generally receive a charitable income tax deduction equal to the fair market value of the donated property, they…
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