Feature Article

Yes, the IRS does forgive some tax penalties. The IRS refers to this forgiveness as penalty abatement. Abatement is the act or process of reducing or removing something. In this case it is removing or reducing a penalty. But penalty forgiveness is not a blanket offer that everyone qualifies for the way the radio ads make it seem. There is a process that the IRS has for requesting and granting abatement. It is up to the taxpayer to prove that they qualify for abatement. That’s where you come in.

In a recent turn of events that has caught the attention of financial experts and policymakers alike, Senate Finance Committee Chairman Ron Wyden, D-Ore., has unveiled the results of an 18-month investigation into the use of Private Placement Life Insurance (PPLI) by the ultra-wealthy. The investigation, the first of its kind focusing on PPLI, highlights the use of these policies as a significant tax shelter mechanism, revealing the ways in which a small number of wealthy individuals are leveraging them to avoid substantial tax liabilities.

Twice in my four-decade career, two special agents from IRS Criminal Investigation (CI) entered my office armed with a search warrant, firearms at their side. In both cases, it started the same way.

For wealthy families, the world of finance can feel like a high-stakes chess game. With increasing state and federal income tax rates, new tax laws on the horizon, and the complexities of private investments like hedge funds, finding ways to grow and transfer wealth efficiently is more important than ever. Enter life insurance—a tool not just for its traditional role of providing death benefits but as a strategic ally in tax-efficient wealth management. In particular, Private Placement Life Insurance (PPLI) offers unique advantages that make it a worthy consideration for those with sophisticated financial needs and significant liquidity.

In Matt Metras’ excellent article on tax reporting for clients who receive settlements from the Celsius bankruptcy, he says “It’s unclear if this section could apply to digital asset bankruptcies for a variety of reasons outside the scope of this article.” Matt provides an example of the IRS’ preferred method of accounting for settlement proceeds as published on the Taxpayer Advocate’s website. Matt also notes that the TAS tax tip lacks any citations to substantial authority. It may or may not be taxpayer friendly. The articles published by many cryptocurrency exchanges are also citation free and, after a cursory review, seem geared in a larger sense toward helping exchange users account for the settlement accurately on the exchange itself. In this article, I would like to look at the forest of tax law principles that the Celsius bankruptcy settlement puts into play rather than any specific tax reporting tree. Welcome to the jungle.

Why is the freezing point of water 32 degrees? It was a fairly arbitrary decision made by inventor Daniel Gabriel Fahrenheit in 1724 and demonstrates that Americans will do just about anything to avoid using the metric system. But this isn’t a story about Fahrenheit, it’s about Celsius. Celsius was a major cryptocurrency exchange founded in 2017, which at its peak had over $12 billion in assets under management. Celsius declared Chapter 11 bankruptcy on July 13, 2022. Celsius found itself caught up in the major crypto collapse of 2022...

Creativity on a tax return is a natural tendency. Many strategies and behaviors we know are wrong, e.g. not reporting all income. However, is it ever okay to disregard some deductions and pay more tax? At first glance, it would seem that the IRS should like the idea of more reported income and a higher tax liability attached to the additional income. The IRS does not.

Misinformation, misinterpretations, and catastrophizing – much has been written these past few months about BOI (Beneficial Ownership Information), all coming from a range of voices, from tax professionals to politicians. There have been dire predictions of small business owners being ushered to jail for failing to file and fears of tax professionals rounded up for the unauthorized practice of law (UPL). Then there are those who mistakenly say BOI has been ruled unconstitutional and who reject any need to worry about it. That is profoundly wrong. Let’s look at the facts and put an end to all of this fearmongering.