Goodbye, Chevron – Loper Bright Enterprises

As tax planning practitioners, we do not typically see issues we deal with daily become the subject of cases before the United States Supreme Court. This term, we had the Connelly[1] case involving estate tax valuation of a decedent’s stock in a corporation funding a redemption buy-sell with corporate-owned insurance. Shortly thereafter, the Supreme Court…
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Revisiting Intrafamily Loans – Bolles

The Ninth Circuit Court of Appeals recently affirmed a Tax Court opinion dealing with the effect of lifetime transfers by a mother (Mary) to her son (Peter).[1] At issue was the nature of those transfers. On the one hand, Mary Bolles and her estate argued that the transfers constituted loans from Mary to Peter. On…
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Successor Trustee Liability for Unpaid Estate Tax

In a previous writing, I discussed the potential of an executor to be personally liable for a decedent’s tax obligations.[1] That discussion was based on lessons learned from a Tax Court opinion,[2] outlining certain steps for executors to consider in minimizing exposure to such personal liability. In 2023, in a split decision, the Ninth Circuit…
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Crider Trust Case – The Case for the Cautious Fiduciary

On February 8, 2024, the Mississippi Supreme Court issued its opinion[1] regarding an issue of first impression regarding Mississippi’s Principal and Income Act of 2013 (the “Act”).[2] As a worthwhile note, the Court noted that this is an issue of first impression and acknowledged as well as appeared to oblige the parties so as to…
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GSS Holdings – A Reminder on Economic Substance and Step Transaction

Most tax law is made up of very detailed statutes, regulations, case law, and other guidance. Layered on top of that body of law are a number of “judicial doctrines” that seek to serve as a backstop to formalistic analyses that could result in unintended tax results, allow taxpayers to place the form of transactions…
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Evaluating the Landscape: Impact of CIC Services, LLC Case on Attorneys’ Fees and Government Fairness

The recent opinion from the United States District Court, Eastern District of Tennessee, continues the saga of the case of CIC Services, LLC (“CIC”) and has implications for taxpayers seeking to recover attorneys’ fees under the Equal Access to Justice Act (“EAJA”) and for its broader reflections on governmental fairness, particularly those looking to challenge…
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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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