Post-Settlement Tax Woes – Tillman-Kelly

Cases, Income Tax, Tax, Tax Court

In a recent case from the Tax Court, two married taxpayers failed to establish that their settlement proceeds fell within a statutory exception to taxation.[1] This case is a bit more straightforward than others we may write about from time to time. Factual Background In September 2009, Chicago State University (“CSU”) hired Mr. Bryant Tillman-Kelly…
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Taxpayer Loses Royalty Tax Case Appeal

Cases, Court of Appeals, Income Tax, Tax Controversy

In a recent appellate decision from the Ninth Circuit, a taxpayer/attorney/neurosurgeon/corporate shareholder who helped develop a patented imaging technology was held liable for ordinary income assessments with respect to annual royalty payments related to patent royalty income. Facts Dr. Aaron Filler, a licensed attorney and neurosurgeon, contributed to the development of a certain Diffusion Tensor…
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Fab Holdings – It is called the “Tax Plan”

Cases, Income Tax, Tax, Tax Court

In another recent case involving a multi-entity tax savings strategy, pitched as the “integrated tax plan,” particularly leveraging “management fees,” we see again the Tax Court scrutinizing the legitimacy of the structure, incorporating a C corporation and a partnership, and in turn allowing the IRS to whipsaw the taxpayers.[1] Facts Around late 2009 through early…
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Crypto at ESA

Business Transactions, Compliance, Current Events, Estate and Gift Tax, Estate Planning, Fiduciaries, Income Tax, New Legislation, Tax

Since we’re the cool, diamond-handed, trendy-loving, FUD(fear, uncertainty, and doubt)-crushing, FOMO(fear of missing out)-haters and at the same time professionals, now seems just as good of time as ever to discuss what we are doing at our firm to familiarize ourselves and become more competent in the ever-growing and evolving world of magic internet money,…
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Injunctive Relief Hiding in Plain Sight? CIC Services, LLC v. IRS

Cases, District Court, Income Tax, Tax Controversy

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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Blossom Day Care Centers – The Income Tax Side

Income Tax, Tax Court

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

Charitable Giving, Court of Appeals, Current Events, Income Tax, Tax, Tax Related Cases

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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