Albert Lauber, my favorite Tax Court judge, gave us an opinion in February that paints a detailed picture of the workings of a syndicated conservation easement. In the end, he supports the findings of the Senate Joint Finance Committee that the engine of these abusive transactions is an inflated appraisal. In November, David Gustafson issued an opinion that exposed the financial engineering techniques that promoters engaged in. We’ll take a look at those, but first I would like to give you an overview, because we may need that to figure out the lessons to be learned.
Tax Loss Harvesting with Cryptocurrency
Tyler Menzer, CPA, PhD
In the Fall of 2025, Bitcoin reached an all-time high of over $120,000. Since then, it fell over 40% to under $70,000 in the first quarter of 2026, before slightly recovering, currently resting around $75,000 as of this writing. With the steep drop in the price of Bitcoin and other cryptocurrencies, a common question from taxpayers is whether they can use the current losses to offset their other income. Large investors and professionals such as Grant Cardone and Shehan Chandrasekera (Head of Tax Strategy at Cointracker) have suggested that cryptocurrency can be sold and bought back immediately to claim the tax benefits. As with most things, the answer to this is not as simple as they portray, and many commentators, influencers, and sometimes professionals, miss the intricacies of cryptocurrency taxation.
