Something old, something new, is the usual product of Tax Court, and this month is no exception. New: Equitable tolling is applied to out-of-country petitioners (maybe), an abandoned corporate merger escapes Section 1234A capital loss treatment of a break-up fee, the discounted cash flow method of valuation is rejected for valuing conservation easements, and the S.E.C. v. Jarkesy Eighth Amendment controversy continues. Old: Erroneously addressed Notices of Deficiency, witness testifying remotely, sealing witness testimony, CDP is a snapshot, and debt-vs-equity.
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.
