Considering how soon Halloween comes after October 15, the extended due date for individual returns, having a tax horror story seems really appropriate. The horror story came out on October 24, with the Eleventh Circuit decision in the case of Lee v U.S. Dr. Wayne Lee seemed to have done everything right to be in compliance. His estimates overpaid his taxes every year, and he would let the refund ride into the next year. He hired a CPA to prepare his returns and dutifully signed and sent the CPA Form 8879 IRS e-file Signature Authorization. He did this for his 2014, 2015, 2016, and 2017 returns. Then disaster struck.
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.
