The Estate of Thomas H. Fry v. Commissioner is an opinion that anybody who deals with S corporations needs to know about. You may have read about it as a taxpayer win and it is. Another reading is that it is a cautionary tale to not do what Thomas H. Fry and his team did with his S corporations, Crown Disposal Inc (CD) and CR Maintenance Services Inc (CRM). Think of the win part of this opinion as a life jacket that might come in handy if you run your ship into the rocks. Better you should pay attention to the rocks and avoid them.

Tax Loss Harvesting with Cryptocurrency
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.


