Loopholes Archives - Page 10 of 18 - Think Outside the Tax Box
By Tyler Menzer, CPA, PhD

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.

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TAX COURT ROUNDUP – September 2023

This roundup will spend a lot more space than usual on one story, because it’s the biggest of the year in Tax Court so far...

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Tax Court Roundup – August 2023

The dog days, the doldrums, the get-out-of-town days...they're here. The United States Tax Court is not immune, as the blockbuster cases and newsletter headliners have largely vanished. Still, there are report-worthy stories, despite the call of seashore and mountain meadow.

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Cautions in Tax Research — Finding True Guidance

The tax research process continues to grow increasingly complex for numerous reasons. This article notes several of these reasons and offers tips for your tax research process to be sure you have the latest appropriate guidance for answering tax questions and taking properly supported positions on tax returns.

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TAX COURT ROUND-UP JULY 2023

Here's the latest filings and tax court cases for July, 2023!

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Tax Court Roundup June 2023

This month I've decided to change format. I'm grouping Tax Court thumbnails by category. Not every reader deals with every issue. But coverage is still useful even where only a few specialize. Click here to read the latest happenings!

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Famous Bad Citizens and the Code That Caught Them – Al Capone

At its peak, Alphonse (Al) Capone’s criminal empire was worth approximately $1.3 billion when adjusted for inflation. On June 5, 1931, Capone was indicted on multiple counts of income tax evasion. At the time the maximum penalty for his offenses was 32 years in jail and $80,000 in fines (almost $1.6M in inflation adjusted dollars). The prosecution in Capone’s case “documented Capone's lavish spending, evidence of a colossal income. The government also submitted proof that Capone was aware of his obligation to pay federal income tax but failed to do so." Click here to keep reading about this fascinating case…

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Tax Court Roundup – May 2023

As always, much has happened in the tax courts this past month; let's jump right in!

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Key Lessons from 2022 Tax Rulings

This article does not summarize key rulings of 2022, but instead offers some key lessons and reminders from 2022 tax opinions as well as a few IRS rulings. If you want to read the ruling, see the citations and links. Takeaways from a few state tax rulings that have a lesson of relevance beyond the particular state are also included...

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