Will Microstrategy have to pay any federal income taxes on unrealised gains on its cryptocurrency holdings in 2026?
Will Microstrategy have to pay any federal income taxes on unrealised gains on its cryptocurrency holdings in 2026?
Basic
2
Ṁ20
2027
45%
chance

As reported by the WSJ:

After years of raising money through stock and debt offerings to buy bitcoin, MicroStrategy owns a stash worth about $47 billion, which includes $18 billion of unrealized gains. In an unusual twist, it could have to pay federal income taxes on those paper gains—even if it never sold a single bitcoin. The tax bill could total billions of dollars starting next year, according to a new disclosure this month by MicroStrategy that has received little attention. ...

MicroStrategy has been pressing its case with the IRS, and it could be reasonable to expect the government will bend its way, given the Trump administration’s outward affection for the crypto industry. The IRS is still in the process of drafting rules to implement the new corporate alternative minimum tax.

Robert Willens, a longtime tax analyst who has been tracking MicroStrategy’s IRS issues, said he expects the IRS would decide in MicroStrategy’s favor and exclude unrealized gains on cryptocurrencies under its proposed rules, but he noted there is no guarantee it would do so. “If the Biden group was still in place, they probably wouldn’t get the exemption,” he said. He added that “it would be easy to slot crypto assets into the same exemption that stocks are going to enjoy, because there’s no real difference in the accounting.”

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