Saylor’s Bitcoin Tax Trick: A Tale of Loss and Gain

Disclosure: The author of this story owns shares in Strategy (MSTR).
When the venerable Michael Saylor, that sage of silicon valleys, confirmed on Strategy’s (MSTR) Q1 2026 earnings call that the company was prepared to sell bitcoin, it was as if a thunderclap had echoed through the halls of Wall Street. Yet, this was no new venture-nay, it was a reprise of the 2022 spectacle, where Strategy, ever the clever fox, sold bitcoin to harvest tax losses, only to buy it back with the grace of a dancer on ice.



