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Michael Saylor’s latest tax strategy echoes Strategy’s 2022 bitcoin sale
Michael Saylor confirmed the company was prepared to sell bitcoin, reviving a tax loss harvesting strategy first used in 2022.
May 11, 2026, 10:57 a.m. 2 min read
What to know:
- Strategy previously sold 704 BTC in December 2022 to realize tax losses before quickly rebuying 810 bitcoin, two days later, a move designed to offset prior capital gains and secure tax benefits.
- With bitcoin down 23% in Q1 2026, Strategy recorded a $12.54 billion unrealized loss and built a $2.2 billion deferred tax asset that could offset future gains.
“MicroStrategy plans to carry back the capital losses resulting from this transaction against previous capital gains, to the extent such carrybacks are available under the federal income tax laws currently in effect, which may generate a tax benefit”.
Bitcoin fell 23% in Q1 2026, from $87,500 to $67,700. Under FASB fair value accounting rules adopted Jan 1, 2025, Strategy marks its entire bitcoin holdings to market every quarter, in Q1 posted a $12.54 billion loss which pushed unrealized losses directly through the income statement and generating a $2.2 billion deferred tax asset across its higher cost basis holdings.
