Michael Saylor’s latest tax strategy echoes Strategy’s 2022 bitcoin sale
Key takeaways
- In December 2022, Strategy sold bitcoin for tax-loss harvesting purposes — the same rationale the company now appears to be signaling to the market once again.
- On Dec. 22, 2022, Strategy sold 704 bitcoin for approximately $11.8 million at $16,776 per coin, but immediately repurchased 810 bitcoin two days later.
- Bitcoin fell 23% in Q1 2026, from $87,500 to $67,700.
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.Disclosure: The author of this story owns shares in Strategy (MSTR).When executive chairman Michael Saylor confirmed on Strategy’s (MSTR) Q1 2026 earnings call on May 6 that the company was prepared to sell bitcoin, it appeared to mark a shift for the world’s largest publicly traded corporate holder of the cryptocurrency. But the move would not be unprecedented. In December 2022, Strategy sold bitcoin for tax-loss harvesting purposes — the same rationale the company now appears to be signaling to the market once again.
On Dec. 22, 2022, Strategy sold 704 bitcoin for approximately $11.8 million at $16,776 per coin, but immediately repurchased 810 bitcoin two days later. The sale was designed to carry back capital losses against previous gains and generate a tax benefit. A tax loss harvesting event.
"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".