Michael Saylor’s latest tax strategy echoes Strategy’s 2022 bitcoin sale

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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. 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. 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". 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. According to the MSTR earnings call, assuming an $80,000 bitcoin price, Strategy has purchased over 434,000 BTC above $80,000 generating a $7.6 billion unrealized loss and a $2.2 billion deferred tax asset at a 29% tax rate. If bitcoin recovers and Strategy sells appreciated bitcoins, that $2.2 billion tax can offsets future gains. The primary goal for the company is to increase "bitcoin per share" which is the ratio of Strategy's total bitcoin holdings divided by its total diluted shares outstanding. The use of proceeds from the bitcoin sale is to retire the $8.2 billion in convertible debt, purchase MSTR common stock when the multiple to net asset value falls below 1.22x or fund $1.5 billion in annual dividend obligations from its perpetual preferred stock Stretch (STRC). MSTR is up 1% in pre-market trading, while bitcoin trades above $81,000. More For You Nearly 600,000 deposits worth $60 million have been collected for a gold T1 phone that has not been delivered to a single confirmed buyer, with terms quietly rewritten in April to remove delivery guarantees. What to know: - Sixteen months after launch, the Trump Mobile T1 phone has collected about $60 million in $100 deposits from roughly 600,000 buyers, but has not delivered a single confirmed device, media reports indicate. - An April update to Trump Mobile’s terms of service states that deposits are only a conditional opportunity to...

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