Strategy, Michael Saylor’s bitcoin investment firm, shifted approximately 411 Bitcoin valued at over $30 million into Coinbase Prime, raising alarms across the crypto community about a possible upcoming sell-off. The firm’s leadership has previously indicated that they might liquidate parts of their holdings depending on market conditions and shareholder interests.
The speculation intensified after Strategy’s CEO, Phong Le, suggested in a recent interview that short-term sales to optimize tax positions could be on the horizon. The firm posted a significant net loss in the first quarter, largely due to BTC’s recent price drop, creating opportunities for tax loss harvesting. Market predictions currently assign a high probability to Strategy selling Bitcoin within the year.
Additional concerns stem from Strategy’s recent retirement of $1.5 billion in convertible debt due in 2029. This move depleted the firm’s USD reserves earmarked to cover preferred stock interest, reducing coverage from a 2.5-year buffer to just six months, according to analyst Glenn Cameron. Such a reduction raises risks if market conditions or stock sale ("ATM") windows tighten unexpectedly.
Investment experts like Jeff Dorman, Chief Investment Officer at Arca, warned that Strategy's handling of convertible debt and Bitcoin assets creates financial pressure, suggesting that losses among stakeholders could materialize within months. Meanwhile, Bitcoin’s price extended its pullback toward the lower boundary of its 2026 ascending channel, wiping out most second-quarter gains but showing some resilience at critical support levels.