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Michael Saylor Signals Strategy May Sell Bitcoin — Ending Years of Maximalist ‘Never Sell’ Doctrine

by Team Lumida
May 6, 2026
in Crypto
Reading Time: 3 mins read
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Strategy Buys $2.54 Billion in Bitcoin — Its Biggest Purchase Since November 2024
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  • Strategy CEO Phong Le told investors the company would consider selling Bitcoin “to buy US dollars or sell Bitcoin to buy debt if it’s accretive to Bitcoin per share” — the clearest official departure yet from the firm’s longstanding maximalist no-sell stance.
  • Co-founder Michael Saylor outlined a scenario where Strategy could sell Bitcoin to fund preferred stock dividends, likening the model to a real estate developer who buys, appreciates, and then sells assets to service obligations.
  • Saylor also suggested the company may sell Bitcoin at a loss for a tax advantage, citing a $2.2 billion tax credit “lying on the floor” and indicating the firm might sell “just to send the message that we did it.”
  • Strategy holds roughly $67 billion in Bitcoin; S&P Global Ratings assigned the company a junk credit rating last October, warning that convertible debt could mature during a Bitcoin stress period, potentially forcing liquidations at depressed prices.

What Happened?

For years, Strategy’s identity was inseparable from a maximalist Bitcoin accumulation philosophy — Michael Saylor’s consistent message was that there was “no reason to sell the winner.” That stance is now officially softening. On Tuesday’s earnings call, CEO Phong Le said Strategy would not “sit back and just say we’ll never sell the Bitcoin,” citing scenarios where selling Bitcoin to purchase dollars or debt could be accretive to the company’s key metric of Bitcoin per share. Saylor went further, describing a business model where Bitcoin is bought with credit, allowed to appreciate, and then sold to pay dividends — and separately flagging the company’s $2.2 billion tax credit as motivation for a near-term sale, even at a loss, purely to send a market signal.

Why It Matters?

Strategy pioneered the “digital asset treasury” model and its no-sell doctrine was foundational to the entire category. If Strategy is now publicly contemplating Bitcoin sales, it signals that the capital structure of these DAT vehicles has become complex enough that pure accumulation is no longer sustainable on its own terms. The junk credit rating from S&P Global — assigned last October and flagging exactly this risk — appears to have been prescient. Bitcoin’s price recovery to around $81,500 (up 20%+ since the Iran war began) gives Strategy some cushion, but the combination of preferred stock obligations, convertible debt maturities, and a premium-to-NAV that has compressed means the balance sheet requires active management rather than passive HODLing.

What’s Next?

Watch for any actual Bitcoin sale disclosures in coming weeks — Saylor’s comment about selling “just to send the message” suggests a symbolic first sale may be imminent. The more significant question is whether other corporate Bitcoin treasury holders follow Strategy’s lead in treating their holdings as a balance sheet tool rather than a permanent reserve. Any meaningful Strategy sale will be closely watched by crypto markets for the price impact and as a signal about institutional Bitcoin liquidity dynamics.

Source: Bloomberg

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Lumida's website (referred to herein as the "Website") is limited to the dissemination of general information pertaining to its advisory services, together with access to additional investment-related information, publications, and links. Accordingly, the publication of the Website on the Internet should not be construed by any client and/or prospective client Lumida’s solicitation to effect, or attempt to effect transactions in securities, or the rendering of personalized investment advice for compensation, over the Internet.

Any subsequent, direct communication by Lumida with a prospective client will be conducted by a representative that is either registered or qualifies for an exemption or exclusion from registration in the state where the prospective client resides.

‍Lead Capture Forms: By submitting your contact information in the forms on this site, you are not obligated to invest in Lumida's product or services.
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