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Home News Crypto

Saylor’s Best Move Now May Be to Stop Buying Bitcoin

by Team Lumida
June 24, 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’s STRC preferred shares hit a record 17.5% discount to their $100 par value last week and remain at an ~13% discount, while common stock MSTR fell to its lowest since May 2024 — both reflecting deep investor concern about the company’s funding model.
  • CryptoQuant’s head of research argues Strategy should pause Bitcoin purchases and rebuild its cash buffer to ~$2.8 billion (24 months of dividend coverage), down from $1.4 billion currently after falling 36% since the start of 2026.
  • Strategy is paying an 11.5% annual yield on STRC (effective yield ~13.17% at current discounted prices), and the company is funding Bitcoin purchases primarily through common equity sales — not the preferred shares it had pledged to prioritize.
  • At the start of June, Strategy disclosed it had sold 32 Bitcoin — its first sale since 2022 — a symbolically significant crack in Saylor’s “never sell” narrative, even if the quantity was negligible versus $57B in total holdings.

What Happened?

Strategy Inc. — Michael Saylor’s Bitcoin-accumulation vehicle — is under sustained financial pressure after months of Bitcoin price weakness. The company sits at a notional $11 billion loss on its total Bitcoin holdings. Its STRC preferred shares, which carry an 11.5% annual yield reset monthly, fell to a record 17.5% discount to their $100 par value last week, and remain at an ~13% discount. MSTR common stock has hit multi-year lows. Meanwhile, Strategy’s dollar cash buffer has fallen 36% this year to just $1.4 billion — partly due to a May repurchase of $1.5 billion in 0% convertible notes — leaving limited cushion to support STRC dividends. Between June 15-21, Strategy bought $34.9 million of Bitcoin funded entirely through common stock sales, not the preferred share issuances it had pledged to prioritize.

Why It Matters?

Strategy’s model depends on a virtuous flywheel: raise capital at low cost, buy Bitcoin, Bitcoin appreciates faster than obligations compound, repeat. That flywheel is now running in reverse. The STRC discount reflects market skepticism about whether Strategy can sustainably pay the 11.5% dividend if Bitcoin stays depressed. The June 32-Bitcoin sale — negligible in dollar terms, enormous in narrative terms — cracked the “never sell” commitment that underpinned investor confidence. More structurally: as spot Bitcoin ETFs see outflows ($2.4B in June alone) and speculative interest fades, Strategy has become the marginal buyer of last resort for Bitcoin. If Strategy slows or stops buying, it removes a key source of demand support for the asset it holds almost exclusively.

What’s Next?

According to CryptoQuant’s Julio Moreno, the path back to STRC trading at par requires rebuilding the cash reserve to ~$2.8 billion — providing 24 months of dividend coverage. That means pausing Bitcoin purchases and potentially issuing equity to shore up liquidity rather than deploy it into more crypto. Strategy is not technically required to sell Bitcoin to support STRC; it can raise the dividend yield or issue equity to signal capacity to pay — tools already in use. But those are delay tactics, not solutions, if the underlying Bitcoin price trend doesn’t reverse. The company’s viability as currently structured hinges on Bitcoin appreciating meaningfully from current levels before its obligations compound further.

Source: Bloomberg

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© 2025 Lumida Wealth Management LLC is an SEC registered investment adviser. Privacy Policy. Cookies Policy.
Disclaimer Important Information This site is for informational purposes only. Information presented on this site does not constitute as investment advice.

Lumida Wealth Management LLC (‘Lumida”) is an SEC registered investment adviser. SEC registration does not constitute an endorsement of the firm by the Commission nor does it indicate that the adviser has attained a particular level of skill or ability.

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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