Grayscale's Bold Proposal: How Selling $3B in Bitcoin Could Save Strategy From Its $14B Unrealized Loss

Strategy, the Bitcoin-focused corporate treasury firm formerly known as MicroStrategy, has been under intense scrutiny from the broader crypto and investment community. Now, Zach Pandl, Head of Research at Grayscale, has entered the conversation with a pointed financial assessment that could reshape how the company handles its growing obligations.

In a recent post on X, Pandl outlined a critical financial crossroads facing Strategy in the coming weeks. His analysis centers on two possible paths the company could take to attract fresh capital and maintain investor confidence.

The first option involves raising the dividend on Strategy's STRC preferred shares by 50 basis points. While this move could draw in new investors seeking higher yields, Pandl warns it would simultaneously increase the company's fixed financial commitments. Over the next two years, this approach could pile on approximately $100 million in additional dividend obligations — a burden that might further erode, rather than restore, investor trust.

The second and more provocative option, which Pandl appears to favor, involves the sale of at least $3 billion worth of Bitcoin. According to his assessment, liquidating this portion of BTC holdings would cover nearly all of Strategy's cash obligations for the next two years, excluding one of its convertible notes. More importantly, such a move would likely restore market confidence by demonstrating the company's ability to meet short-term financial commitments without relying on external financing.

While a $3 billion BTC sale would reduce Strategy's overall Bitcoin reserves, it would significantly improve the firm's liquidity profile and lower refinancing risk — two factors that weigh heavily on institutional investors evaluating MSTR stock.

As of the time of writing, Strategy holds a staggering 847,363 Bitcoin, valued at approximately $50.9 billion. Since August 11, 2020, the company has made 113 separate Bitcoin purchases and only one sale, with an average acquisition cost of $75,646 per coin.

However, the market has not been kind to Strategy lately. MSTR shares fell below the $100 mark for the first time since March 2024, with the stock trading at $82.31 following a 3.54% single-day decline. STRC preferred shares were changing hands at $74.87. Meanwhile, Bitcoin itself was trading at $60,086 — down more than 18% over the previous month — amplifying the pressure on Strategy's balance sheet.

Perhaps most alarming is the scale of Strategy's unrealized losses. The company is currently sitting on an estimated $14 billion in unrealized losses, while its 11.5% dividend commitment translates to approximately $1.2 billion in annual payouts — a figure that demands robust cash flow management.

Data from CryptoQuant adds another layer of concern. The MicroStrategy Price-to-BTC Reserve Ratio chart shows that by June 2026, both the ratio and MSTR's share price had dropped sharply compared to the premium levels seen in 2024 and 2025. Investors who once paid a significant premium to gain exposure to Strategy's Bitcoin treasury are now doing so at a far lower markup — a clear signal of diminishing enthusiasm.

The simultaneous decline in both the stock price and the valuation ratio points to waning institutional confidence in Strategy's long-term treasury model. Whether the company chooses to increase dividends or liquidate a portion of its Bitcoin holdings, either decision carries substantial consequences for its financial standing and investor relations moving forward.