Grayscale Says Strategy May Need $3 Billion Bitcoin Sale to Restore Confidence

Highlights:

• Grayscale Head of Research says Strategy may need a major Bitcoin sale to rebuild confidence.
• Pandl warns that a small STRC dividend increase may not be enough to calm investor concerns.
• Strategy’s funding model faces pressure as STRC trades far below its stated value.

Grayscale Head of Research Zach Pandl has raised fresh concerns about Strategy’s capital structure as pressure grows around the company’s STRC preferred stock and Bitcoin-backed funding model. In a June 27 post on X, Pandl said Strategy may increase the STRC dividend next week, but he argued that a larger Bitcoin sale could do more to restore market confidence.

Pandl said his expected outcome is a 50-basis-point increase in the STRC dividend. According to him, that move would add about $100 million in dividend obligations over the next two years and would “probably” not help market confidence. However, he said his preferred outcome would be for Strategy to sell at least about $3 billion in Bitcoin to cover nearly all cash obligations for the next two years, excluding one convertible note.

For Strategy $MSTR next week

*what I think happens: increase in $STRC dividend of 50bp, which equates to ~$100mn higher dividend obligation for next 2yrs; probably does not help market confidence

*what I hope happens: sale of ≥ ~$3bn $BTC to cover nearly all cash obligations… https://t.co/8KyZpIBxFL

— Zach Pandl (@LowBeta) June 27, 2026

Laura Shin also raised concerns about the pressure building around Strategy. In a June 26 post, she said the issue is not Bitcoin itself, but “one man’s leveraged, unaccountable bet on it.” She noted that STRC had fallen below par, Strategy’s capital structure was under pressure, and MSTR had dropped to a two-year low.

Strategy’s STRC Pressure Becomes a Bigger Concern

STRC, also known as Stretch, is Strategy’s variable-rate perpetual preferred stock. It is designed to pay cash dividends and trade close to a $100 stated amount. Strategy says STRC’s dividend rate can change every month to help the stock trade closer to its $100 stated value. For June, the company listed the annualized dividend rate at 11.50%.

However, STRC has recently traded far below its stated value. The current price shown for Strategy STRC is $74.57. That has raised concerns because Strategy has used preferred stock and common stock sales to support its Bitcoin accumulation strategy. When STRC trades near $100, it works better as a funding tool. When it trades much lower, investors may demand a higher return, and Strategy’s future financing can become more expensive.

Recent market reports show that STRC’s effective yield has climbed sharply as its price dropped. That reflects weaker investor confidence in the preferred stock. It also shows why Pandl believes a small dividend increase may not be enough to calm the market.

Bitcoin Sale Debate Grows Around Strategy

Strategy has already shown that it is willing to sell a small amount of Bitcoin to meet cash needs. Strategy sold 32 BTC for about $2.5 million between May 26 and May 31. The company said proceeds from the sale were expected to fund distributions on preferred stock.

That sale was small compared with Strategy’s total Bitcoin holdings, but it still attracted attention because the company is widely known for its long-term Bitcoin accumulation strategy. Strategy remained the largest corporate holder of Bitcoin, with more than 847,300 BTC.

Pandl’s point differs from a typical bearish call. He is not saying Strategy lacks Bitcoin. Instead, he is focusing on cash flow. Bitcoin does not generate income on its own, whereas preferred stock dividends require cash payments. That creates pressure when Strategy’s stock and preferred shares weaken.

CryptoQuant gave a more cautious view. In a recent report, the firm said that Strategy is not forced to sell Bitcoin to support STRC. Instead, it said the company should pause new Bitcoin purchases and rebuild its cash reserve. CryptoQuant said Strategy’s dividend obligations have grown sharply, while its cash cushion has weakened. That makes liquidity more important now, even though Strategy still holds a very large Bitcoin position.

Strategy’s annualized dividend obligations have nearly quadrupled to $1.2B, while its cash reserve has fallen 38% in 2026.

Dividend coverage collapsed from 7+ years to just 14 months.

The company needs to stop buying Bitcoin and rebuild cash. pic.twitter.com/TR0oaAnT5k

— CryptoQuant.com (@cryptoquant_com) June 23, 2026