Grayscale floats $3B+ Bitcoin sale as Strategy faces rising cash and preferred dividend pressure

Grayscale's head of research, Zach Pandl, said Strategy could bolster market confidence by selling more than $3 billion worth of Bitcoin to meet most of its cash obligations over the next two years, as investor scrutiny intensifies around the firm's balance sheet and preferred-share structure. Pandl said he expects Strategy to lift the dividend rate on STRC by 50 basis points. He added that doing so would increase obligations by roughly $100 million over two years and "probably does not help market confidence." His comments came as STRC traded well below its $100 par value and Bitcoin probed the $59,000–$60,000 support area. Pandl argued a Bitcoin sale exceeding $3 billion could cover nearly all cash obligations due in the next two years, and may prove more effective than boosting STRC's dividend while the preferred continues to trade at a discount. Strategy's annual preferred dividend obligations are about $1.2 billion, largely tied to STRC and other preferred instruments. STRC is structured to trade near its $100 reference price, but it fell to as low as $71.25 on Friday, about 29% below par. In its latest 8-K filing, Strategy said it increased its U.S. dollar reserve by $300 million to $1.4 billion. CryptoQuant estimated that reserve provides about 14 months of dividend coverage, down from a cushion that once exceeded seven years. CryptoQuant also urged Strategy to pause Bitcoin purchases and rebuild cash, noting cash reserves have fallen 38% in 2026 and that investors are paying closer attention to the company's capital structure. Galaxy Digital CEO Mike Novogratz linked Bitcoin's recent slide to what he described as "a MicroStrategyled breakdown in confidence around that complex," adding that it is contributing to a broader confidence issue for Bitcoin. He also cited hawkish U.S. monetary policy and softer crypto sentiment. Novogratz said Strategy's sale of 32 BTC dented the longstanding belief the firm would never sell. The sale occurred between May 26 and May 31 at an average price of about $77,135 per BTC. While small relative to total holdings, it marked Strategy's first Bitcoin sale since December 2022. Strategy holds 847,363 BTC, according to a StrategyTracker chart shared by Michael Saylor. The chart valued the position at $50.88 billion as of June 28, 2026, and showed an average cost of $75,653 per BTC across 113 purchase events. Novogratz warned that a decisive break below the $59,000–$60,000 zone could open a move toward $45,000. That remains a market forecast rather than a confirmed outcome and depends on whether selling pressure persists. Against that backdrop, Strategy's enterprise multiple to net asset value (mNAV) has fallen below 1.0 for the first time, implying the equity market is valuing the company at less than the spot value of the Bitcoin on its balance sheet. The shift matters because Strategy's model has relied on issuing equity or preferred shares at favorable levels to fund additional Bitcoin purchases. When MSTR and STRC trade weakly, those financing channels become harder to use without diluting shareholders or adding obligations. MSTR closed Friday at $82.31, down 26.86% for the week. The stock is also off more than 45% year to date, while Bitcoin has traded near 20-month lows around $59,000. Strategy still bought 520 BTC for $34.9 million between June 15 and June 21. Saylor posted "We're gonna need more charts," alongside the StrategyTracker data, signaling continued emphasis on the company's Bitcoin treasury strategy. CryptoQuant said Strategy is not required to sell Bitcoin to support STRC, pointing to alternatives such as raising the current 11.5% dividend yield. Pandl countered that a higher dividend may fail to restore confidence if investors remain focused on cash coverage and preferred obligations. Bitcoin advocate Samson Mow said STRC has a "self-repairing mechanism" because Strategy halts new at-the-market issuance when the stock trades below $100, while the lower price increases the effective yield for new buyers. He said that dynamic could attract demand and gradually move STRC closer to par. Ripple CEO Brad Garlinghouse also criticized Strategy's Bitcoin financing approach last week. He said he remains bullish on Bitcoin but argued that Saylor's preferred-stock model has weighed on the broader crypto market as STRC fell to record lows.