Strategy Faces Pressure to Break “HODL” Pledge as Bitcoin’s Price Declines

A surprise development for Bitcoin investors is that the investment firm led by Michael Saylor, called Strategy , may soon have to sell some of its significant Bitcoin holdings to meet some lagging debt obligations. This would appear to violate the firm’s “never sell Bitcoin” tenet that has long been a part of Saylor’s investment philosophy. In the firm’s recent 8-K filing with the U.S. Securities and Exchange Commission, it laid out its current state and the challenges it’s facing in the aftermath of Bitcoin’s price decline. Pressure Mounts on Strategy’s Bitcoin Holdings Following the November 2024 elections, when former President Donald Trump emerged victorious, Strategy has been putting the pedal to the metal, if you will, and significantly ramping up its purchases of Bitcoin. In fact, the firm had accumulated 275,965 BTC by the time we reached the moment of the November 2024 election—that total, by the way, was reached at an average price of $93,228 per Bitcoin. With Bitcoin’s recent price plunge, however, the firm is now looking at an unrealized loss on that very same Bitcoin pizza of approximately $4.6 billion. According to the Strategy filing with the SEC (Securities and Exchange Commission), this number is now so large that the firm will likely have to sell some of its Bitcoin if it wants to continue to honor its other debt obligations. At the moment, Strategy possesses an overall sum of 528,185 BTC, holding the majority of it ($392.766 million) in trust for 13 grassy LLCs. The average cost basis for this asset class is $67,458 per Bitcoin. Their total holdings have been calculated to a value of around $40.119 billion. Two89, the strategy’s criminally named technology fund, is responsible for about 1.6% of the 13 grasses holdings, per my calculations. For the record, two grassy leaders—Alvin G. Meyer and David N. Joanovitz—are named as trustees for the two Bitcoin-related LLCs. STRATEGY MAY BE FORCED TO SELL BITCOIN, BREAKING 'HODL' PLEDGE In a recent 8-K filing with the SEC, Strategy may be forced to sell its #Bitcoin to meet debt obligations if $BTC prices continue to decline – potentially breaking Michael Saylor’s @saylor long-standing "never… pic.twitter.com/GfLPMmd2SP — Cult of Blockchain (@BlockchainCult) April 9, 2025 The company’s liquidity difficulty is laid bare in its filing, which explains that without access to favorable debt or equity financing, it might need to liquidate part of its Bitcoin reserve to meet its financial obligations. If it comes to that, it would be a striking about-face from Saylor’s HODL (Hold On for Dear Life) strategy, which emphasizes the belief that Bitcoin is a store of value that should be held long-term and not sold. Many investors view a potential Bitcoin sale by Strategy as something that would shake the very foundations of Bitcoin as an institutionally adoptable asset. A Billion-Dollar Gamble Gone Wrong Strategy’s bet on Bitcoin was not a small one. By buying up such a huge number of Bitcoins, the company placed a gigantic part of its financial assets into the fiery crucible of a very high-risk, very volatile investment. At the time of the purchase, Bitcoin was trading at something that looked suspiciously like a plateau, and Saylor was busy with a kind of a libertarian pep rally, touting the digital asset as the future of finance (and a decent hedge against inflation). Seen from a certain angle, the firm’s commitment to Bitcoin looks like a jab to the chin of traditional finance and a thumbs-up to the much-derided cryptocurrency market. The initial purchase of 275,965 BTC at a cost of $4.4 billion indicates that investing in such a volatile asset carries major risks. As Bitcoin’s price continues to plummet, the firm may find itself needing to divest of a portion of its holdings. But what firm would want to sell a shitload of BTC when it’s promising to not part with its stash? This is a situation that’s now happening for a firm that carried all of these promises and has since seen its market cap reduced by a half in just over 60 days. Potential Impact on the Market Should Strategy liquidate any part of its Bitcoin holdings to meet its obligations, the market will experience significant volatility. A sale of that size could hardly avoid affecting the price. And if the sale had to be done in a fast, forced way, or in some other less-than-ideal condition, it could be really bad for the price and could send a clear signal to other institutional investors that even the most bullish firms on Bitcoin are not immune to the risks of holding the asset in a downturn. The potential sale could undercut the narrative that Bitcoin is a “store of value” that swings with the traditional markets. If a prominent and well-respected firm like Strategy has to sell off a bunch of Bitcoin to cover its debts, that isn’t going to sit well with the other institutional investors Saylor’s firm has made comfortable with the whole Bitcoin space. For individual investors, the news could serve as a blunt reminder of the risks involved in holding Bitcoin, especially for those who have been following the high-profile advice of figures like Saylor. It could also reignite the debates over the sustainability of Bitcoin as an inflation hedge and a safe-haven asset. Looking Ahead: Will Strategy Sell Bitcoin? At present, Strategy has not sold any of its Bitcoin holdings; however, the firm’s 8-K filing has raised some crucial queries about its future intentions. The current phase of Bitcoin’s price slide may compel the firm to make some tough choices about its market posture. Saylor, who has consistently made the case for Bitcoin, may soon find that the company’s debt limits test that case to the breaking point. If the price of Bitcoin stays unstable or keeps moving downward, Strategy may have no alternative but to divest some of its holdings. For the firm to sell even a fraction of its Bitcoin would raise a number of issues, most of which revolve around the risks associated with holding not just the world’s most popular cryptocurrency, but also any cryptocurrency. For enthusiasts or investors who are truly passionate about Bitcoin’s prospects, this moment may well prove to be a pivotal one in the ongoing debate about what seems to be the ever-contentious role of Bitcoin within the financial ecosystem. In the end, this situation highlights just how unpredictable the cryptocurrency market can be and how even the biggest institutional players can find themselves in a tough spot when trying to navigate the market’s built-in volatility. Whether or not the crypto-focused hedge fund has to sell its Bitcoin to meet upcoming margin calls is an open question, but for now, Strategy’s own “HODL” pledge seems to be on the line. Disclosure: This is not trading or investment advice. Always do your research before buying any cryptocurrency or investing in any services. Follow us on Twitter @nulltxnews to stay updated with the latest Crypto, NFT, AI, Cybersecurity, Distributed Computing, and Metaverse news !