MicroStrategy Becomes Most-Shorted U.S. Stock as Bitcoin Paper Loss Hits $7.9 Billion

Software company Strategy, the world’s largest publicly traded corporate holder of Bitcoin, has long been known for an uncompromising buy-and-never-sell strategy. Executive Chairman Michael Saylor’s proposal to sell Bitcoin to fund dividends breaks with that previous pledge and signals a more flexible approach to capital management. The move shows the company confronting the realities of capital markets and has prompted investors worldwide to reassess the viability of crypto-heavy balance sheets.

Strategy reported a first-quarter net loss of $12.54 billion and still holds 818,334 Bitcoin. To raise funds for dividends, the company sold 3,588 Bitcoin for the first time between June 29 and July 6, 2026, generating about $216 million. The move raised market concerns: JPMorgan warned that the policy would add “two-way risk” to crypto markets, while Fortune warned that Strategy could fall into a death spiral.

Strategy, formerly known as MicroStrategy, has pursued a Bitcoin treasury strategy championed by Michael Saylor since 2020, raising funds through share sales and debt issuance to buy the cryptocurrency. The company’s mNAV is calculated by dividing enterprise value by the market value of its Bitcoin holdings. A premium above 1 once supported low-cost fundraising and further purchases, while a reading below 1 could make additional share issuance dilutive and reduce capital-allocation flexibility.

Strategy’s enterprise mNAV fell to about 0.99 on June 26, 2026. With Bitcoin at about $60,000, its 847,363 coins were valued at roughly $51.1 billion, compared with an enterprise value of about $50.4 billion, marking the first such inversion. As of a June 29 report, MSTR’s market capitalization stood at about $29.54 billion after falling more than 45% in 2026, indicating that the market no longer awards the stock its former premium.

Strategy, formerly MicroStrategy, has treated Bitcoin as its primary treasury asset since 2020 and funded further purchases through common-stock and bond issuance as well as STRC perpetual preferred stock. Its Bitcoin holdings are worth about $52 billion, making MSTR a key proxy for corporate Bitcoin exposure and putting its financing and dividend obligations under close scrutiny.

On March 22, Michael Saylor posted a purchase chart on X captioned “The Orange March Continues,” signaling that Strategy would keep buying. The company bought 17,994 Bitcoin on March 9 and another 22,337 on March 16, investing about $2.9 billion during the month. Bitcoin fell as low as $67,725 that day, below Strategy’s average cost of $75,696 and leaving its holdings with an unrealized loss of more than 10%.

Strategy, formerly known as MicroStrategy, has treated bitcoin as a core treasury asset since 2020, funding continued purchases through sales of common and preferred stock. The scale of its holdings has closely tied its share price and financing capacity to bitcoin's performance. A single listed company holding about 4% of the cryptocurrency's total supply has also raised concerns about concentration risk.

Strategy said on July 20, 2026, that it had spent about $101 million to buy 1,550 bitcoin, bringing its total holdings to 845,256, or roughly 4% of bitcoin's maximum supply of 21 million. Despite an unrealized loss of about $10.5 billion, the company plans to continue raising funds through stock sales. Bitcoin's price showed no significant reaction after the announcement.

MicroStrategy, now known as Strategy and trading under the ticker MSTR, holds more bitcoin than any other publicly listed company worldwide. It has long funded its purchases through debt issuance and stock sales. The company had added to its holdings for 13 consecutive weeks since late December last year, making its activity a closely watched indicator of corporate bitcoin demand and MSTR’s share price.

Strategy appeared to make no bitcoin purchases last week and also paused stock sales, potentially ending its 13-week accumulation streak. Executive Chairman Michael Saylor did not issue his customary hint of an impending purchase and instead only reposted information about STRC preferred stock. The company currently holds about 762,099 bitcoin, and the market is watching to see whether buying resumes around its first-quarter earnings report.

MicroStrategy, now known as Strategy, is a leading proponent of corporate Bitcoin reserves, continuously buying the cryptocurrency through debt and equity issuance. The performance of its holdings is seen as a key gauge of whether the digital asset treasury (DAT) model can endure. Earlier weakness in Bitcoin prices had generated paper losses while weighing on the valuations and fundraising capacity of similar companies.

As Bitcoin recovered to about $77,000 in mid-April, Strategy’s shares rose 8% in a single day. Founder Michael Saylor said the company generated $1.3 billion in Bitcoin gains during the first two weeks of April. Strategy currently holds about 780,000 Bitcoin at an average cost of $75,577, putting its position close to break-even and boosting confidence in the DAT market.

MicroStrategy, now known as Strategy, has long used its corporate balance sheet and fundraising proceeds to buy Bitcoin, making it one of the most prominent corporate holders of the cryptocurrency. The accumulation strategy led by founder Michael Saylor has closely tied the company’s share price and financing capacity to Bitcoin’s performance. Its large holdings could also affect market supply and demand and institutional investor sentiment.

In early April, Strategy spent about $1 billion to acquire 13,927 Bitcoin at an average price of roughly $71,900 each, raising its total holdings to 780,897 Bitcoin, or more than 3.7% of the cryptocurrency’s maximum supply of 21 million. The purchase was financed primarily through the issuance of STRC perpetual preferred stock. Saylor said around the same time that Bitcoin may have bottomed near $60,000.

Strategy, formerly known as MicroStrategy, has become the world's largest corporate Bitcoin holder under co-founder Michael Saylor, financing long-term purchases through debt issuance and high-dividend preferred shares. Its financial performance and stock price are therefore closely tied to cryptocurrency markets, while the size of its holdings is large enough to influence market confidence.

Strategy spent about $330 million last week to buy 4,871 Bitcoin at an average price of $67,718 each, lifting its total holdings to 766,970 BTC, or about 3.8% of the circulating supply. The company recorded a first-quarter paper loss of about $14.46 billion and still has about $5 billion in unrealized losses.

Strategy, formerly known as MicroStrategy, has long financed Bitcoin purchases through debt and equity issuance, making MSTR a major Bitcoin proxy in the U.S. stock market. Because its shares are closely correlated with Bitcoin, institutional short positions do not necessarily signal a bearish view of the company and may instead form part of basis trades or paired hedges.

At the time of the relevant reports, short positions in MSTR were equivalent to 14% of the company's market capitalization, the highest proportion among U.S. stocks. Coinbase ranked fourth. Analysts said institutions may hold Bitcoin or BlackRock's spot ETF, IBIT, while shorting MSTR to trade the price spread and manage exposure.