Just a few days ago, it looked like investors were starting to lose faith in Strategy (MSTR). Bitcoin (BTCUSD) had plunged below the $60,000 mark, MSTR stock suffered its worst week since late 2022, and headlines focused on something many thought they would never see – Michael Saylor’s company had sold Bitcoin.
To be fair, the sale was small. Strategy unloaded just 32 Bitcoin for $2.5 million to meet preferred stock dividend obligations. But for a company built around Saylor’s famous “buy and hold forever” philosophy, even a slight sale was enough to spark fears that the playbook was changing. Some investors wondered whether Strategy was facing liquidity pressures, while others questioned whether the company’s commitment to Bitcoin was beginning to crack.
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Then came Monday’s surprise.
In a fresh SEC filing, Strategy revealed it had raised $181 million by selling shares and immediately used a portion of the proceeds to buy 1,550 more Bitcoin for approximately $101.3 million. The purchase increased its total holdings to 845,256 coins – acquired for just under $64 billion – reinforcing its position as the world’s largest corporate Bitcoin owner.
The move completely flipped the story. Instead of backing away from Bitcoin, Strategy was doing what it has done for years – using capital markets to accumulate more of the cryptocurrency. Investors quickly took notice, sending MSTR stock sharply higher as concerns faded.
Now, the question is no longer whether Strategy is abandoning its Bitcoin strategy. Instead, investors are once again rewarding the company for doubling down on the very bet that made it famous – buying the dip when others are running for the exits.
About Strategy Stock
Virginia-based Strategy, under the leadership of billionaire Michael Saylor, evolved from a traditional enterprise software provider into the world's largest corporate holder of Bitcoin. Over the past several years, Strategy has used a mix of equity offerings, debt financing, and operating cash flow to aggressively build its Bitcoin treasury, making the cryptocurrency the centerpiece of its corporate strategy. Today, many investors view MSTR less as a software stock and more as a leveraged vehicle for Bitcoin exposure. With a market capitalization of $44.6 billion, Strategy has become one of Wall Street’s most closely watched ways to invest in the long-term Bitcoin story.
Strategy’s shares have been anything but boring. After crushing the broader indexes through much of 2025, MSTR stock eventually ran into turbulence as Bitcoin prices cooled and investor sentiment turned cautious. Since peaking at $457.22 last July, the stock has lost 74.7% of its value, with shares tumbling to a 52-week low of $104.17 in February.
Still, the recent action suggests investors may be warming up again. While MSTR remains down 69.4% over the past 52 weeks, the stock has rebounded 11.3% from its February lows. Monday’s 5.6% rally added to that recovery after Strategy revealed it had resumed buying Bitcoin. For many investors, the latest purchase was a sign that the company’s long-standing Bitcoin playbook remains firmly intact.
www.barchart.com Despite its massive Bitcoin exposure and aggressive growth strategy, MSTR currently trades at a forward non-GAAP price-to-earnings ratio of just 2.46 times, below both the broader sector average and its own historical median. For investors, that suggests the market may still be struggling to fully price in the company’s unique business model.
Strategy is giving income-focused investors another reason to pay attention. The company’s Series A Perpetual Stretch Preferred Stock, Stretch (STRC), carries an annualized dividend rate of 11.50% and pays $0.96 per share every month. Since the start of fiscal 2026, the company has consistently declared and paid, or remains on track to pay, those dividends, reinforcing confidence in the program.
Taking A Closer Strategy’s Q1 Earnings Report
Strategy reported its fiscal 2026 first-quarter results on May 5, and both the top and bottom line missed Wall Street’s projections. The company posted revenue of $124.3 million, up 11.9% year-over-year (YOY), while its GAAP loss per share came in at a staggering -$38.25. But Strategy’s software business actually remained relatively stable.
Meanwhile, gross profit reached $83.4 million, and gross margin held at a healthy 67.1%, showing that the company’s core operations are still generating solid profitability. The real damage came from Bitcoin’s sharp decline during Q1. As Bitcoin prices fell, Strategy was forced to record a massive $14.46 billion unrealized loss on its Bitcoin holdings, contributing to a total operating loss of $14.47 billion. Importantly, those losses were largely paper losses tied to market prices rather than actual Bitcoin sales.
Management made it clear that nothing has changed about the company’s long-term game plan. CFO Andrew Kang reiterated that Strategy remains focused on raising capital, acquiring Bitcoin, holding it for the long run, and increasing Bitcoin per share over time.
A major part of that strategy is Stretch. Executive Chairman Michael Saylor highlighted the product as a key funding vehicle, describing it as a scalable income-focused instrument backed by Bitcoin and cash reserves.
The strategy appears to be gaining traction. In less than a year, Stretch has helped raise $8.5 billion and has grown into the largest publicly traded preferred stock in the world. For Saylor, that success is just the beginning, as he continues building new ways to fund Strategy’s ever-growing Bitcoin treasury.
Meanwhile, analysts monitoring Strategy project the company’s bottom line to rise 866.3% YOY and generate a profit of $116.70 per share in fiscal 2026. But in fiscal 2027, EPS is anticipated to decline 36% annually to $74.73.
What Do Analysts Expect for Strategy Stock?
Wall Street and crypto analysts remain divided on Strategy, but most agree that the company plays an outsized role in the Bitcoin market. Thomas Perfumo, chief economist at Kraken, recently called Strategy the “single most influential entity in the market,” highlighting just how closely investors watch its every move.
That became clear after the company's sale of 32 Bitcoin last week. JPMorgan analysts said the transaction, while small, voluntary, and largely symbolic, still spooked investors and raised questions about whether Strategy would need to rebuild its cash reserves to maintain confidence.
Others are focused on the bigger picture. Grayscale's Zach Pandl noted that Strategy's ability to keep buying Bitcoin depends in part on the continued success of its stock and preferred-share offerings. Still, Bernstein analysts remain upbeat. They argue that Strategy’s dividend commitments are well supported and point out that the company has repeatedly raised more than $1 billion in short periods, suggesting its access to capital remains strong.
Overall, Wall Street appears to be optimistic about MSTR stock, with a consensus “Strong Buy” rating. Of the 18 analysts offering recommendations, 15 are giving it a solid “Strong Buy,” one suggests a “Moderate Buy,” one is playing it safe with a “Hold” rating, and the remaining one advocates a “Strong Sell.”
The average analyst price target of $363.62 indicates impressive 209.7% potential upside from the current price levels. The Street-high price target of $645 suggests that MSTR could rally as much as 449.3% from here.
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www.barchart.com On the date of publication, Sristi Suman Jayaswal did not have (either directly or indirectly) positions in any of the securities mentioned in this article. All information and data in this article is solely for informational purposes. For more information please view the Barchart Disclosure Policy here.
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