MicroStrategy Eyes New Bitcoin Milestone With Another Purchase

Strategy Inc. (formerly MicroStrategy) has signaled it is preparing to execute a Bitcoin acquisition that would eclipse the massive $1.25 billion purchase completed just last week.

On January 18, Michael Saylor posted a graphic to the social media platform X captioned “Bigger Orange.” Market analysts widely interpreted the phrase as a signal of intent to surpass the 13,627 Bitcoin the firm recently acquired.

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Strategy Signals Record Bitcoin Purchase Amid Falling Stock Premium

That previous tranche had already solidified the company’s position as the largest corporate holder of the asset.

However, a purchase exceeding that volume would push Strategy’s total holdings above the 700,000 Bitcoin threshold.

This milestone would place the firm’s treasury in rare air, trailing only BlackRock’s IBIT exchange-traded fund and the 1.2 million BTC estimated holdings of Satoshi Nakamoto, the network’s pseudonymous founder.

The aggressive move comes at a precarious moment for the enterprise software firm.

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Strategy’s stock plummeted more than 50% last year, and its critical market-to-net-asset-value (mNAV) premium has collapsed to approximately 1.0x.

This premium compression threatens the arbitrage model Saylor has historically utilized to fund acquisitions.

With institutional capital increasingly flowing toward spot Bitcoin ETFs—which offer exposure without the complexity or premiums associated with Strategy shares—the firm has lost the easy leverage it once enjoyed.

To sustain its accumulation pace against this backdrop, Strategy has pivoted to aggressive funding tactics.

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In the past year alone, the company raised $25 billion through the sale of common stock and the issuance of new types of preferred shares, including STRC.

Meanwhile, Wall Street has reacted to this dilution with caution. TD Cowen recently downgraded its price target for the stock to $440 from $500 while maintaining a Buy rating.

The firm cited a decline in “Bitcoin Yield” for fiscal 2026, a proprietary metric measuring Bitcoin exposure per share. Analysts noted that the company’s reliance on issuing greater equity to fund purchases is actively diluting this yield for shareholders.

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Despite the skepticism, some market observers argue that Strategy has engineered a structural moat that traditional finance cannot easily bridge.

Makin suggested that the mounting regulatory and market pushback facing the firm is a reaction to the model’s efficacy rather than its flaws.