Michael Saylor’s Strategy Adds $765M in Bitcoin

Strategy, the business intelligence firm renowned for its relentless Bitcoin accumulation, has just made another massive investment — snapping up $765 million worth of BTC in its latest buy.

The announcement reinforces the company’s position as the most aggressive corporate holder of the digital asset, even as pressure mounts on multiple fronts.

Despite the bold purchase, Strategy is now facing growing skepticism from the market — and from seasoned critics. Notably, renowned short-seller Jim Chanos, known for his early warnings on Enron, has reportedly taken a bearish position against the firm. In a curious twist, he’s also hedged his bet by buying Bitcoin itself, suggesting that his doubts lie more with Strategy’s execution than with the cryptocurrency it champions.

Meanwhile, Strategy co-founder Michael Saylor has responded to the criticism in typical fashion — publicly and with confidence. Over the weekend, he fired back at short-sellers via social media, playfully referencing an old investing proverb with a Bitcoin twist: “Never short a man who buys orange ink by the barrel.”

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But not all the heat is coming from investors. According to a recent regulatory disclosure, Strategy is now entangled in a class-action lawsuit. The complaint alleges that the company misled shareholders by downplaying the inherent risks of its Bitcoin-centric financial strategy. Following the news, shares of Strategy slipped 2% in pre-market trading.

While the firm continues to double down on its BTC thesis, its legal and reputational challenges are growing just as fast. Whether the latest acquisition signals confidence — or overreach — may ultimately depend on how the market digests both the buy and the backlash.

Alexander Stefanov