At the forefront of financial news, Strategy, formerly known as Microstrategy, is once again capturing headlines. The company, renowned for its substantial Bitcoin investments, is undergoing significant board changes. This week, a notable shift occurred as insiders moved to capitalize on stock gains, a move that has intrigued market watchers.

According to insights from Protos, Strategy insiders have been strategically capitalizing on their stock holdings. A significant move was made by Carl Rickertsen, who liquidated his entire stake, netting over $10 million. His initial purchase in October 2022, when shares were valued at under $25, has paid off significantly, with the stock appreciating roughly 16 times in less than three years.

Protos reports that 2025 has seen no insider purchases, while 26 insider sales have been recorded, amounting to $864 million more in sales than buys. This trend is raising eyebrows among retail investors, particularly as the stock has seen a 10% decline recently.

Despite Strategy’s aggressive acquisition of Bitcoin, the company’s stock hasn’t mirrored this growth. Currently holding approximately 582,000 BTC, valued at about $63 billion, the firm’s stock has nonetheless dipped by 10% over the past month. In contrast, Metaplanet, a smaller player in the Bitcoin market, has seen its stock soar by 150% during the same period, prompting questions about Strategy’s stock performance.

Renowned Bitcoin skeptic Peter Schiff, a long-time critic, recently expressed skepticism about Strategy’s business model. Schiff labeled it a “complete fraud” and predicted impending bankruptcy. He voiced these opinions following a Bloomberg report on the company’s Bitcoin reserves, reiterating his preference for gold over Bitcoin, albeit admitting past regret for not investing in Bitcoin earlier.

Supporters of Strategy’s Bitcoin-centric approach argue that the volatility is a natural aspect of its strategy and that the long-term benefits will outweigh the risks. However, the wave of insider sales continues to be a cause for concern among investors.

As the market closely observes Strategy’s actions, key points of interest include potential insider buybacks, the response of share prices to new Bitcoin acquisitions, and whether critics like Schiff can influence broader market sentiment. Although Strategy’s trajectory remains bold and ambitious, the recent insider sales have undoubtedly placed the company under heightened scrutiny.