Bitcoin’s rally past the $110,000 mark sparked a fresh round of buying from Strategy, the corporate Bitcoin giant helmed by Michael Saylor. But even as the company doubled down on crypto, its stock tumbled in the face of legal trouble and insider sales.

Strategy revealed a new purchase of 4,020 Bitcoin between May 19 and 23, totaling $427.1 million. The average price per coin was $106,237, placing the buy just ahead of Bitcoin’s all-time high of over $110,000 on May 22. The move continues Saylor’s long-standing approach of accumulating Bitcoin regardless of market peaks.

Fourth Purchase in May

The latest buy brings Strategy’s total holdings to 580,250 BTC, worth over $63 billion at current prices. The firm has spent around $40.61 billion on its Bitcoin stash, averaging $69,979 per coin.

Source: Strategy

This marks the company’s fourth BTC acquisition in May alone, reaffirming Saylor’s commitment to long-term accumulation. In late 2024, Saylor declared he would keep buying Bitcoin at the top “forever,” a stance the company appears to maintain despite price volatility and growing regulatory scrutiny.

Alongside the Bitcoin purchases, filings show multiple share sales by Strategy executives. Director Jarrod Patten sold 2,650 MSTR shares between May 16 and 21, worth nearly $1.1 million. Since late April, Patten has offloaded 17,050 shares, netting around $6.7 million.

Chief financial officer Andrew Kang also sold 2,185 shares on May 23, valued at $719,447, according to a separate filing. The insider transactions coincided with Strategy’s large Bitcoin purchases, potentially signaling diverging views within the company.

Bitcoin Price Prediction

Bitcoin is no longer just a speculative asset dominated by retail investors. As corporate treasuries increasingly incorporate BTC into their long-term strategies, the market is undergoing a fundamental shift.

Tracy Jin, COO of MEXC, highlighted to financemagnates.com how institutional momentum is reshaping Bitcoin’s trajectory and what that means for the broader crypto ecosystem in the second quarter.

Jin forecasts that if institutional and corporate momentum continues, Bitcoin could soon break through resistance levels around $109,500 to $112,000 and aim for $140,000 by late summer.

However, if macroeconomic pressures dampen corporate demand, BTC could test support near $106,000 to $107,000, with a deeper drop toward $94,000 if those levels fail.

Stock Drops 6% After Class-Action Lawsuit

Despite Bitcoin’s gains, Strategy’s stock hasn’t followed suit, currently down 6% in the past week. The stock hit a record close of around $474 on November 19, 2024, but investor sentiment has soured following a lawsuit filed on May 19.

The class-action suit alleges the company misled shareholders about its Bitcoin investment strategy. The complaint seeks damages for those impacted by what it claims was securities fraud in April 2025.

The legal battle adds a layer of risk for shareholders even as Bitcoin continues to rally. Saylor’s Strategy remains one of the most aggressive institutional Bitcoin buyers. While its crypto holdings swell in value, the firm now faces the dual pressure of shareholder litigation and a falling stock price.