Strategy CEO sells company shares
Strategy CEO’s stock gifting raises concerns among investors
The recent disclosure that Strategy President and CEO Phong Le gifted 8,400 MSTR shares over the past three months has raised significant concerns within the crypto and investor communities.
Edward Farina, head of XRP Healthcare, called attention to the transaction using the SEC’s Form 4, labeling the move as potentially “shady” and suggesting it could be a bearish signal for Bitcoin, given Strategy’s status as the largest corporate Bitcoin holder, reports CoinGape.
Although the transaction was coded as a gift, implying zero-dollar compensation, Farina pointed out that this action follows other notable insider sales by Strategy leadership, including director Carl Rickertsen, who reportedly sold nearly $10 million worth of stock in 2025. The timing of these moves coincides with Strategy’s ongoing struggle to push MSTR stock decisively above the $400 resistance level, with shares currently trading around $383.
Questions Linger Over Leadership Confidence
While gifting shares is not uncommon in corporate circles, the broader context has triggered speculation about leadership’s confidence in Strategy’s long-term trajectory. Farina emphasized that Phong Le had also sold over $3 million in MSTR shares recently, adding to the narrative that insiders might be cashing out amid the stock’s substantial rally of nearly 200% over the past year.
Despite this, Le retains a considerable stake in the company, holding over 16,000 common shares and 10,500 preferred shares, which somewhat tempers fears of a complete leadership exodus. However, the optics of gifting large amounts of shares combined with prior sales from top executives raise concerns about internal sentiment, especially as Strategy’s stock faces repeated rejection at key technical levels.
Bitcoin Movements Signal Strategy Adjustments
Simultaneously, Strategy has been making significant moves within its Bitcoin wallets, transferring 7,383 BTC—worth nearly $796 million—to three new addresses, according to blockchain analytics from Arkham Intelligence. These transfers are widely interpreted as part of a custodial strategy overhaul rather than a liquidation plan, as the company has consistently adhered to its Bitcoin accumulation narrative, with only one notable sale in December 2022.
Strategy’s co-founder and Bitcoin advocate Michael Saylor continues to champion the firm’s aggressive Bitcoin purchasing strategy, recently hinting at further acquisitions. While the leadership’s stock transactions raise some eyebrows, Saylor’s unwavering Bitcoin commitment seems to reinforce the company’s core bullish stance on the digital asset. The contrast between the stock sales and Bitcoin wallet activity leaves investors grappling with mixed signals about the company’s immediate and long-term intentions.
Recently we wrote that Michael Saylor, the Executive Chairman of Strategy, presented an in-depth analysis of Bitcoin's theoretical and practical applications at BTC Prague.
