MSTR Stock Faces Headwinds as MSCI Index Reclassification Looms

As the cryptocurrency market watches closely, Michael Saylor’s Strategy is bracing for a pivotal moment. On January 15, MSCI will determine whether digital asset treasury companies qualify as investment funds—a decision that could reshape the investment landscape for MSTR shareholders.

The MSCI Index Decision: What’s At Stake

The stakes are extraordinarily high. JPMorgan has calculated that a delisting from MSCI’s global indices could trigger approximately $2.8 billion in outflows from Strategy. Market participants are pricing in this risk heavily, with Polymarket data showing a 77% probability of delisting by March 31.

This isn’t merely a technical reclassification. For a stock already reeling from recent losses, index removal would represent another significant headwind. The consultation period on excluding digital asset treasury companies wrapped up recently, setting the stage for what could be a watershed moment for MSTR investors.

Deteriorating Stock Performance and Expert Skepticism

The MSTR narrative has shifted considerably. The stock shed 50% from its 2025 peak above $400, with particular weakness emerging in the second half of the year as Bitcoin retreated below $100,000. This decline raises fundamental questions about whether the strategy of treasury-backed equities genuinely creates shareholder value.

Peter Schiff, a prominent market observer, has amplified these concerns. Schiff’s latest commentary questions whether the current corporate approach remains viable, pointing to the company’s dividend policy as evidence of underlying stress. Strategy recently increased its preferred stock dividend to 11% monthly—a move Schiff characterizes as unsustainable given the company struggled to maintain the initial 10% payment level.

2026 Outlook: Analyst Caution Prevails

Looking ahead to 2026, skeptics anticipate greater pressure on MSTR valuations. Schiff projects that if Bitcoin experiences a more pronounced correction than occurred in 2025, the equity could face even steeper declines. He also notes that if Strategy had been included in the S&P 500, it would have ranked among the index’s worst performers.

The fundamental criticism runs deeper: some analysts argue that the company’s pivot toward Bitcoin acquisition has diluted rather than enhanced shareholder returns compared to traditional corporate strategies.

As investors await the January 15 determination, MSTR shareholders must weigh whether index membership retention will stabilize valuations or whether structural headwinds will continue to dominate price action in the year ahead.