• MSCI (MSCI)’s index-eligibility decision on Strategy (MSTR) is due by October 16, a binary event that could cut off passive fund flows.
  • Executive Chairman Michael Saylor told Bloomberg he expects Bitcoin to reclaim $100,000, citing regulatory tailwinds and tokenization.
  • Strategy bought 250 BTC for $21.5 million last week while repurchasing $192.4 million of its STRC preferred shares, a sign capital-structure management is taking priority.

A Two-Track Story

Michael Saylor, the executive chairman of Strategy, took the stage at a Bloomberg event on Tuesday with a familiar message: Bitcoin’s bear market is over. In an interview, he predicted BTC would climb back above $100,000 this cycle, with annual growth of 20% to 30% over the next two decades. Bitcoin was trading near $83,000 at the time, roughly 20% below that target and well off its October 2025 peak of about $126,000, according to recent reporting.

Saylor’s optimism is not new. What is new is the scale of the near-term risk facing his company that has little to do with Bitcoin’s price. MSCI is expected to announce as soon as October 16 whether it will adopt broader rules that would exclude so-called non-operating companies from its indexes. Strategy, the largest corporate holder of Bitcoin, is squarely in the crosshairs. The proposal would first test whether an issuer has substantial operating assets, then apply five financial-ratio screens. Failing four of the five could trigger ineligibility.

Why the Index Decision Matters More Than the Forecast

Index inclusion is a quiet but powerful force in equity markets. If MSCI determines that Strategy no longer qualifies as an operating company, passive funds tracking its benchmarks would be forced to sell. The company’s shares moved about 6% higher in after-hours trading in January when MSCI declined to implement a narrower exclusion targeting digital-asset treasury companies – a sign of how sensitive investors are to benchmark eligibility. Strategy has pushed back, arguing in a response letter that it runs substantive software and Bitcoin operating businesses, not an investment fund. “What institutional investors like us are really focused on is regulatory stability,” Saylor said at the conference, also downplaying the potential index exclusion as minor. That is management’s assessment, not a settled fact. MSCI’s stated concern is that treasury companies resemble investment vehicles its operating-company benchmarks are designed to avoid.

Capital Allocation Shifts

The MSCI fight is unfolding as Strategy’s weekly disclosures reveal a subtle shift in priorities. In the week ending October 11, the company bought 250 BTC for $21.5 million – down from $28.7 million the prior week – bringing its holdings to 848,250 BTC, acquired for $64 billion at an average cost of $75,444 per coin. Over the same period, it repurchased $192.4 million of its STRC preferred shares. That is nearly nine times the amount spent on Bitcoin. The message: managing the capital structure and supporting preferred dividends have become as important as accumulating more coins.

Strategy still holds $4.88 billion in a dollar reserve earmarked for preferred dividends and debt interest, plus $640.5 million in cash. But the company’s second-quarter results showed an $8.22 billion net loss, driven almost entirely by Bitcoin valuation changes. A preliminary third-quarter disclosure estimated a $20.91 billion gain on digital assets, yet that accounting swing does not generate cash. The full earnings release is set for October 29.

Financing the Machine

To fund its Bitcoin purchases, Strategy has relied on issuing common stock, preferred securities and other instruments. In the latest week, it sold 125,183 common shares for $21 million and used those proceeds, plus $500,000 in cash, to buy BTC. That reliance on capital markets means any adverse index decision could ripple directly into the company’s ability to finance future accumulation. Passive investors, who might otherwise hold the stock without a view on Bitcoin, could be forced to exit.

Saylor’s bull case rests on wider banking adoption, friendlier U.S. regulation and growth in tokenized securities. He has also pointed to stalled federal legislation that removed potentially restrictive provisions. Those are his interpretations, not resolved facts. The company recently announced an AI-transformation event series with Google Cloud (GOOGL), part of an effort to highlight its software business.

Investors will get two clear checkpoints in the coming weeks: MSCI’s decision by October 16 and Strategy’s full third-quarter earnings on October 29. The first will define the benchmark risk; the second should clarify how preliminary valuation gains translate into final net income and cash flow. Until then, Saylor’s $100,000 Bitcoin call remains just that – a forecast from a man with a substantial commercial interest in its outcome.

Correction: An earlier version of this article misstated the week-over-week change in Strategy’s Bitcoin purchases. It fell to $21.5 million from $28.7 million, not rose.