MSTR Investors: Mark Your Calendars for Jan. 15 — Billions Could Be Wiped Off in 1 Day

By Rich Duprey Published Nov 23, 9:51AM EST

Quick Read

Strategy (MSTR) owns 649,870 bitcoin worth roughly $56B. That’s over 3% of all Bitcoin ever mined.
MSCI decides January 15 whether MicroStrategy can stay in major benchmarks. JPMorgan estimates immediate $2.8B of forced outflows if it is excluded.
Strategy has raised over $20B through convertible notes since 2020. Its average acquisition cost sits at $74,433 per Bitcoin. versus today’s $86,700.

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MSTR Investors: Mark Your Calendars for Jan. 15 — Billions Could Be Wiped Off in 1 Day — © 24K-Production / Shutterstock.com

Strategy (NASDAQ:MSTR | MSTR Price Prediction), the former business-intelligence software maker turned Bitcoin (CRYPTO:BTC) holding company, now owns 649,870 bitcoin worth roughly $56 billion at today’s price around $86,700. That’s around 3% of all Bitcoin ever mined and far exceeds the company’s $500 million annual software revenue. Since 2020, executive chairman Michael Saylor has treated Bitcoin as the company’s primary treasury asset, raising billions in convertible debt and equity to keep buying on every dip.

MSCI’s Sword Hanging Over MSTR

On January 15, 2026, index giant MSCI (NYSE:MSCI) will decide whether companies whose main asset is cryptocurrency — so-called “digital asset treasury” firms — can stay in major benchmarks like the MSCI USA and MSCI World. Strategy is the most prominent large-cap company that currently fails the proposed rules: Bitcoin makes up over 90% of its total assets and dwarfs operating cash flow.

If MSCI kicks Strategy out, passive funds tracking those indices would be forced to sell. JPMorgan estimates an immediate $2.8 billion of outflows, with a potential total of $8 billion to $9 billion if the Nasdaq 100 follows suit. That mechanical selling could impact Strategy’s stock price, pushing it far below net asset value (NAV).

MSTR’s Debt Stack Keeps Growing

Strategy has raised more than $20 billion through zero- or low-coupon convertible notes since 2020, including:

$2 billion 0% notes due 2030 (issued February 2025)
$1.75 billion 0.625% notes due 2028
Multiple smaller offerings maturing as soon as December 2025

These notes are convertible at premiums of 35% to 55% to the current stock price, giving bondholders cheap upside while Strategy gets near-free capital. The strategy works as long as Bitcoin keeps rising and the stock trades at a premium to its Bitcoin holdings.

When Bitcoin fell from $109,000 in late 2024 to $80,700 this past Friday, the market-cap-to-Bitcoin-held ratio collapsed from 2.5× to roughly 1.1×, making new raises harder and more dilutive.

Break-Even Math Is Still Comfortable — For Now

Average acquisition cost sits at $74,433 per Bitcoin. At $86,700, Strategy has an unrealized gain of 16.5%, or $12 billion. A drop below $70,000, however, would wipe out paper profits and force the company to post additional collateral on some debt facilities or face margin pressure.

In Strategy’s third quarter earnings call, CFO Andrew Kang countered that the company has “multiple levers” to manage liquidity, including at-the-market equity issuance and new preferred stock series (STRK 8%, STRF 10%), suggesting any fallout would be limited.

What Happens After January 15?

The best case scenario for Strategy is that MSCI grandfathers Strategy in or delays any changes. Passive inflows could resume, the premium re-expands, and the Bitcoin buying machine restarts.

The base case is that Strategy is excluded, which would trigger forced selling, likely causing the stock to trade closer to 0.8x to 0.9x NAV for months and making it more expensive for the company to raise new capital.

For Strategy, the worst case scenario is sustained Bitcoin weakness below $70,000 that coincides with exclusion, creating a feedback loop of selling and dilution that impairs the ability to hold all 649,870 BTC long-term.

Broader Context in Late 2025

Corporate Bitcoin adoption is continuing. Metaplanet in Japan, Strive (NASDAQ:ASST), and several smaller firms now hold BTC, but none approach Strategy’s scale. Spot Bitcoin ETFs (BlackRock‘s (NYSE:BLK) iShares Bitcoin Trust Beneficial Interest (NASDAQ:IBIT), Fidelity Wise Origin Bitcoin Fund Beneficial Interest (NASDAQ:FBTC), and others) have absorbed most new institutional money in 2025, reducing the relative appeal of leveraged plays like Strategy.

Meanwhile, the Trump administration has established a national Bitcoin reserve and promised lighter regulation, which could provide a strong tailwind starting the first quarter of 2026 — if Strategy survives until then.

Saylor remains unequivocal: “We are a Bitcoin operating company with a growing software business attached.” Whether that argument persuades MSCI, or whether Bitcoin simply needs to rally first, will decide if the largest corporate Bitcoin holder keeps its throne or faces the biggest test in its five-year transformation.

About the Author Rich Duprey →

After two decades of patrolling the dark corners of suburbia as a police officer, Rich Duprey hung up his badge and gun to begin writing full time about stocks and investing. For the past 20 years he’s been cruising the markets looking for companies to lock up as long-term holdings in a portfolio while writing extensively on the broad sectors of consumer goods, technology, and industrials. Because his experience isn’t from the typical financial analyst track, Rich is able to break down complex topics into understandable and useful action points for the average investor. His writings have appeared on The Motley Fool, InvestorPlace, Yahoo! Finance, and Money Morning. He has been interviewed for both U.S. and international publications, including MarketWatch, Financial Times, Forbes, Fast Company, and USA Today.