Michael Saylor’s Strategy Bets $835M on the Bitcoin Dip as Crypto Market Slides Below $95K

MicroStrategy (MSTR) Stock Hits Fresh Lows as MSCI Exclusion Risk Grows and Bitcoin Slides – What Investors Need to Know Today (Nov. 20, 2025)

MicroStrategy’s parent company Strategy Inc. (NASDAQ: MSTR), still widely known by its former name MicroStrategy, is having another bruising session on Thursday, November 20, 2025. The Bitcoin‑heavy stock is trading near fresh 52‑week lows, faces the prospect of being kicked out of major MSCI indexes, and yet is still attracting big institutional buyers such as U.S. state pension funds. [1]

Below is a complete, news‑driven look at MSTR today for Google News and Discover readers.


MSTR stock today: price, range and volatility

By late trading on November 20, MSTR is changing hands around $178 per share, down roughly 4–5% from Wednesday’s close near $186.50. Intraday, the stock has swung between about $171.5 and $194.5, underlining just how volatile it has become. [2]

Key snapshot for Nov. 20, 2025:

  • Last price: about $178
  • Previous close (Nov. 19): ~$186.5
  • Intraday range: roughly $171.5 – $194.5
  • Two‑day move: from above $200 on Tuesday to the low $170s today
  • Market cap: in the low‑$50 billion range, depending on the data provider [3]

On Wednesday, MSTR hit a 52‑week low around $181.73 and closed near $186.50 after previously finishing at $206.80, according to MarketBeat’s alert. [4] Yahoo Finance data now show Thursday’s low near $171.48, marking yet another new low. [5]

Over a longer horizon, several analyses agree on the same message: the stock has crashed from its mid‑July peak, down 40–60% over roughly the past four months as Bitcoin rolled over from record highs. [6]

With a beta above 2.5, MSTR remains one of the most volatile large‑cap equities tied to Bitcoin. [7]


New 52‑week low – and a rare discount to the Bitcoin treasury

One of today’s most striking headlines: MSTR is now trading below the value of its own Bitcoin holdings, at least on a gross basis before debt. A CryptoPolitan report notes the stock has “crashed to [a] new 52‑week low, trading below the value of the BTC treasury.” [8]

Here’s why that matters:

  • Strategy’s own “Purchases” page and recent coverage indicate the company now holds about 649,870–650,000 BTC on its balance sheet. [9]
  • With Bitcoin currently around $86,700, that stack is worth roughly $56 billion at today’s spot price. [10]
  • Meanwhile, most data providers put MSTR’s equity market cap in roughly the $50–54 billion range today. [11]

That implies the market is valuing Strategy’s entire software business, its sizable analytics franchise, and other assets at close to zero – or even a discount – once the Bitcoin pile is accounted for, especially after factoring in convertible debt and preferred equity.

Earlier this month, CoinDesk noted that even after a sharp selloff, MSTR still traded at a premium to its Bitcoin holdings. [12] The fact that newer reports now highlight a discount shows just how fast sentiment has flipped.


MSCI index review: JPMorgan flags up to $8.8 billion in potential outflows

The other dominant story today is index risk.

MSCI has launched a consultation on whether to exclude companies whose digital‑asset holdings exceed 50% of total assets from its flagship equity indexes. Strategy (MSTR) is explicitly in the crosshairs. [13]

Key points from JPMorgan’s note and today’s coverage:

  • Strategy currently sits in heavy‑hitting benchmarks such as MSCI USA, MSCI World and the Nasdaq 100, making it a standard Bitcoin proxy inside many passive portfolios. [14]
  • Of an estimated ~$59 billion market cap, roughly $9 billion is held in ETFs and mutual funds that track these indexes. [15]
  • JPMorgan estimates about $2.8 billion in forced selling if MSTR is removed from MSCI indexes alone – and up to $8.8 billion if other index providers follow the same rulebook. [16]
  • MSCI’s decision is expected by January 15, 2026, following its current public consultation. [17]

Barron’s highlighted the irony: Strategy has never made it into the S&P 500 despite meeting size and liquidity tests, in part because it’s perceived as a quasi‑Bitcoin fund. Now it could be forced out of the MSCI indexes that helped mainstream it in the first place. [18]

CoinDesk further notes that Strategy’s combined equity + debt + preferred value relative to its Bitcoin holdings has fallen to the lowest level since the pandemic, and warns that a negative MSCI ruling could push that ratio close to 1:1, leaving the company priced almost purely as a Bitcoin tracker. [19]


State pension funds keep buying MSTR anyway

Despite the chaos, some deep‑pocketed institutional investors are doubling down on MSTR rather than walking away.

A CoinCentral report today reveals that Arizona’s $60 billion State Retirement System has bought roughly $15 million of MSTR, using the stock as a regulated, indirect way to get Bitcoin exposure. [20]

That article also highlights a broader trend:

  • 14 U.S. states now collectively hold more than $632 million in MSTR, with
    • California leading at about $276 million,
    • Florida around $88 million,
    • and other states gradually adding positions. [21]

For these funds, Strategy is still viewed as a “top Bitcoin proxy investment” that fits more comfortably inside traditional mandates than spot crypto, even as index providers and regulators grow uneasy with the model. [22]


Saylor’s latest message: “we can survive deep Bitcoin drawdowns”

Executive chairman Michael Saylor is leaning into the turbulence rather than backing away.

Recent commentary across several outlets paints a consistent picture:

  • In an interview highlighted this week, Saylor argued that Strategy could withstand an 80–90% drawdown in Bitcoin without abandoning its strategy, reassuring shareholders that extreme volatility is part of the plan. [23]
  • Investopedia summarized his stance by saying he feels “indestructible” despite the latest Bitcoin slide, underscoring his belief that Bitcoin’s long‑term trajectory remains intact. [24]
  • Benzinga today reports Saylor’s view that Strategy can continue to create shareholder value as long as Bitcoin grows at a healthy annual rate over time (he has often cited double‑digit yearly appreciation as sufficient). [25]

Meanwhile, the company has kept buying:

  • Over recent weeks, Strategy reportedly added 8,178 BTC (~$835 million) at an average price around $102,000 per coin, bringing holdings to roughly 650,000 BTC, about 3% of global supply. [26]

This aggressive accumulation, even into sharp drawdowns, is exactly why MSCI and some analysts see Strategy as a “passive Bitcoin hoarding” vehicle rather than a conventional software company. [27]


Wall Street is split: “Sell the rally” vs. 200%+ upside

Today’s research and opinion flow shows just how polarizing MSTR has become.

The bearish camp

  • A note on 99Bitcoins urges investors to sell MSTR on exit rallies and rotate into a new Bitcoin Layer‑2 project, arguing that the stock’s leverage to Bitcoin works both ways in a downturn. [28]
  • A Barchart analysis from last week points out that MSTR is down more than 40% over the last six months, calling into question whether the once‑popular Bitcoin proxy still justifies its volatility premium. [29]
  • StockTwits highlights a “Hotel California” dynamic, with 10x Research estimating that Strategy investors have absorbed roughly $20 billion in NAV losses since late 2024. [30]
  • Barron’s notes that some of Strategy’s convertible bonds now yield nearly 8%, a level more typical of stressed borrowers than a healthy tech firm, signaling growing credit‑market concern about the business model. [31]

StreetInsider’s options column today gives MSTR an overall analyst rating of “Sell (Flat)”, even as speculative flows remain heavy. [32]

The bullish camp

The bulls, however, are far from quiet:

  • TipRanks features a piece today titled “Time to Buy Strategy?”, noting that a top Bernstein analyst sees more than 200% upside in MSTR from current levels, effectively treating the selloff as an opportunity to buy a leveraged Bitcoin proxy at a discount. [33]
  • Benzinga’s data show a consensus Wall Street price target near $515 per share, far above today’s sub‑$200 quote. [34]
  • Insider Monkey still includes Strategy in its list of the “10 Best Crypto‑Related Stocks to Invest In” as of today, underscoring its continued appeal for hedge funds looking for high‑beta crypto exposure via equities. [35]

In other words, opinion is violently split: some see MSTR as structurally broken, others as a deeply discounted call option on Bitcoin’s next leg higher.


Options and sentiment: high implied vol, calls leading puts

Options activity today underlines the speculative mood:

  • StreetInsider reports that as of 2:18 p.m. EST, MSTR was trading around $177.34, down nearly 5%, with 30‑day implied volatility at 95 – an extremely elevated level that implies double‑digit daily price swings are on the table. [36]
  • The call/put ratio stands at about 1.5 calls for every put, suggesting traders are still willing to bet on upside despite the drawdown. [37]

Earlier this week, TheFly also flagged that options traders had grown “moderately bearish”, with skew steepening as demand for downside protection increased while volume remained massive. [38]

On the retail side, the dedicated r/MSTR subreddit continues to host a daily discussion thread for November 20, where sentiment appears mixed between long‑term “HODL” conviction and fatigue with the relentless volatility. [39]


The Bitcoin backdrop: testing the “max pain” range

Today’s MSTR story can’t be separated from what’s happening in Bitcoin itself.

  • Bitcoin is trading near $86,700, down sharply from this year’s highs and roughly 30% off its recent peak. [40]
  • AInvest calls the current $73,000–$84,000 zone a “max pain” range for institutions, noting that BlackRock’s IBIT ETF has a cost basis near $84,000 and MicroStrategy’s treasury cost basis is estimated around the low‑$70,000s. [41]

In this scenario, MSTR behaves like leveraged equity on a highly volatile underlying asset:

  • When Bitcoin falls, Strategy’s huge BTC stack and its debt‑funded purchases magnify losses.
  • When Bitcoin rebounds, the same leverage can work in the opposite direction – something MSTR shareholders have enjoyed in previous bull cycles.

Analysts at AInvest and Investing.com argue that recent volatility has exposed the limits of passive Bitcoin hoarding as a corporate strategy, but they also note that Bitcoin’s technicals now look oversold, leaving room for a sharp relief rally. [42]


Key catalysts to watch for MSTR

Looking beyond today’s tape, several catalysts are likely to drive MSTR over the coming weeks and months:

  1. MSCI’s digital‑asset consultation (near‑term)
    • Public feedback period is under way now.
    • A decision is expected by January 15, 2026; if MSCI confirms the exclusion, passive outflows could be measured in billions of dollars. [43]
  2. MSCI’s November index implementation (Nov. 24, 2025)
    • Broader index changes go live at the close on Nov. 24, which could further impact flows into and out of crypto‑linked equities. [44]
  3. Bitcoin’s path into year‑end
    • Whether Bitcoin holds above the $73k–84k institutional “max pain” band or breaks lower is likely to remain the single biggest driver of MSTR. [45]
  4. Convertible bond and preferred‑shares market
    • With some of Strategy’s convertibles yielding close to 8%, any further widening in credit spreads could pressure equity investors and constrain future balance‑sheet maneuvers. [46]
  5. Next earnings report (early February 2026)
    • Several calendars list Strategy’s next earnings date around Feb. 3–4, 2026, which will give investors fresh data on revenue from its analytics software business and any realized gains or losses on its Bitcoin trades. [47]

Bottom line: a high‑beta bet on Bitcoin and index politics

For November 20, 2025, the story around MSTR is clear but complicated:

  • The stock is near fresh 52‑week lows, and for the first time in this cycle appears to be trading at or below the market value of its enormous Bitcoin treasury. [48]
  • MSCI’s proposed index changes and JPMorgan’s warning of multi‑billion‑dollar passive outflows have added a powerful structural overhang to an already volatile name. [49]
  • At the same time, state pension funds and some top Wall Street analysts are leaning in, seeing MSTR as either a strategic Bitcoin proxy or a high‑conviction deep‑value play with triple‑digit upside potential. [50]

For traders and investors, MSTR today is not a simple “tech stock”. It’s a leveraged, index‑entangled macro bet on:

  1. The future path of Bitcoin, and
  2. How index providers and regulators choose to treat corporate Bitcoin treasuries.

That combination can be enormously rewarding in bull markets and brutally painful in drawdowns, as the last few months have shown.

Disclaimer: This article is for informational and news purposes only and is not investment, tax, or legal advice. Always do your own research or consult a licensed professional before making investment decisions.

How does MicroStrategy buy Bitcoin - Explained in under 3 minutes

References

1. www.barrons.com, 2. finance.yahoo.com, 3. stockanalysis.com, 4. www.marketbeat.com, 5. finance.yahoo.com, 6. www.investing.com, 7. www.marketwatch.com, 8. www.cryptopolitan.com, 9. www.strategy.com, 10. www.strategy.com, 11. stockanalysis.com, 12. www.coindesk.com, 13. www.investing.com, 14. www.coindesk.com, 15. www.coindesk.com, 16. www.theblock.co, 17. www.barrons.com, 18. www.barrons.com, 19. www.coindesk.com, 20. coincentral.com, 21. coincentral.com, 22. coincentral.com, 23. themarketperiodical.com, 24. www.investopedia.com, 25. www.benzinga.com, 26. www.ainvest.com, 27. www.investing.com, 28. 99bitcoins.com, 29. www.barchart.com, 30. stocktwits.com, 31. www.barrons.com, 32. www.streetinsider.com, 33. www.tipranks.com, 34. www.benzinga.com, 35. www.insidermonkey.com, 36. www.streetinsider.com, 37. www.streetinsider.com, 38. www.tipranks.com, 39. www.reddit.com, 40. stockanalysis.com, 41. www.ainvest.com, 42. www.investing.com, 43. www.barrons.com, 44. www.msci.com, 45. www.ainvest.com, 46. www.barrons.com, 47. stockinvest.us, 48. www.cryptopolitan.com, 49. www.barrons.com, 50. coincentral.com

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