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MSTR’s worst drop since 1999 was 100%

Strategy (MicroStrategy) (MSTR) fell 100% from Mar 2000 to Jul 2002. It took 24.6 years from that peak to close at a new high, in Nov 2024. Over the same years the S&P 500 fell as much as 55%.

That drop ranks 3rd deepest among the 986 stocks PortfolioAutopsy tracks.

−99.9%
Worst drop
Mar 2000 → Jul 2002
24.6 yrs
Back to the old high
new high Nov 2024
−98.2%
Worst 12 months
Mar 2000 → Mar 2001
24.6 yrs
Longest underwater
from Mar 2000
−67.9%
Now vs its high
as of 2026-10-13
+8.7%
Yearly return since 1999
dividends reinvested

Drawdown from the last high, 1999 to now

MSTRS&P 500 (SPY)
MSTR drawdown from its last high since 19990%−25%−50%−75%−100%200020052010201520202025−100% by Jul 2002

How MSTR held up in each crash

CrashYearsMSTRS&P 500
Dot-com bust2000–02−99.9%−47.5%
Financial crisis2007–09−70.9%−55.2%
COVID crash2020−39.7%−33.7%
2022 rate shock2022−75.5%−24.5%

Each number is the deepest fall from a high inside that window, using daily prices with dividends reinvested.

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Questions

What was MSTR’s maximum drawdown?

MSTR’s deepest fall since 1999 was 99.9%, from its high on March 10, 2000 to its low on July 26, 2002. The figure uses daily prices with dividends reinvested.

How long did MSTR take to recover?

24.6 years. MSTR first closed above its Mar 2000 high again on November 11, 2024.

Was MSTR riskier than the S&P 500?

Over the same years, MSTR’s worst drop was 99.9% against 55.2% for the S&P 500 (SPY), and its worst 12 months were −98.2% against −47.4%.

Compare with

AIG −100%LCID −99%BKNG −99%AMT −99%MU −98%C −98%AMD −97%F −95%All tickers

Daily adjusted closes from Yahoo Finance, January 5, 1999 through October 13, 2026, dividends reinvested. Historical facts, not a forecast and not investment advice.

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