Has the S&P 500 ever lost money over a 15 year period?
No, across comprehensive historical market data tracking rolling 20-year holding periods of the S&P 500 with all dividends reinvested, the index has never lost money. Even for investors who invested at the absolute worst possible historical moments—such as right at the market peak preceding the Great Depression in 1929 or the extreme valuations of the year 2000 tech bubble—a 20-year time horizon was consistently sufficient for the market to recover, compound, and deliver a positive overall nominal return.
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