The Worst Times to Invest (and Why It Didn't Matter)
Every investor's worst fear: putting money in right before a crash. We looked at three of the worst possible entry points in recent history to see what would have happened if you held on.
January 2000: right before the dot-com bust
The S&P 500 dropped nearly 50% over the next two and a half years. Tech stocks were hit even harder. But $1,000 invested in the S&P 500 in January 2000 would still be worth over $8,600 today. That's a 760%+ return despite the worst possible timing.
Even more striking: $1,000 in Apple in 2000 would be worth over $393,000 today.
October 2007: right before the financial crisis
The S&P 500 would go on to lose 57% from its peak to its March 2009 low. Banks collapsed. The housing market imploded. It felt like the end.
But $1,000 invested at the 2007 peak in the S&P 500 would still be worth roughly $6,900 today. Not as dramatic as the 2000 example, but still a solid 590% return for an investor who simply held on.
February 2020: right before COVID
The market dropped 34% in about five weeks. The fastest bear market in history. But $1,000 invested in the S&P 500 in January 2020 would be worth over $2,500 today, and anyone who bought during the March 2020 low did even better.
The pattern
In every case, holding for at least 5 years produced positive returns. The stock market has recovered from every crash in history. The only investors who locked in permanent losses were the ones who sold.
Meanwhile, $1,000 kept in cash since 2000 would have the purchasing power of about $510 today. Doing nothing was the worst strategy of all.
Browse all investments to see how different stocks performed through these downturns.
Related: Lump sum vs dollar-cost averaging - sidesteps the "wrong entry point" problem entirely. And gold vs the S&P 500 during the 2026 tariff shock - the most recent example of stocks selling off and a safe haven outperforming. See also what buying the S&P 500 right after the Liberation Day crash returned. For the calendar-based version of mistimed investing, see what selling in May every year actually does to a portfolio. And for the flip side of mistiming, see what investing at the very bottom of the 2020 crash would be worth today. For a current example of a scary entry that recovered fast, the S&P 500 mid-year 2026 report card shows a March dip into the red erased by an April rally.