Wall Street RegretsThe regret calculator.
S&P 500 · peaks of 2000, 2007, 2021

The worst three moments to buy the S&P 500 — and what they returned

Buy the index at the month-end close immediately before each of the last three great crashes, and hold. No skill, no timing — perfect anti-timing.

EntryThenTodayTotal return
2000-08$1,518$5,079+408%
2007-10$1,549$4,975+397%
2021-12$4,766$1,617+62%
Worst entry of the three2021-12It still became$1,617Best entry of the three2000-08

Every one of these entries was followed by a crash. Every one of them is dramatically in profit today. "Time in the market beats timing the market" is not a slogan — it is the output of this calculation.

FAQ

How is this number computed?

The figure uses the same historical closing-price data as the calculators: the relevant ticker's month-end close at the scenario's start, compared with the latest available month-end close, with splits and dividends handled per the methodology page.

What if I change the amount?

Every figure scales linearly: double the starting amount and every dollar figure doubles. Use the ticker's calculator page for exact-date precision and dollar-cost averaging.

Is this investment advice?

No. These are historical calculations for entertainment and education. Past performance never guarantees future results.

Every figure is computed from the same historical data the calculators use (see methodology). Not financial advice.