Buying at the Top: What Happened Next

By Chris Murray · Published Sep 23, 2026 · Updated Oct 3, 2026 · 3 min read

Suppose you put $10,000 into an S&P 500 index fund on the worst possible day: the market's high, just before a crash. This article walks through four of those days. Each chart follows the $10,000 from the day it was invested. All figures include reinvested dividends and are valued at the September 22, 2026 close.

1987: Black Monday

Bought August 25, 1987, the S&P 500's high that year. Stocks had risen nearly 40% since January. On October 19, a wave of automated selling by large funds, known as portfolio insurance, turned into panic, and the Dow Jones fell 22.6%, still its largest one-day percentage drop.

That day the S&P 500 fell about 20%, and the $10,000 was worth $6,692.

It was back to $10,000 by May 1989, dipped below again in 1990, and stayed above from November 1990, about three years after the purchase. By September 22, 2026, it was worth $496,292.

2000: The dot-com peak

Bought March 24, 2000. Through the late 1990s, investors poured money into internet companies, many with little or no profit, and the Nasdaq rose more than fivefold from early 1995 to its March 2000 peak. When many of those companies ran short of cash, the bubble burst, and the decline deepened after the September 11, 2001 attacks and the accounting scandals at Enron and WorldCom.

This one fell twice. By October 2002, the $10,000 was worth $5,248. It recovered to $10,000 in October 2006, then fell again in the 2008 financial crisis (covered in the next section), reaching $5,150 in March 2009.

It stayed above $10,000 from December 2011, almost 12 years after the purchase. By September 22, 2026, it was worth $80,368.

2007: Before the financial crisis

Bought October 9, 2007. Banks had made and traded large volumes of risky mortgages. When US home prices fell, losses spread through the financial system, Lehman Brothers collapsed in September 2008, and the US entered its deepest recession since the 1930s.

This was the deepest drop of the four. On March 9, 2009, the $10,000 was worth $4,481, a loss of 55%.

It was back above $10,000 in August 2012 and stayed there from November 2012, about five years after the purchase. By September 22, 2026, it was worth $69,930.

2022: After the pandemic rally

Bought January 3, 2022. Stocks had surged through 2020 and 2021 on low interest rates and pandemic stimulus. In 2022, US inflation reached a 40-year high, and the Federal Reserve raised interest rates at its fastest pace in decades.

Higher rates pulled stock prices down through most of the year. The low came on October 12, 2022, at $7,550.

The investment was back above $10,000 in December 2023, about two years after the purchase, and stayed there. By September 22, 2026, it was worth $17,249.

Single stocks don't always come back

An S&P 500 fund holds about 500 companies, so gains in some can offset losses in others. A single stock has no such cushion. The chart below follows $10,000 in three well-known stocks, each bought at its own peak, for the next five and a half years.

Cisco, bought March 27, 2000, was worth $2,254 five and a half years later. It did not stay above $10,000 until 2024. Zoom, bought October 19, 2020, was worth $1,600 on September 22, 2026. Peloton, bought January 13, 2021, was worth $300.

Summary

$10,000 invested on each date, valued September 22, 2026, dividends reinvested. Recovered: when the investment got back above $10,000 and stayed there.

The 1987 figures use the Vanguard 500 Index Fund (VFINX), since the SPY fund started in 1993. The other S&P 500 rows use SPY.

In all four cases, the index recovered and went on to grow. The cost of buying at the top was time, from about two to twelve years. For how the starting year affects results more broadly, see When Should I Start Investing?

Curious how a different start date would have played out? Pick any date in the calculator.