Retiring in 1999: $1M fell to $995K on a 4% withdrawal

Retiring in 1999 with $1M and a 4% inflation-adjusted withdrawal, the portfolio was worth $995K after 27 years, as of the latest data. Its worst year was 2008, when the S&P 500 lost 35.2% including dividends. A 1999 retiree started near the top of the dot-com bubble, about a year before the S&P 500 began a 49% fall.