Retiring in 1987: $1M grew to $27M on a 4% withdrawal

Retiring in 1987 with $1M and a 4% inflation-adjusted withdrawal, the portfolio was worth $27M after 39 years, as of the latest data. Its worst year was 2008, when the S&P 500 lost 35.2% including dividends. On October 19, 1987, known as Black Monday, the S&P 500 fell 20.5% in a single day, its largest one-day percentage drop on record.