The Curious Relationship of Joseph Kennedy, Sr. and Franklin D. Roosevelt

Joseph P. Kennedy was a bank president at the age of just 25. JFK Presidential Library

2. Joe Kennedy began investing in real estate while still working as a bank examiner

Kennedy’s position as a state bank examiner allowed him access to information which was nearly priceless from a standpoint as an investor. Examination of bank records gave him information on the financial condition of depositors, the status of mortgages and other loans, and which companies had been developing new products and services ready to bring to market. He bought control of a real estate firm in Boston called Old Colony Realty Associates. Through it he purchased financially distressed properties in or near foreclosure, and resold them profitably. His investment in the firm paid substantial dividends.

The real estate investments led to a growing interest in the stock market following the First World War. During the decade known as the Roaring Twenties, a period during which many still believe and repeat that Kennedy was a bootlegger. There is simply no physical evidence that Kennedy participated in the illegal liquor trade, and the anecdotal evidence is all based on questionable sources. The stories didn’t begin to appear until the 1950s. During the 1930s, Kennedy was thrice confirmed by the Senate for government positions, following an investigation into his background, conducted by committees which included politicians’ hostile to the president. None of the committee records show any evidence he was suspected of bootlegging.