Joseph Kennedy Sr., starting from a solidly middle class family in Boston, created a fortune that gave his children and grandchildren the freedom to pursue public service. Kennedy’s business ventures included banking, stock trading, producing movies and selling liquor. He thought to get out of the stock market before the crash of 1929 — after the major devaluation of everyone else’s portfolios, his family was only more wealthy during the Great Depression, in the 1930s.

Real Estate
The Kennedy real estate holdings became legendary: family compounds at Hyannis Port on Cape Cod, and in Palm Beach, Florida, as well as homes outside New York City. Joe Kennedy held a majority ownership in the Hialeah Race Track in Miami. In 1945 Kennedy formed a trust to buy the Merchandise Mart, an enormous sales center in Chicago built by Marshall Field, which was the world’s largest building at the time.

Hundreds of Millions
Joe Kennedy’s money may have had unsavory sources as well. He is rumored to have imported liquor during Prohibition, working with mobsters in that industry (he later sold his legitimate liquor importing business to a known mobster named Abner “Longy” Zwillman). Joe Kennedy never publicly revealed his wealth, but the New York Times estimated his net worth at $500,000,000 when he died in 1969.

Donated Salary
Unlike their father, none of Joe Kennedy’s sons went into business. Instead, they pursued his dream: elected office. As a young man, John F. Kennedy never seemed to carry any money with him; friends knew to pay the tab and send the check to Joe’s office to be reimbursed. As one of the wealthiest presidents of the United States, Kennedy donated his salary — $100,000 a year — to charity.

Millionaires’ Club
Many wealthy Americans are in politics today, making the Kennedys’ fortune seem less noteworthy. By 2003, Edward Kennedy was just one of 40 millionaires in the U.S. Senate. His net worth, disclosed at over $9.9 million, placed him in the top ten but well below his colleague from Massachusetts, John Kerry, whose $163.6 million topped the list.

Smart Investing
In 1998, Merchandise Mart and other properties were sold for $625 million — a 50 year return on profit of nearly 2,000%. The Merchandise Mart was the last business the Kennedy family owned; its assets are now primarily in the form of securities. In 1990, before the stock boom of that decade, Forbes estimated the family’s wealth at $850 million.