Back in the days of an unregulated stock market JFK’s father, Joseph Kennedy, built a family fortune through insider trading and real estate, among other shrewd business practices.

The Kennedy family is American royalty. John F. Kennedy, affectionately known as “JFK,” was the iconic American president–his life tragically ended much too soon, dashing hopes for a brighter future for so many Americans in 1963. Still, the Kennedys today serve the nation in various public service and voluntary roles, with much thanks to the fortune built by JFK’s father, Joseph Kennedy.

Kennedy family present for Joseph P. Kennedy, Sr.’s 75th birthday. Kennedy Sr. and Rose Kennedy pose with some of their children and their children’s spouses in the Kennedy home’s sunroom in Hyannis Port, Massachusetts. The group gathered to celebrate as follows: (L-R) Kneeling: First Lady Jacqueline Kennedy; Joseph P. Kennedy, Sr. (L-R) Standing: R. Sargent Shriver; Stephen Smith, Sr.; Ethel Kennedy; President John F. Kennedy; Jean Kennedy Smith; Rose Kennedy; Robert F. Kennedy; Eunice Kennedy Shriver; Patricia Kennedy Lawford; Edward (Ted) Kennedy; Joan Kennedy. (Photo: Stoughton, Cecil W.)

Members of the family have been congressmen, ambassadors and mayors. Given how interwoven the Kennedys are in the fabric of America, would you ever associate the Kennedy family with insider trading? The kind of insider trading that sent Martha Stewart to prison only several years ago?

Joseph Kennedy, the Business Man

A recent article in Forbes brings this realization to light. While it is well-known that the family is incredibly wealthy, a lesser-known fact is how they obtained their great billionaire fortune. JFK’s father, Joseph P. Kennedy, gained his wealth through insider trading. Later, he chaired the Securities and Exchange Commission (SEC).

Joseph Kennedy was a stockbroker in 1919, and the market was unregulated at the time. He became an expert and used tactics that are now considered market manipulation and insider trading. In 1923, he set up his own firm. He shorted stock during the 1929 stock market crash, and became a multi-millionaire.

Kennedy and several like-minded investors used tactics like creating a stock shortage to drive up their own holdings, as well as bribing journalists to present stock information in a very favorable light.

Joseph Kennedy and the Family Trusts

Since Joseph Kennedy first amassed the fortune, the family has kept it going by taking advantage of tax strategies and creating a multitude of trusts. The fortune is now dispersed among 30 family members, like the Smiths, Lawfords and Shrivers. The family’s wealth has been managed by Joseph P. Kennedy Enterprises in New York City since 1927. Investments are handled by outside firms, but family members serve on the board.

Joseph P. Kennedy was many things, but in particular, he was a shrewd businessman. It was his idea to put the money in trusts, and is the signature reason why the family still maintains the vast fortune today. Trusts are usually set up to prevent uncooperative family members from getting their hands on money; typically beneficiaries can’t get to more than 10 percent of holdings.

Trusts also prevent the government from getting their hands on the Kennedy money. They have set up a dynasty trust, which can be passed along each generation for decades. These trusts are not subject to any estate tax. In fact, a dynasty trust can potentially hold the un-taxable fortune forever. Joseph Kennedy knew that, and set up the first Kennedy trust in 1936.

Caroline Kennedy is by far the richest of the Kennedy children, with a fortune estimated at $175 million and growing. She is the only surviving member of her immediate family; JFK was her father, Jacqueline Kennedy was her mother, with her brother JFK Jr. tragically dying in a plane crash.

Chicago River Merchandise Mart

Not only are the family members politically savvy, but they are financially savvy as well. They avoid taxes like the plague, such as in the sale of a huge retail space on the Chicago River called Merchandise Mart, which was once the largest building in the world. They avoided capital gains taxes on nearly half the sale value. They also structured a deal whereby certain family members, including Caroline Kennedy and Maria Shriver, continue to collect millions of dollars of income from this sale, though it had occurred twenty years ago in 1998.

The Kennedys don’t talk much about their wealth. They describe themselves as a “very public family with a very private investment philosophy.” Politically they appear more publicly.

Joseph Kennedy the 3rd carries on the family political legacy, serving as the U.S. Representative from Massachusetts’s 4th congressional district since 2013. Some see him as a bright young politician with potential for the Democratic party.