“Kennedy made a large fortune as a stock market and commodity investor and by investing in real estate and a wide range of industries. He never built a significant business from scratch, but his timing as both buyer and seller was usually excellent. Sometimes he made use of inside information in ways which were legal at the time but were later outlawed. He later became the first chairman of the SEC. After his death, various gangsters including Frank Costello claimed to have associated with Kennedy. According to some accounts, Kennedy was associated in the “bear raid” that precipitated the Wall Street Crash of 1929, as well as much of the bootlegging activity that was common at the time. When Fortune magazine published its first list of the richest people in the United States in 1957, it placed him in the $200–400 million band meaning that it estimated him to be between the ninth and sixteenth richest person in the United States at that time.”
So we see why he had the time and resources to continue to interfere in politics for his family and friends:
“After graduating from Harvard in 1912, he took his first job as a state-employed bank examiner. This allowed him to learn a great deal about the banking industry. In 1913, the Columbia Trust Bank, in which his father held a significant share, was under threat of takeover. Kennedy, borrowing $45,000 ($1,058,182 today) from family and friends, bought back control and at age 25 was rewarded by being elected the bank’s president. Kennedy told the press he was “the youngest” bank president in America.”
His criminal activities continued with his career on Wall Street:
In 1919, he became an expert in dealing in the unregulated stock market of the day, engaging in tactics that were later labeled insider trading and market manipulation. In 1923 he set up his own investment company, becoming a multi-millionaire during the bull market of the 1920s, and even more wealthy as a result of taking “short” positions in 1929.”
After amassing multiple fortunes, he turned his attention towards the film industry where he played the merger game, and played Alexander Pantages, and Gloria Swanson, and cleverly played his fellow investor into allowing him to amass millions upon millions in acquisition deals, the result of which was a more centralized and tightly controlled Hollywood movie industry.