One of the biggest insider of all time seems to be ... the father of John kennedy, Joseph Kennedy who even after all his crimes was appointed SEC Chairman later by Roosevelt 
!!!
From:
Cecil Adams's "Return of the Straight Dope" (ISBN 0-345-38111-4)
"...he set about mastering the secrets of insider trading, management pools, and selling short. Soon he was hhead of the stocks department and on his way to his first million..." [p. 41]
"Joseph P. Kennedy had made his first big killing in the winter of 1923. For an outlay of only $24,000---on credit---he'd used insider information given him by Galen Stone and had reaped a profit of more than a half a million dollars---$675,000---in fact---on Pond Creek Coal Company shares. [...] Sitting in his office, [...] Joe Kennedy now indulged in financial larceny on vast an unseen scale, manipulating share pricess with other hands in secret stock pools designed specifically to hoodwink investors. His growing expertise neeted him a second fortune in the spring of 1924..." [p.51]
Joe's further dealings are many and varied, including film deals, and not all as profitable as the insider trading. He also tried to become a wire-puller in politics, and helped to elect Roosevelt president in 1932.
"...November 1933. Mr. Kennedy had abandoned plans to see Mussolini. Instead, having used Jimmy Roosevelt to open doors that would have otherwise been closed to him, Kennedy managed to obtain the exclusive United States distributership for Haig & Haig, Gordon't Dry Gin, Pinchbottle, and other British liquors in anticipation of the repeal of Prohibition." [p. 101. Footnoted as coming from David E. Koskoff, _Joeseph P. Kennedy_ (Englewood Cliffs, NJ, Prentice Hall, 1974]
And finally, a little irony:
"On June 28, 1934, President Roosevelt finally rewarded Kennedy for his work in the 1932 election campaign. Countering all objections with the words "it takes a thief to catch a thief," he appointed Joeseph P. Kennedy the first chairman of a new regulatory agency to tidy up the nation's stock market: the Securities and Exchange Commission, or SEC. To the consternation of all, the notorious stock-market swindler Joeseph P. Kennedy would become stock-market reformer." [p. 109]
!!! From:
Cecil Adams's "Return of the Straight Dope" (ISBN 0-345-38111-4)
"...he set about mastering the secrets of insider trading, management pools, and selling short. Soon he was hhead of the stocks department and on his way to his first million..." [p. 41]
"Joseph P. Kennedy had made his first big killing in the winter of 1923. For an outlay of only $24,000---on credit---he'd used insider information given him by Galen Stone and had reaped a profit of more than a half a million dollars---$675,000---in fact---on Pond Creek Coal Company shares. [...] Sitting in his office, [...] Joe Kennedy now indulged in financial larceny on vast an unseen scale, manipulating share pricess with other hands in secret stock pools designed specifically to hoodwink investors. His growing expertise neeted him a second fortune in the spring of 1924..." [p.51]
Joe's further dealings are many and varied, including film deals, and not all as profitable as the insider trading. He also tried to become a wire-puller in politics, and helped to elect Roosevelt president in 1932.
"...November 1933. Mr. Kennedy had abandoned plans to see Mussolini. Instead, having used Jimmy Roosevelt to open doors that would have otherwise been closed to him, Kennedy managed to obtain the exclusive United States distributership for Haig & Haig, Gordon't Dry Gin, Pinchbottle, and other British liquors in anticipation of the repeal of Prohibition." [p. 101. Footnoted as coming from David E. Koskoff, _Joeseph P. Kennedy_ (Englewood Cliffs, NJ, Prentice Hall, 1974]
And finally, a little irony:
"On June 28, 1934, President Roosevelt finally rewarded Kennedy for his work in the 1932 election campaign. Countering all objections with the words "it takes a thief to catch a thief," he appointed Joeseph P. Kennedy the first chairman of a new regulatory agency to tidy up the nation's stock market: the Securities and Exchange Commission, or SEC. To the consternation of all, the notorious stock-market swindler Joeseph P. Kennedy would become stock-market reformer." [p. 109]