insider-trading

Scandal erupted in the fantasy sports world earlier this week, when it was leaked that employees from one major fantasy sports website, DraftKings, had used their own inside information to win money in contests held by their rival company, FanDuel.

Now they’re both being investigated by the New York Attorney General’s office, which could potentially bring down the entire daily fantasy sports industry.

That got us thinking about other instances of people using inside information for their own benefit. While a story like this might be unusual for the sports world, it’s small potatoes in finance. Here are five of the biggest insider trading schemes Wall Street has ever seen.

1. Ivan Boesky

Boesky made a name, and massive fortune, for himself in the 80’s for being a genius when it came to takeovers. Too bad he got information from inside sources. At the time of his conviction Boesky was one of the richest and most powerful men on Wall Street. He ended up serving 22 months in prison.

2. Michael Miliken

Miliken was another star of 80’s Wall Street, at one point earning hundreds of millions of dollars per year as the king of junk bonds. He made his money much the same way Boesky did, and when Boesky ratted him out he was ordered to pay $1 billion in fines and sentenced to 10 years in prison.

3. Jeff Skilling

The Enron scandal was so bad that it remains a punchline almost 15 years later. The massive energy corporation went belly up after an investigation revealed massive fraud that included lying about revenue and hiding debt. Skilling, Enron’s CEO, knew what was about to happen, so he cashed out as he resigned his post. He’s been in prison since 2006 and could be out as early as 2017.

4. Martha Stewart

This one was pretty standard as far as insider trading busts go–except it involved a celebrity. Stewart went to prison for five months in 2004 after an investigation revealed she had sold a biotech stock with inside information back in 2001. This led to some odd public exchanges. When asked about it during a cooking segment for a morning show, Stewart responded, “I just want to focus on my salad”, and at a press conference Stewart said she didn’t anticipate being uncomfortable in prison because of her ability to fall asleep anywhere.

5. SAC Capital

This one was so big that the Justice Department described it as “substantial, pervasive and on a scale without known precedent in the hedge fund industry.” In 2013 the hedge fund was charged with a scheme spanning 10 years, during which they used inside information to make hundreds of millions of dollars. They eventually pled guilty, and founder Stephen A. Cohen agreed to pay the entire $1.8 billion fine himself–the largest insider trading fine in history.