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3. Martha Stewart (Insider Trading)

Stewart has made a career out of giving good advice, but she definitely shouldn’t have taken certain advice from her broker back in 2001. Apparently she had some insider tip about ImClone, as she sold off stock just before the company announced a big set-back. Trading based on insider information is illegal, and so she was hauled up by the law. Despite maintaining her innocence, she was convicted and ended up with 5 months in prison, 5 months more of house arrest and 2 years probation.

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