James McDermott, Keefe, Bruyette & Woods
Perhaps it was the irony of all ironies. In 2000, Canadian adult-film actress Marilyn Star made a film called Marilyn Whips Wallstreet, but Wall Street, or at least the Securities and Exchange Commission, had the last laugh.
In the late '90s, Star was romantically involved with James McDermott, CEO of the investment-banking firm Keefe, Bruyette & Woods. McDermott allegedly revealed details of an upcoming merger to Star, who passed the information to another lover, Anthony Pomponio. The two used the details to make more than $80,000 in the stock market. When authorities moved to arrest Star, she fled to Vancouver; in 2000 she was arrested and extradited to the U.S. After serving a few months in jail, Star was freed, but McDermott didn't get off so easy. He paid a reported $230,000 fine and served a short jail sentence himself. When asked by reporters if she had gotten into trouble because she was dating an older man, Star uttered words seldom heard in an insider-trading trial. "Older men like younger women because they are too dumb to stand up for their rights," Star said. "Instead of saying no, they say, 'Yes, Daddy. Yes, Daddy.' "