Back in 2009, Thomas Ammann found out through his investment banking job that Canon Inc would be acquiring a Netherlands-based company called Océ N.V. Being in a bit of a tight spot with his finances and seeing an opportunity to score some cash but wanting to avoid the prison time that could come with, he decided to be smart about things and put some distance between the tips and his profits, by employing a couple middlemen. In this case, those middlemen were his two girlfriends, Christina Weckwerth and Jessica Mang, who 1) put up the cash and 2) traded on the material non-public information. And while they probably would have taken issue with Ammann dating and tipping both of them, and would have perhaps been branded a lowlife by their friends and families, Tommy-boy made sure to keep the women a secret from one another, therefore only incurring the wrath of Mang's roommate on account of the insider trading business. Which, to be honest, Mang thought she was kind of being an uptight bitch about.

Mang bought OCE shares and then sold them five days later for almost twice what she invested, Pinto said. She wrote in her personal diary that Ammann advised her to invest, according to the prosecutor. Mang had been living in central London with a friend who worked in hedge-fund sales for Goldman Sachs, Pinto said. When told about Mang’s plans to invest in OCE, her friend “expressed her disapproval and kept calling it insider dealing.” In her diary, Mang wrote of her annoyance that her roommate insisted the trades were insider dealing. “Really?” Mang wrote, according to court documents. “Is that necessary? Increasingly prissy.”

Ex-Banker Girlfriends Double Money On Insider Trading [Bloomberg]
Investment banker 'helped two lovers (who had no idea the other existed) make £2million by leaking confidential information during takeover bid' [DM]