Yesterday, Bloomberg had a very interesting article about Danielle Chiesi, a former analyst at New Castle Funds LLC. Chiesi has been charged by federal prosecutors and also by the SEC with obtaining hot tips from executives at technology companies and passing them along to other hedge fund managers, including Galleon Group’s Raj Rajaratnam. New Castle and the firms that she tipped off then allegedly profited by trading based on this inside information.

It is the manner in which Chiesi is said to have obtained her inside information from these executives that is so unusual, and that has me racking my brain for anything even remotely similar in the insider trading world. According to Bloomberg, Chiesi, “a blond, blue-eyed former teenage beauty queen” (see Chiesi’s pageant photo, via Dealbreaker), used her sexuality to build sources at male-dominated tech companies. She reportedly wore short skirts, low-cut tops and outfits such as a “tight red suit with red fishnet stockings” as part of her effort to develop her network, Bloomberg says. According to the article, one of Chiesi’s go-to “ploys” was to go barhopping with a group, and then peel a potential source off to talk to on the dance floor. “It amazes me that grown, wealthy, successful, hardworking men fell for that,” one investor relations executive told Bloomberg.

Although virtually every tactic imaginable has been used to obtain inside information through the years (e.g., hacking information sources; stealing advance copies of business magazines; betrayals by professionals such as therapists, lawyers, accountants; and investment bankers; betrayals by husbands, wives, bothers-in-law, and so on), “sexuality” has really not surfaced as a factor in insider trading cases.

Yes, James McDermott, the former CEO and chairman of investment bank Keefe, Bruyette & Woods, pleaded guilty to securities fraud and leaking inside information to his porn star mistress (who in turn leaked the information to another man with whom she was having an affair), but that doesn’t really hit the mark. And yes, one of the relief defendants in the recent “Golden Goose” insider trading ring led by Matthew Devlin was a Playboy Playmate, but again, not a direct hit.

In fact, the only other insider trading case that I can think of where sexuality was even an issue was the legendary case involving David Pajcin and Gene Plotkin. In that case, one of the many ways that these two men allegedly sought to obtain inside information was through the use of exotic dancers.  The SEC said that Plotkin and Pajcin actually tried to recruit exotic dancers in New York to obtain confidential information about upcoming deals from their Wall Street clientele. This part of their plan, however, apparently never got off of the ground. Thus, unless readers can add to this list, it appears that Chiesi’s tactics stand alone in the annals of insider trading history.