Greenwich Financier Stephen Dent Teaches Us About When Gold-Digging Becomes a Crime

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Photo: Seeking Arrangement

Some people don't learn lessons. Other people are very good at learning lessons. The story of Stephen Dent, a 54-year-old multimillionaire DuPont heir, includes both groups. Primarily, Dent is the one here who doesn't learn. After getting blackmailed by a woman he met on the sugar-daddy website SeekingArrangement.com (sample testimonial: "Unlike other cash strapped students, I am pampered with expensive gifts. My sugar daddy is the sweetest man I know. He is my mentor, my benefactor and my lover"), the married Dent went back on the site only to get blackmailed again. And then once more again. And this was after the FBI and private investigators were involved the first time around. All told, Dent spent about $200,000 on women from the site, and was blackmailed for $150,000 more.

So, here's the guy who wasn't learning his lessons. Who was?

The sugar babies, of course! Here's a sample ad that Dent posted for potential job applicants:

"Regarding your financial assistance, my initial thoughts are cash compensation in the range of $2,000 to $3,000 per meeting, assuming that we meet about twice a month, plus expenses. If there is anything of an impersonal nature (such as electronics items) that you would like me to purchase for you online and have shipped to your home, I'd be happy to do this. If you are interested in relocating, I will pay for your moving expenses and switch you over to a monthly allowance which would cover your expenses. If you have other financial needs, I'd be happy to discuss them. I am flexible on this whole subject, and am even willing to wire money directly to your checking account if needed."

Even though the website boasts women who "are college students, aspiring actresses or someone just starting out," more than one of them was smart enough to know a bottomless well of money when they saw one.

For Greenwich financier, online chats, trysts bring repeated blackmail [Greenwich Time]