Back in 2007 Stephen Dent hopped on SeekingArrangement.com to seek out an arrangement wherein as a "sugar daddy" he would pay a "sugar baby" for "companionship." The testimonial at left from a man who offers "successful CEO" as his job title let Dent know the place was legit. He started chatting up some ladies, and after establishing a rapport, would make the bold move to take this thing offline. Dent being a prudent businessman, though, he took some precautions first. Here's the form letter he'd send to prospective real-life companions:
"I can only meet during the weekdays around midday. In general I am not available at night or during the weekends. Furthermore, we would need to meet only when my wife is away. Since I don't really travel, for the most part the meetings would have to be out here in the Greenwich-Stamford area.
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."
Imagine Dent's surprise when he found out some of the companions he met online were taking him for a ride! After being fooled the first time (and the subsequent arrest of his lady-friend's pimp/husband), a hardened Dent laid low for a while, but after a few months, he started getting that sugar baby itch again. He needed to scratch but rather than simply take a walk down to one of the seedier areas of Stamford, or use an alternative prostitution-lite site, such as SugarDaddy.com, Dent decided to return to the scene of the crime. Don't worry, though, he changed his account and registered e-mail. He's not stupid or anything. I mean, he did continue using the same screen-name but why should that matter? How else would his prostie friends know he was back in action?
...just months after Sipel's sentencing, Dent was back on SeekingArrangement.com again, this time with a new account, but still corresponding with the same women. "He closed his previous account and began to use a different e-mail address but the same screen name to correspond with his women friends," police documents state.
Dent's Internet chats once again turned ugly when Dawn Jessop, 28, of Ohio, allegedly began blackmailing Dent in November 2008, threatening to release their correspondence and expose Dent to the community for his alleged role in "patronizing prostitutes," according to police documents. Dent then wired two $25,000 payments to Jessop and her mother, and another $50,000 to her husband, Christopher Jessop. It was not until the FBI began to survey Dent's arrangements to drop $50,000 in the Jessops' account in January 2009 that Greenwich police were called to intervene, according to the warrant.
The Jessops currently face charges of first-degree larceny by extortion and first-degree conspiracy to commit larceny. Dawn Jessop was released on bond last week but her husband is being held on $300,000 bond at the Bridgeport Correctional Center.
According to police documents, Dent was also blackmailed for $9,000 by a third woman, but no charges have been filed in that case.
For the many of you reading who identify with Dent's situation but have been too scared to come forward, either because you're nervous about legal proceedings, or embarrassment, or how your hedge fund's clients might judge the situation-- do not fear. Big D is being treated as a victim, and "the decision not to investigate Dent also partly rested on the fact that police did not want to deter other victims of extortion from coming forward." There's nothing to be afraid of. We're good listeners and want to hear your stories.