Greenwich: More crooks than perverts, but we do have both – what a town!

Here’s what you missed yesterday while you were busy with Mother’s Day:

Riverside resident Stephen Dent is in the news today because he was blackmailed by some sexy B&D babes he chatted up on line. 

The women called him “master.” He called them his “slaves.”

But the women Greenwich financial titan Stephen Dent met online clearly were the ones with the power.

They used that power to extract more than $200,000, which Dent gave them voluntarily in exchange for both online companionship and sex.

According to the report, Dent told police he paid “approximately $15,000” for one sexual encounter. He also told police that in the first eight months of 2007, he “spent approximately $200,000 on women that he has either had sex with or just met online.” The report said that he gave some of the money to women he didn’t have sex with because “they were down on their luck,” giving it “out of the goodness of his heart.”

No one who’s met him has ever accused Dent of being the sharpest pencil in the box, but this part should give hope to every moron in America: anyone,  even those with IQs of 73, can grow up to be rich!

A new extortion case

On Jan. 28, 2009, the FBI called Greenwich police to inform them of another apparent plot to extort Dent.

After talking to a different private detective hired by Dent, police found that just months after Sipel’s sentencing, Dent was back on 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.

According to police documents, Dent was also blackmailed for $9,000 by a third woman, but no charges have been filed in that case.

In the 2007 police report, police reference a copy of an e-mail they describe as “a standard form letter” which Dent would send to prospective companions. That letter was initially withheld, but received by Greenwich Time upon a second request, albeit in redacted form. Despite much of the detail being blacked out, it does shed light on some details of Dent’s arrangements:

“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.”

Net worth: About $100 million

According to town records, Dent resides on a private street in a gated house near the Cos Cob Harbor assessed at $4.5 million and owns his own investment firm, although he recently closed the doors of his office in Old Greenwich, in the same complex as the Greenwich Time office. Dent, who told police in 2007 that his net worth is approximately $100 million, is also the founding funder of the Greenwich Science Center, a nonprofit educational organization based in Stamford, which is now defunct.

Frederick said Dent is moving forward with support from his family and hopes his story will be a warning for others.

“He is fortunate to be able to rely on the tremendous support he has received from his wife and family and from his close friends,” Frederick said. “He further hopes the publicity this matter has received will be useful in teaching the public the dangers of Internet crime.”

Okay, Stevo, lesson noted. Thanks!

UPDATE: Hold on kids, better finish yur studies if you want to get rich. Turns out Stevo is a grandson of the DuPont clan, which probably explains how he got a leg up in the world, though hardly explains why anyone invested their money with him.

UPDATE II: I forgot to mention that Dent lives in the old dump near the end of Twin Lakes Drive (Gilliam lane, to those of us who remember the street before developer Jack Brod got pretentious). His house has been on the market for a year or so asking something like $12   15 million. My estimate of its value is in the mid- threes, which may explain why it hasn’t sold and perhaps sheds light on the fantasy world this man is living in.

32 Twin Lakes. 5,000 sq. ft., $15 million ask

32 Twin Lakes. 5,000 sq. ft., $15 million ask





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31 responses to “Greenwich: More crooks than perverts, but we do have both – what a town!

  1. Front Row Phil

    What a blog, Chris. You give us politics (local, national and international), philosophy, real estate, some mud and vitriol, and the very latest sleaze. Talk about a single news source! Thank you.

  2. anonymous

    His cash outlays are far less than what “conventional” Greenwich guys pay out in divorce (or carry as a balance sheet liability during marriage)

  3. Pingback: TheTradingReport » Blog Archive » "Slave" Girls Attempted To Blackmail Their $100 Million Investment Advisor "Master"

  4. pulled up in OG

    Almost $3000/sq ft . . . this guy’s been spankin’ his Monkey, alright.

  5. Veronique

    The Dents attended the same private school as my children up until they left two years ago (hmmm, at the same time as this whole situation started brewing). It’s no surprise that his wife Valerie is standing by her man as the Dents were known to be extremely money oriented. I’m sure that Stephen’s net worth has a lot to do with her decision to stay. I can’t imagine any woman swallowing the fact that her husband paid other women to perform sex acts. I used to envy the Dents their fortune until I heard a few comments from their son regarding how rich his father was. After reading this article it reminds me that money is truly not everything in this world.

    • christopherfountain

      Dear Veronique – we’ll let your comment slide this time – after all, you’re not Fake walt who needs constant monitoring, but I point out that “I can’t imagine any woman swallowing the fact that her husband paid other women to perform sex acts. ” is hardly approipriate for this family – oriented blog! : )

  6. Riversider

    No need to post – thought you might find this interesting.

    Click to access 85ap504.pdf

  7. mrs pauls


    looks like a nice house…

  8. Wally

    Nice house down at the end of the street that CF grew up on in Riverside. Nice deed-protected direct water views across a small cove and past Riverside Yacht Club toward NYC, but no frontage (was sold off by a prior owner). A special property, but not $15M without the direct frontage and a dock (also looks at mud at low tide).

  9. SizeBuyer

    Don’t most of them look at mud at low tide around here?

    • christopherfountain

      yes they do, Size, including mine. I love low tide, because the egrets, blue herons and the like come out to stalk the flats then, and it’s fun to watch. But the few deep water spots of waterfront command a real premium, and the Dent house isn’t one of them. And from his vantage point, all he can see at low tide is acres and acres of mud, stretching all the way accross the little cove it’s on. Not a $15 million view.

  10. SizeBuyer

    anyway what’s the scoop with lowther point? a lot of stuff going on down there…looks like it’s gonna be nice

    • christopherfountain

      My brother Gideon sold that land ($21 million or so) to his clients, who are a local Greenwich family. And yes, it should be a beautiful home. The old Lowther mansion was fun to look at from the outside but not much inside (even Greenwich Historical Society denied interest) due to various add-ons and such over the years. The trim, moldings and good stuff were saved and will reused in the new house.

  11. James O'Boston

    $15,000 is way, way too much to pay for sex. Have Steve give me a call. I can probably get him laid for half that, provided he’s not too fat or nasty.

    • christopherfountain

      I know he’s nasty, James, but I haven’t seen Dido recently so I can’t vouch for his weight.

  12. Stanwich

    The listing says $13.5m, probably reduced since you started blogging about it. But CF, “mid-three’s” for this place?! Really, c’mon. What the hell is that value opinion based on?

    • christopherfountain

      I have heard other opinions of value, some as high as $7 million. I look at the value of a 1 1/2 acre piece of land on a nice street with good water views and say, $3.5. I’d go as high as $5, if it weren’t priced so high now. I figure this place is going nowhere for a loooong time and the longer it sits, the less it’s worth.

  13. Stanwich

    Yeah, but this is stone and slate, it wouldn’t be priced at land value. It would be priced with a renovation in mind (assuming the place actually needs it).

    • christopherfountain

      I say it would be priced at the cost of removing the dumpsters filled with all that stone and slate but if you wanted to renovate it (and yes, it is in sore need of renovation), budget $2.5 million. Add that to $3.5 land, you’ve got $6 million sunk in the place and Bob’s your uncle.

  14. Cos Cobber

    I’m with Stanwich, seems like the place should easily fetch something north of $4m. But what would I know, I’m in a tar paper shack, on the wrong side of the road.

    PS – that lawn looks like a good place for an above ground pool.

    • christopherfountain

      I gotta believe that Valerie Dent quickly lost all interest in continuing to live in Riverside yesterday morning when the Greenwich Time landed on the Dent doorstep. That, plus what I would assume will be the pending divorce, and I smell bargain sale!

  15. Lorin

    so there’s no Gilliam Lane anymore?

    • christopherfountain

      h there is, it just stops at the top of the hill leading to “Twin Lakes” – which, as you may remember, are two little brackish ponds.

  16. R.S.

    Forget about his house!

    Has anyone ever cared to ask “why doesn’t the rich man have to face the law”? What he was doing was equally illegal, and apparently there was evidence to support that on three different cases. So why hasn’t he been arrested or charged? Why hasn’t ANY rich man in similar cases been charged? The bottom line is; this is a classic case of “If you are rich or wealthy, you are better than the average American. You are better than me or you. You can be O.J. or you can be God”.


  17. Lorin

    That we skated on in the winter, mad hockey at dusk…

  18. A friend of Steve Dent

    I spent a lot of time with Stephen Dent when he was a young man.

    DoughMan was one of the craziest, most outrageous, funniest people I’ve ever known. He definitely rubbed a lot of people the wrong way, including myself at times. He had a huge sense of entitlement and was quite self centered. But he could also be very generous. And boy, did we have a lot of laughs.

    Dent called himself the “Marine,” and when he was interested in something he could push himself with rare discipline. He was smart and quite knowledgeable. He also had a strange insecurity. He wanted to be the center of attention so much that he often did, or said, things that made people laugh at him, not just with him. He was constantly saying purposely shocking things, like “I’m so horny it’s unsafe to bend over around me” (taking the single-sex-boarding-school humor that was common in our group to the extreme).

    He talked about sex constantly. After a date he would routinely give you all the gory details — I mean, position-by-position — whether you wanted to hear it or not — and there were usually a lot of positions.

    Many of the women I know said they would never date a man as controlling as Dent.

    But despite all his strangeness, I really enjoyed the DoughMan. Per unit of time, he made me laugh as much as anybody I have ever known. He was a true “crazy man,” in the good sense of the phrase.

    I haven’t kept in touch with Steve. I don’t know if he has any outlets for his crazy humor. I can believe Greenwich society would have little place for the crazy Steve Dent I so enjoyed. (Maybe that’s one of the reason he’s been seeking out young chicks, so he can let the crazy man out of the box.) I don’t know how his increased wealth has changed him (if he is worth $100 Million, a good chunk of that probably has come from his own hard work, which is to be admired.).

    I hope he, his wife, and children recover from the extreme embarrassment of his current scandal. I don’t know the status of his marriage, so I won’t pass judgment on his infidelity. Most of us ordinary working stiffs don’t know the temptations from women that face a man with 100 million dollars. The only two times in my life that really smart, hot women came onto me with intense sexual urgency (something most of us men have little defense for) was when they mistakenly thought I was really rich.

    I hope DoughMan gets back to being the “Marine” and gets a productive focus for his energy. If he can’t stop his need for the young stuff (and many wealthy men can’t), then he should probably seek a European-like understanding with his wife about it, so he need not fear blackmail (and reward her and respect her for her tolerance); he should be more discrete; and he should be much more aware of the deep dangers of the internet. As the old adage goes — “Be careful of whom you get into bed with.” That’s doubly true if your bimbo’s know you’re worth a 100 million dollars. Be aware of the dangers of not only blackmail, but also disease and paternity suits.

    I summary, I wish the best for Stephen and his family. And I will always consider myself lucky to have known the DoughMan.

    A friend of Stephen Dent

  19. A friend of Steve Dent

    To be fair to Stephen Dent there are couple of things I should add to my first posting on this blog. My first posting centered on what a larger-than-life character Steve was — about some of the aspects of Dent that his old friends often talk about when the subject of Dent comes up, because they are so funny.

    But this is more to Dent than that.

    First, despite his normal macho, the-Marine, hard-head, sex-machine, humorously-in-your-face attitude, Dent could on occasion be surprisingly sensitive. I remember a couple of occasions when he tried to give me personal advice. When doing so he was restrained and soft spoken, sensitive to the fact that he might be overstepping his bounds or saying something that might offend me. He was trying to help me, and he was sensitive enough try to do it in a gentile way. And once he said these things he did not say them again.

    Dent was actually a quite emotional person, under his hard-guy attitude.

    Second, despite the blow-by-blow descriptions Steve would give about many of the women he went out with there were a few women about whom he never said anything the least bit disrespectful. If Steve really liked a girl, he would go off the prowl, and talk about her as if she were somebody REALLY special. That is the way he talked about Valerie when I knew him.

    Third, DoughMan has had a lot of good friends beside me, and he still does. His 30th birthday party at the St. Moritz was a big blast. I’m sure a lot of people there were just acquaintances out to enjoy a great party. But there was a considerable core of people there who liked and cared for Steve. And many of them still do.

    Steve was central part of an old gang of mine that wedding bells broke up a long time ago, but the members of that gang will always cherish their memories of the DoughMan.

  20. a friend of a friend

    I will give you some personal advice:
    Choose your friends wisely.
    If you were a friend of “Dido the DoughMan” that is an indication that you have not done so in the past. Did he pay you to go to his birthday also??
    I understand many of his “friends” were paid to attend.

  21. watcher

    Dents still at it 4 women and still trolling sites as of July 11 2009 when will he be charged

  22. watcher

    where did Dent and family disappear to lately …. SugardaddyLand?

  23. watcher
    check out who designed the website

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