Sextortionist’s Private Emails to Angry Ex
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- December
- 7
You can also call her The Punisher. At least, that’s the message conveyed in a series of emails between Jessica Wolcott and ex-husband Kyle Strait, in which the now-infamous Sextortionist says, “I punish people who cheat.”
Of course, the would-be vigilante has a few demons in her closet—as all vigilantes must. This we learned when Strait, an Airforce staff sergent (see pic of him with Inside Edition’s Lisa Guerrero here), explained to us in a phone interview that Wolcott repeatedly cheated on him during their marriage, often with multiple men at the same time.
No matter. She’s a crafty one, that Punisher, and she tries a number of tactics to scare her former husband out of blabbing further to the media, including (a) threatening to “out” a “relationship” that he had with another woman, (b) saying “the airforce is going to be asked for comment and I’m afraid there would be a repercussion for you … the last thing I want is you to be punished in your career now for the past,” and (c ) suggesting that Strait’s current girlfriend would be dragged into all this.
Almost all of Wolcott’s threats are posed in the form of questions, and while her powers of persuasion are clearly diminished in email form (exhibit A: Strait forwarding all of their correspondence to Suburbarazzi), the messages do provide a fascinating look how she coyly phrases her blackmail.
The full emails exchange is after the jump. We took the liberty of putting it in chronological order and highlighting some of the best parts. No matter how troubled your own relationships may seem, trust us, reading this is guaranteed to make you feel better.
NOTE: At Strait’s request, all names—other than Jessica Wolcott’s and Kyle Strait’s—have been removed. In the emails, Wolcott asserts that Strait had an affair with “That girl,” who Stait says was his best friend at the time.
From: Kyle——————————————-
To: Jess————————————————-
Sent: Fri, 1 December 2006 5:30 PM
Subject: dang youOk, so I know you’re in a s—t load of trouble but I do want to talk to you. How many people in your life can really say they as much about you as I do? Well, it looks like everyone knows these days but as excited and fulfilled this has left me, I want you to try and understand that it’s not completely under the condition that I am filled with spite for you. I see an opportunity in this Jessica. I’ve always known the way you were going to run with your life, ever since you were lying about XXXX. I knew you had a serious problem and that it may be the hardest habit you will ever break in your life. You lied to me about changing but I wanted to believe b/c there is hope in this world. Heck, you were the one that taught me about hope. Well, at least whoever you were being at the time did. I’m still having a hard time establishing your reference personality here though. Maybe you could help me with that. Could you do it honestly I wonder? See, if all you do is pretend to be a bunch of things you’re not, what are you really? See my problem here. You’re not a millionaire. You’re not hanging out with celebrities. You’re not a chemist. You’re friends don’t even know who you are. At least, if they did, I wouldn’t think they would be friends with you. And if they did, those aren’t good friends. Jessica, I think it’s time you take this matter and let it knock you down as low as you can go b/c you need to look up. Stop looking at all the things you are not. Stop trying to be the things you wish. Look at who you really are. Look deep. There may be a VERY ugly person inside but you need to face her. You have to ADMIT something is wrong with you. It is so hard to do but you have too. Jessica, you are only 22 and you’re headed for a life in jail b/c of using and ruining people. Is that what you want to be? If it is, than I take back all I say b/c you are truly sick beyond being a real person. But Jess, if you know you’re wrong, and you can admit your wrong, take the psych eval you are getting SERIOUSLY!!!!! There is no better time in your life to make a change than now. You had two opportunities two stop your ways with me previously and you obviously didn’t take advantage of that but now is your time. Don’t let it go further. I’m pulling for you here. I want to see you make a change. And if it’s not too much to ask, read the sermon on the mount. Mathew 5-7. I know you’re not religious but Jesus describes how we should live our lives in that and it NOT wrong just cuz it’s in the bible by any means. It is VERY true. If you committed yourself to living how He describes life in those chapters, you be the most successful person on earth.
KyleFrom: Jess——————————————-
To: Kyle————————————————-
Sent: Mon, December 04, 2006 12:08 PMI’m not angry with you in the least. Yes my friends are still there for me and yes “her current boyfriendâ€? is still here as he’s always been. This brings something unfortunate for us both. I have to give the media “my side” in a few months but we’ll be going on television to a much more reputable source than the NY Post (National Enquirer ish). It’s in my best interest and the judge will be more empathetic and lenient with my sentence if I “out” your relationship with “That girl and another twoâ€? etc… The prosecutors will use your story against me in a harsher sentence. Now obviously most of those wont matter other than “that girlâ€? because we were married. The airforce is going to be asked for comment and I’m afraid there would be a repercussion on you? Please realize I could have said nothing but the last thing I want is you to be punished in your career now for the past. Is the statute of limitations up so that you would not get into trouble? Is there some how I can get around it? I will try to leave “That girl’sâ€? last name out of it and perhaps that would give the airforce nothing to look her up on? I’m really not sure yet and it will be a few months. Maybe you can talk to a legal advisor in the military and let me know? Thank you.
JessFrom: Kyle——————————————-
To: Jess————————————————-
Sent: Tue, 5 December 2006 10:50 AMYou aren’t supposed to be on a computer there missy.
Well, it’s obvious that your “friends� don’t know what you are really like if they are standing behind your lies. This leads me to the conclusion that you are still just lying to everybody and there is really not much sense in trying to talk you out of your ways. I hope you break down the walls you’ve put up some day. Till then, I cannot be friends with you. I can only hope for the best and that you get help. I care about you Jessica. I care to see you make it out of this.
The court isn’t going to care about who I was dating back when I first met you. So, I was “sort of� dating two other people before I decided I wanted to go totally exclusive with you. Can’t imagine what I was thinking. Most everyone in the world does that. Yea, I could have told you, but then I would have had one less option. I still chose wrong obviously. That’s just high school drama anyways.
The “that girl� thing, well, that was all up to your imagination and whatever she was trying to pull over on you unfortunately. Otherwise, I had kicked you out of the house and my life so, what matters about the rest of the situation? I snuffed it and asked you to come back. I WANTED a real relationship with you after I found out everything. Do you know how stupid that was? All you did was use me from then on. I really thought you could make a change after being caught Jessica. Otherwise I never would have made that phone call and asked if you were ready to do things right the next time. Then, it was right back to lying. I hope you know that this all still upsets me for some reason. I know that it’s in the past but I still feel very wronged by you. I have forgiven you but the sorrow remains.
Jessica, I have to ask even though I can’t believe you. Was any part of our marriage even real to you? Or was I just another safety net for you to make a living? Like you’d admit the latter. Nevermind.
Anyways, why would you be working to get a lesser sentence? Don’t you think it’s time you reap? Don’t you think you deserve this? Are you so self centered and absorbed that you believe you didn’t have this coming? Jessica, you use people and lie about everything. Do you care about other people’s emotions?! Do you have ANY empathy yourself? You threatened to ruin a guys, probably multiple people, entire life just so you can throw money around and make people think you’re rich. Do you not see the magnitude of this? You need help.
From: Jess——————————————-
To: Kyle————————————————-
Sent: Wed, December 06, 2006 8:15 AMYou need help. I’m sorry I offered to help. Yes they will care actually about the other people you just casually dated I was informed as it was a major contributor to my mentality as far as men go. “The Girlâ€?, well, that was the straw that broke it. My friends are wonderful, understanding, and true people. They know who I am as far as what makes me happy truley makes me smile, what makes me sad truley makes me cry, the hobbies I have and the outdoor things I like to do truley are fun to me. “Those are things you do, not who you are. Who you are is just fine” Good luck making yourself better with God but you may want to admit who YOU truley are first to yourself and those you’ve hurt.
You certainly cannot determine the sentence I should serve as you do not know the entire story. Perhaps one day you’ll hear it on TV once I speak and the reporters really investigate. Best of luck to you in all that ensues. Congratulations. The only part of my marriage that was real was my naivety. I thought you’d let “the girlâ€? go and things would be okay. From the moment she told me everything I hated you, I hated what you took from me, I hated the way you punished me and kicked me when I was down and begging you to talk. I punish people who cheat. You cheat on people because you’re evil. There’s a difference.
I’m absolutely allowed to be on the computer, not sure where you’ve gotten that idea from? I don’t particularily care. I heard they are going to interview “your current girlfriend’sâ€? family. I’d appreciate it if they’d not give there thoughts on me as they don’t know the situation either. Thank you. Goodbye.





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Kyle, I’m glad to hear that you did divorce Jessica. I have always wondered since our last conversation if you were ok.
Jess, I’m sure you don’t believe this but my hubby and I do feel bad about the situation you put yourself in. I do wonder though if you were doing this all along while you were cheating on Kyle with my son. And did you care at all about him? Hmm. We, hubby and I, would hate to have to see you in an actual federal penitentury, because we both feel that something horrible must have brought you to this point. You know I always wondered who you really were too while you lived here. Isn’t it a kick in the ass how now you who kept saying “I’m a private person” ends up with their name and business splashed all over the net? Carma.
You’re a really smart girl, that’s the thing. You could have made the money, you didn’t need to go to this extreme. You didn’t need to keep up the millionaire facade. Did you think that was the only way any one would love you?
I would say please do get the help that you are offered, but one has to admit to theirselves that they need the help first. You can change, and you’re so young yet.
Well being one of the prosper lenders who fortunately thought that Jessica was really behind her mothers loan I wont lose when this thief absconds with the money in a federal pen. I certainly hope she gets the full 2 years as she deserves. The exec may be in the wrong to be cheating on his wife with a tramp like Jessica but he CERTAINLY didnt deserve or ask to be extorted. Jessica get used to it. Your husband has outed the rest of your history and your name will be synonymous with the words, extortionist, grifter, scumbag, and SLUT. You ruined your life, not your ex husband, not your mother, it was all YOU. Get over youself girl, You dont have any friends you just have victims.
Jessica,
How skanky can you get? How dare you threaten your ex. You are the nasty hoe that tried to get money from the Pespi man. Your the one that was willing to almost sleep with him to get it. You are the one that tried to get money from all these men on the internet. It was all you.
You really need to stop with the damn self-pity party you are TOO OLD for that shit. ITS ALL YOU YOU DID THIS TO YOURSELF!
Blaming this on anybody else makes you prove your ex right.
You are crazy.
Get help
JESSICA wOLCOTT IS A CLASSIC GRIFTER. SHE IS ALSO A LOSER AND OUT OT MAKE MONEY. SHE IS A MANWHORE. JESSICA WOLCOTT LIKES TO SUCK OFF SHEMALES. SHE IS INSANE.
the federal penitentiary is nowhere for a girl like jess… she has had appartments smaller than her cell will be – and just like the rest of her life, someone else will be footing the bill. i’ve known her for years, and i’m not aware of a single friend that she didnt manipulate or screw over. and yes, its true – she IS a little free with her charm, and very, very uninhibited when it comes to anything that will get her attention. as sad as it is, i honestly believe that there is no help for her. she has no soul.
I have had the unfortunate pleasure of encountering Jessica Wolcott. She came to my hometown of Huntingdon,PA claiming to be wealthy and own a winery. She claimed that she was a medical doctor, and lived in Pittsburg. She is now in a relationship with my ex-boyfriend who is now footing her bills. I tried warning him about her. She was psychotic from the beginning although extremely intelligent. She knows what she wants and she has the intelligence to manipulate until she gets what she wants. Jessica wedged me and my ex of 4 1/2 yrs apart by claiming that I was sending her death threats. When in fact, I honestly believe that she sent them to herself. If investigators could prove the messages came from her own computer I would definately press charges for defamation of character and slander, and any other charges that apply. I feel sorry for my ex because even though all of this evidence is on the internet he chooses to believe Jessica when she tells him that this is all lies. Jessica is a tornado of disaster. Now he is going to reek her havoc. She is well aware of what she is doing and has done to people. She is self-centered and lacks any emotions yet prays on other people’s emotional weaknesses.
Hi,
I read about this item on http://suburbarazzi.com, http://www.craigslist.com and http://www.craigslisthiddencash.com.
What was the outcome of this story? Was Jessica sentenced? For how long, and where? I have contacts who would like to have her appear on about 4 adult magazines doing a photo spread. I can’t mention the ones here due to non-disclosure obligations. If she needs money then this could be useful to her. At least this would be a more honest way of getting money than lying, extorting, or using people. If Jessica is interested in this, she can contact me at jezibelcity@yahoo.com
Antn
She hasn’t been sentenced yet. Her case, like so many, has entered into a protracted kind of legal purgatory. The judge working the case, Colleen McMahon, has since left White Plains, and the new judge, Kenneth M. Karas, hasn’t started yet. It looks like he’ll be up and running by September and then, presumably, Wolcott’s sentencing will be scheduled shortly thereafter.