Reader Emails

Reader Email: I Was Juicin Jeremy’s Cellmate And He Bragged About Conning Rich, Hot Women Into Paying For All His Shit


It’s been almost a month since Juicin Jeremy Winslow was arrested for cocaine possession and driving without a license on the night that he got his girlfriend Tanya Hall killed. But we recently received the following email from his cellmate while Jeremy remained stuck behind bars on $10,000 bail:

I don’t know if you still care or are interested in Jeremy Winslow. If you are message me back. I was just his cellmate at Rockingham. we shared cell B7 while he was on suicide watch and he told me a lot. 

My name’s redacted. From Vinelink you can see we were in at the same time. We were cell mates in cell B7. Where to begin with this weirdo. Before we became cellmates and I even knew about his case my cellmate at the time and I used to watch him on the phone and he’d cry on demand then next second just be fine. Before we heard about case on news we thought he killed her the way he was acting.

He disappeared off the unit and we all assumed bailed until they brought him back and put him with me. He went in suicide watch (he’s told me 3 different reasons why, so I’m unclear on actual reason.) He was never actually or even appeared actually suicidal though. He was a different person inside the cell. Before he was all “crying” and devastated about his ‘fiance’. Then in the cell he tells me about how he actually has been living with his girlfriend Katie for last year and the victim knew nothing about it. He said he was using Katie for her money and she was built like a keg with 2 stick legs under it. She worked as corporate lawyer for Johnson and Johnson and traveled a lot. They lived in South Boston. (A previous arrest comes up when Google his name with the address that matches street he told me they lived on).

She bought him the Jeep that was involved in the shooting and gave him his own Amex card. Said he used it to go to clubs every weekend and fuck everything in site and Max the card out. He is also or was desperately trying to bail out but they want the whole $10k or collateral. He is or was actually trying to get the Jeep title to put up. Was also very concerned more charges were coming and needed bail quick. He said him and (Tanya) Hall fought constantly and broke up every week. He also said his brother was a BRO and he had been in previous confrontations with the leader where he made him look stupid when they wouldn’t fight him. Said he called them out before and they wouldn’t fight him when the leader told his men to do it.

Also after his arrest he said he called Katie and she said she would try to take care of everything for him but had to keep some distance for sake of her job and reputation. Then as later info came out she refused his calls and had her lawyer send his lawyer a letter requesting no contact.

This unrepentant piece of shit.

I’m still in awe that he was able to manipulate all these beautiful, successful women into paying for all his crap. He is the ultimate con-artist, and he clearly feels no remorse if he was gabbing like a school girl in jail. He bragged to a complete stranger that he was using a woman who lives in South Boston while dating Tanya, presumably because gorgeous women can’t resist his hog, and being a mooching loser is something to aspire to.

We checked out his cellmates information and it’s all legit, as is the story of Jeremy’s December 2018 arrest, in which he listed his other girlfriend’s South Boston apartment as his home:

Jeremy Winslow, 407 D St., Boston; operating a motor vehicle with a suspended registration, one-year general continuance, $250 costs; operating an uninsured motor vehicle and unlicensed operation of a motor vehicle, both one-year general continuance (Newburyport).

That’s one of the highest rent districts in Massachusetts, right near the Seaport. Obviously this mistress is successful and well off, and was so enamored with this queef that she paid for him to stay there, and even bought him a Jeep that he never should’ve been able to drive because he’s not licensed.

Hopefully his next mistress is Michelle Carter when she gets out of jail, because this guy’s entire life plan involves conning one successful gorgeous woman after another. He’s already gotten one woman killed in his pursuit of free shit, and he clearly is indifferent and oblivious to the pain he’s caused. Who’s next?


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23 Comment(s)
  • RED
    April 6, 2019 at 7:26 pm

    I hope Juicin’ Jeremy has enough $ in his canteen for KY Gel and some tampons. It doesn’t sound like he is getting out soon!

  • What!?
    April 4, 2019 at 11:04 am

    At least the taxpayers aren’t paying for his free stuff.
    He is in jail paying for what he did, but again, taxpayers are onlly paying for the incarceration and not 5 differnet EBT cards, Section 8, TANF, Mass Health, Obamaphones etc.

  • Jim
    April 4, 2019 at 8:53 am

    “I’m still in awe that he was able to manipulate all these beautiful, successful women into paying for all his crap. He is the ultimate con-artist, ”

    Pro gold digger.That there makes him more qualified to call himself transgendered than Caitlyn or that bank robbing fag lol

  • Time For A Name Change
    April 3, 2019 at 8:16 pm

    “Sloppy Jeremy” is going to be a wide receiver soon.

  • He's Gonna Love It
    April 3, 2019 at 7:06 pm

    Without roids in prison he is going to deflate and DeMarquis and his buddies are going to pull a train on Juicy Jeremy

  • bigdaddy
    John Kerry
    April 3, 2019 at 6:32 pm

    He is giving us gigolos a bad name

  • The angry taint
    the angry taint
    April 3, 2019 at 5:22 pm


  • Ralph
    April 3, 2019 at 5:17 pm

    Juicin Jeremy Winslow you won the coin flip … you can give or receive. Please state your choice!

    • Juicin Jeremy
      April 3, 2019 at 7:11 pm

      Thats obvious Ralphie boy you fishing homo. It will be give. Now get on all fours cause you know you want it bitch.

  • Harry Richard
    April 3, 2019 at 5:13 pm

    Stellar journalism, relying on unverified emails from alleged criminals.

  • David Lee Sloth
    April 3, 2019 at 5:09 pm

    I’m just a gigolo and everywhere i go people know where my farts are spraying

  • LOB
    April 3, 2019 at 4:57 pm

    Juicin Jeremy Winslow may you rot away in prison! ( and become someone’s boyfriend! )

  • Big Wick
    April 3, 2019 at 4:46 pm

    Juicin’ Jeremy, another gift that keeps on giving. Just waiting for the final nail to send him to the Turtleboy Graveyard.

  • Matt Corridori
    Last real reporter
    April 3, 2019 at 4:28 pm

    “We checked out his cellmates information and it’s all legit”. This is what a real journalist does. If someone wants to be an anonymous tipster that’s fine but their story MUST be verified. The mainstream media no longer does this. They just say “an anonymous source said abc”. Turtleboy is our last hope for the truth. Keep up the good work and in the immortal words of President Reagan, “Trust, but VERIFY!”

  • Acquaint Yourself With Your Own Stupidity
    April 3, 2019 at 4:22 pm

    Todays Law Degree isnt worth the paper its printed on.
    Does Katie lack critical thinking skills and good judgement?
    Most schools are diploma factories now.

    • Reel it in Fuckwads
      April 3, 2019 at 5:28 pm

      Katie is good peeps man. You cannot blast her for having a trusting heart. This douche bags scam was good. Like many have said, he’s a con artist. let’s face it, 99 out of 100 guys that are jacked like that are gym rats and usually have some sort of successful life. If you knew Katie, you would say she was anything but a stupid broad. In fact, as the report writes, she’s a smart intelligent woman who’s made good for herself. The katie I know is an incredibly hard worker and the last thing she deserves is to be brow-beated for being scammed by that jack off. I and friends thank the lord it was not her that got caught in the tragedy. I pray for the girl that did lose her life. lets keep the focus on the dirt bag turtle rides. This one’s close to home. Did not Bristol even admit yesterday that she got mixed up in a fupascam? It fucking happens.

      • Bobby Finstock
        April 3, 2019 at 5:50 pm

        Hi Katie. Are you really built like a keg with 2 stick legs?

        • Kegsley
          April 4, 2019 at 8:48 am

          I want to see what a keg on two sticks looks like.

      • Nasty Freak Lawyers Doin it and Doin It And Doin It Well
        April 3, 2019 at 7:22 pm

        Katie gets down on all fours for illiterate roid fresks. Again where is her judgement? It appears as that she thinks with her clitorus instead of her head.

  • Jeremy's Twin Brutha
    April 3, 2019 at 4:11 pm

    Next time I see Katie at Lincoln on West Broadway, I will be sure to hit her up for a few free drinks.

  • Christopher Lettiere
    April 3, 2019 at 4:09 pm

    Maybe, Jeremy and Angela Guerrera should get to know one another…

  • Well, No Shit
    April 3, 2019 at 4:05 pm

    It would be awesome if he pulled a “Hernandez Special” in his cell.

    Fucking scumbag.

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