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Drink about something
EPISODE 97: Abraham Shakespeare
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A $30 million lottery ticket sounds like freedom, until it starts sounding like footsteps behind you. We’re drinking about the true crime case of Abraham Shakespeare, a Florida lottery winner who went from day labor and barbershop hangouts to sudden fame, nonstop handouts, and the kind of attention that turns every relationship into a transaction. We talk through how he took the lump sum, how quickly the money moved through houses, mortgages, and “loans,” and why winning big can make it impossible to know who’s actually in your corner.
Then we dig into the part that still makes our skin crawl: the slow takeover. Dee Dee Moore enters Abraham’s life through promises of help, a book deal, and financial planning, but the red flags stack up fast. We break down the conflicting stories, the strange phone calls, the texts that don’t make sense for an illiterate man, and the shifting explanations meant to keep police and family at bay. The investigation turns into an undercover operation, and what comes out is one of the most unsettling “jackpot murder” cases we’ve covered.
You’ll leave with more than a timeline. We get into real-world lessons about lottery privacy laws, anonymity, boundaries, power of attorney, trusts, and why giving publicly can invite the worst people to test your limits. If this story hits you, share it with someone who still says “I’d tell everyone if I won.” Subscribe, leave a review, and tell us your rule for handling sudden wealth.
CHECK OUT THE BAND!
https://www.youtube.com/watch?v=kEOLzMWN2AM
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AS ALWAYS D-A-S
Hey Jesse. Hey Lindsay. What are three things that you would do with your money if you won the lottery?
SPEAKER_00Oh my God. I would probably take a sweet ass vacation and put a shitload in the bank and then retire early.
SPEAKER_03Okay. I would, of course, make sure our family is well off, donate to women and children's shelters, and then invest so that everybody in our family on down is set for life.
SPEAKER_00Hell yeah. And I'm gonna drink a whole shitload while I'm doing it. So happy Friday, everybody.
unknownYes.
SPEAKER_00Yeah, yeah. We've won the lottery. The lottery on a Friday.
SPEAKER_03Happy Friday, everybody.
SPEAKER_00I don't know if I'm overspeaking, but a lot of people do fuck away a lot of their lottery money, you know?
SPEAKER_03Oh yeah. We're gonna talk about it a little bit today.
SPEAKER_00Oh.
SPEAKER_03But first, I want to ask you what made you feel old this week. Oh, wait, first. What are you having to drink today?
SPEAKER_00You're firing so many questions at me, and I'm not ready. I just want to be drunk and over here, quiet. No, I'm not even drinking anything hard. I got this uh the energy drink mixed with a um white claw that you got me in the fridge over there. And that's just what I put together. I don't fucking remember which one it was. I poured it together and I'm just hanging out and banging out and doing whatever I do. What are you drinking over there?
SPEAKER_03I've got a double raspberry vista bay. No energy drink. Because earlier I drank um, so it's Aldi's version of like, I don't know if it's Aldi's version of an Alani or a Celsius. I don't know. But it was orange cream sickle and it was delicious, and it was only 70 grams of caffeine opposed to 200, but it had me wired a little bit more than the other drinks.
SPEAKER_00So you kind of geeking a little bit. I'm a little wide open over there.
SPEAKER_03I mean, I'm always wide open, but it was like, I don't know, it was a different type of energy. I'm not really sure if I'm a fan. But anyway, so what made you feel old this week?
SPEAKER_00I was looking at some videos that people tag me in from like 20 years ago and how cheesy I was. And that made me feel old. And then I've seen all the comments behind it. It made me feel old as fuck.
SPEAKER_03Well, I think we all have moments that we look back on, I do daily, be like, God damn, I was such a dork. Why do people like me? But maybe that's what they like about me, is that I'm a dork. And I just had to, you know, deal with that. But I I had something else in mind, but then another occurrence happened. So our dryer went out. We had to wait on an element to come in to replace. So I did my drying of my laundry at my bestie's house. And I'm a server at a restaurant. And when I was folding my aprons, I remember 20 years ago, my best friend that was working at the restaurant that I work at at the same time. She taught me how to put the crease in them without having to iron it. And I was doing that while I was at her house. And it just made me think of that. And it was like, how the fuck is that 20 years ago?
SPEAKER_00Oh, you learned that 20 years ago. That little trick.
SPEAKER_03And I'm just still doing it. And I was at her house. Like it's it's it's fucking weird. It's came full sun.
SPEAKER_00Lindsay, I probably have work uniforms that are 20 years old.
SPEAKER_03Oh, I do. I mean, no, I don't have no, you don't. No, you don't.
SPEAKER_00Jesse, your uniforms are completely death shrouds for at least 15 years. Okay.
SPEAKER_03No, your work uniforms were completely different when you and I met. You had khakis and polos, and you had blue pants and blue shirts, and now you have all black.
SPEAKER_00I feel like I've been wearing the Johnny Cash uniform for 20 fucking years.
SPEAKER_03I wish I could wear all black. I wish I could.
SPEAKER_00I'm trading my shit in, dude. I'm gonna get like a like a tuxedo. Just wear a black tuxedo to work.
SPEAKER_03Every girl crazy about our soft drills, man.
SPEAKER_00Oh, the drummer just died.
SPEAKER_03I was about to say I heard that yesterday. But they've been old our whole life.
SPEAKER_00They've been old our whole life.
SPEAKER_03Oh, yeah, they've been old our whole life. Do you remember the ZZ Top Muppets on Sesame Street? Yeah. Oh my god, they were the greatest. And it was crazy because I get in the car last night, and my my radio is always set at either liquid metal or octane. And it was on liquid metal when I got in, and liquid metal was playing ZZ Top. And I was like, what the fuck? And I was like, oh, that's why.
SPEAKER_00Yeah.
SPEAKER_03Rest in peace.
SPEAKER_00They had the coolest fucking car ever.
SPEAKER_03Yeah.
SPEAKER_00Well, they didn't have a lot of people. They did a good Super Bowl show. I thought they did a really good halftime show. I thought, I mean, I don't know. What's your favorite your favorite halftime show at Super Bowl?
SPEAKER_03That in my lifetime that I can remember.
SPEAKER_00Yeah, that counts.
SPEAKER_03Prince.
SPEAKER_00Mine. Fucking two Lindsay. What year was that? I don't remember. But I wish they'd have had it every year. Yeah. And it rained during it. Two fuck. That was the coolest fucking show. Let me play this guitar. And he just fucking rocked it out and it was out of tune. He was playing it live and he still played it perfect. Because it's Prince. How do you pick up a guitar that's out of tune and still rest in peace? Adjust in the middle of that and then play it perfectly.
SPEAKER_03Because he's Prince.
SPEAKER_00Oh.
SPEAKER_03And then he was the artist formerly known as.
SPEAKER_00I mean, okay. I give all the love to Prince. Like he was on stage with those dudes one time, and there was, I don't I don't forget, it was like an award show, and like everybody was up there playing guitar, and he just blowed it up and then threw the guitar.
SPEAKER_03You know what? The internet also says that it was the greatest halftime show in NFL history, and it was in 2007.
SPEAKER_00There you go. Yeah. There you go. Let us know if you concur. Yeah. Yeah, if you concur.
SPEAKER_03And I didn't even do the introduction. Welcome everybody. This is the Drink About Something podcast where we talk about true crime. We have a couple of drinks. And at the end of the episode, Jesse plays a couple, or not a couple of bands, but he plays one band. While we have a couple of drinks.
SPEAKER_00We talk about many bands all the time.
SPEAKER_03Oh, all the time. There's at least three mentioned. So here we go. We're gonna get to the story. Uh we're today. We're drinking about Abraham Shakespeare.
SPEAKER_00Is he kin to uh William? Or no?
SPEAKER_03I don't know, but I don't think so. But you never know. You really just never know.
SPEAKER_00It's a badass name. It is. That's almost like a Luke Skywalker type name.
SPEAKER_03Yeah, the Abraham motherfucking Shakespeare.
SPEAKER_00You gotta put all that with it, right?
SPEAKER_03From the mountains of Caucasus. No, he was not from the mountains of Caucasus.
SPEAKER_00Oh, well fuck. Well be damned. I didn't know. I'm I don't know. Whatever the From the Hills Have Eyes.
SPEAKER_03Well, Abraham Shakespeare was uh Shakespeare. Shakespeare was, he was a black man. Uh he was born April 24th, 1966, in Sebring, Florida. I got family in Seabring, to Elizabeth Walker and his father, which I could not find a name for. But it is said that he was close with both, with both of his parents. He had a brother named Robert Brown and a sister named Lynette Williams. He grew up living between Lakeland and Lake Wells. Got a lot of family in Lakeland. And he struggled really hard in school, never really learning how to read or write. And in the seventh grade, he dropped out and would go on to work with his dad in the Orange Groves. Now, it was said that he actually dropped out to help support the family so his younger siblings would be able to continue their education. Unfortunately, he started getting in trouble when he was just 13 and he would be convicted of theft and sent to a juvenile program where he would remain until he was 18. When he got out of the program, he moved in with uh back in with his dad. Okay, I'm sorry. Some sources say his dad, some sources say his mom. So I'm gonna say it several times in this. All the evidence out there and all the research out there about this case is it contradicts itself a little bit, but I did the best that I could. So he goes and he starts doing like day labor jobs, and he would hang out at his friend Greg's. Uh, or actually, Greg became his friend later on. So he was hanging out at this barber shop, and Greg owned the barbershop. Abraham would be like kind of out there asking for money, and Greg was like, Hey, I don't want you out here begging. How about I give you some work to do? So he would sweep and take out the trash and do stuff like that. Like, and then Greg said that he made the barbershop become an actual barbershop. Like a little Adam Sandler there. Hell yeah.
SPEAKER_00Make you silky smooth.
SPEAKER_03Yeah. So he would help Greg out during the day and hang out with the fellas and the barbershop. And that was just like that was his day-to-day for a while. And then he got a job as a trucker's assistant because he, I don't know if he could not or would not get a driver's license. I'm really not sure. But it could have been because he was illiterate.
SPEAKER_00In fear of. Yes. Yeah.
SPEAKER_03That he didn't get the driver's license. So he would be the right-along to help unload the trucks and uh when they would make the deliveries. He would go on to father two kids by two different mothers, and their names were Moses and Jeremiah.
SPEAKER_00So here we are. Now Father Abraham.
unknownYeah.
SPEAKER_03Oh shit. Yeah. Yeah. I had to go there, Lindsay. How many sons? Okay. Sorry. I went right back to childhood where I was marching and shit in place at church in Sunday school singing that shit. Ugh.
SPEAKER_00Ugh. You look at all the mechanics of that song, and it's kind of fucking disgusting.
SPEAKER_03Right arm. Left arm. I don't remember the whole thing, but I remember marching and singing the song. That was my favorite part. Oh my God.
SPEAKER_00I could not wait to turn around and sit down.
SPEAKER_03Now, like I said, I'm going to say it many times. I heard from some sources that he was a great father, and some sources that he was not. Jesse's stuck. Still singing the song, Lindsay.
SPEAKER_00Nod your head.
SPEAKER_03If you know that one. Oh my God. I'm going to have to look that shit up later.
SPEAKER_00No, I don't want to remember it. I don't remember it. We're going to play it all day. All day tomorrow. That's your weekend song, Lindsay.
SPEAKER_03But all sources say that he would get behind in child support payments. Yet he was always buying lottery tickets. Now I don't know if $5 here or there, or even $5 a day, doesn't really add up to a child support payment, but you gotta have your priorities in order, okay? Yeah. He did go to jail for a few days when he was a certain amount past due, and he would pay the balance required to get out of jail and go on about life. You know, that's how I after about year four, maybe five, after my divorce from my ex-husband, that would be the only time I would get paid was when he would go to jail for being behind.
SPEAKER_00Dude, shit.
SPEAKER_03I know. But you know what? I would never know. It would be a surprise. It would hit my account, and I'd be like, hey, okay. Hallelujah. Hallelujah.
SPEAKER_00We're goof fooding. I'm still stuck. You don't know. I think you know.
SPEAKER_03Get Father Abraham out of your head.
SPEAKER_00I can't. I can't. Leave me alone.
SPEAKER_03It is said by most that he was a positive, helpful guy who would do anything he could just to help someone out. When he was 41, living with his mom in Lakeland, he was on a route to Miami with his driver, Michael Ford, and they stopped at a gas station. He asked Mike if he would buy him a few lottery quick picks, and Michael did, and they went on about their day. Now, here again. One source said that he was in the store, Abraham himself, and he bought two and he wanted to buy one more. He borrowed a dollar from Michael. Michael gave him the dollar and he got the third one from that dollar Michael had. Most, all the other sources, like six other sources, say that Michael went into the store, bought the tickets. When he came back to the truck, Abraham gave him two five dollar bills. So I'm gonna say that that is the correct story because more than one said that, and only one said that he borrowed the dollar from Michael. Okay.
SPEAKER_00And it's so specific. I mean, that makes it makes sense that way.
SPEAKER_03Right. So later on, when those winning lottery numbers came on the news, Jesse, give me the lottery number beat. And you know which one I'm talking about. Twelve six. Twelve.
SPEAKER_00Oh yeah.
SPEAKER_03Fifty-two. No, it's like I know I'm not. Okay. 45, 37. In this case, 42, 52. Abraham could not believe his eyes.
SPEAKER_00That's because I like potato chip.
SPEAKER_03These were his numbers. He had won thirty million dollars.
SPEAKER_00Dollars. Dollars. Dollars. Dollars. A dollar, bro. A dollar, bud.
SPEAKER_03Now he decided to take the lump sum instead of getting monthly payments. Which after taxes and penalties, because you get a penalty for getting that. No. No. You're gonna shit. So you get a penalty when you take the lump sum. So you gotta pay the taxes. And then if you get a lump sum, you pay another penalty. And after all that was paid, he got 12.7.
SPEAKER_00For fuck's sake, the dream has gone away. See, that's why I said I would go to fuck off. I would go just fuck back home.
SPEAKER_03A life-changing amount of money.
SPEAKER_00It's silly. Nah. I would get a retire like at normal retire age.
SPEAKER_03But you gotta remember this was 2006 before inflation was disgusting. Okay. So if you take the payments, it's actually a better option if you're not uh if you're not educated. Because if you don't know how to invest the money, those yearly payments actually accrue interest. So you get more once it's all said and done. Now, you may not live to see all of that money, but your family will continue to get it.
SPEAKER_00If you play the cards right, you still have to get beneficiaries and everything set up right. Otherwise, they're gonna take it too.
SPEAKER_03Right. I mean, yes. So he got the lump sum, he paid off his child support debts and set up a trust for his son Moses in the amount of $1 million. Jeremiah wasn't born yet. He bought his mom a house, he bought his cousin Cedric a house, he gave his stepdad and his stepsisters money. Uh, he gave his stepdad a million dollars and all three of his stepsisters $250,000 each. He paid mortgages for other friends. Um, he bought, he paid a mortgage for a neighbor and some guy who he didn't even know the last name of. It's said in the documentary that I watched that I'll plug later on, that it wasn't just him that won the lottery, the community did.
SPEAKER_00So he done spent about $9 million already.
SPEAKER_03And then it just seemed like everybody had their handout. He was buying houses for people as like he was the bank, and they were taking out a loan from him, and he was paying them the monthly payments instead of the bank. He did buy himself a $1 million home in a gator community in North Lakeland, and this was about 15 minutes from his mom, and he bought a couple of cars, even though he can drive. I mean, oh no, you know, it's the thing. You know that Cardi B, she did the same thing. She bought a shit ton of cars. Don't got Naralasia. Narrow last at all. Yeah. But you know what? I I guess if you can do it, do it. Now, after he has, you know, some, you know, he's he's having fun with his money. He's having some parties. And he met his girlfriend or his his next girlfriend at one of those parties. And she became pregnant with his second son, who would be Jeremiah. Now she would later move out because she really didn't like how he was constantly hounded for money and not really saying no. Like she didn't want it all to be spent on her. She just wanted it him to be smart about it, you know? And after a while, he tried to stay hidden, but people were constantly coming and asking him for money. And he even bought a doormat that said, go away. I would too. You know, I didn't even look it up and I meant to. Like I had it on my brain all week. But there are some states, I don't know if it in Florida, because that's where he's, you know, Lakeland, right down the road, two and a half hour drive. I don't know if you can get your money anonymously here. But there are some states where you can't at all. You can you can here? Yes. Okay.
SPEAKER_00And that would be how I did it. I mean, nobody would know. Nobody would just nobody would know. And at least 90% of that shit would be in a bank. I wouldn't even fuck with I would fuck with 10%.
SPEAKER_03We would have that 12-foot skeleton from Home Depot.
SPEAKER_00Like that $300 skeleton sitting out there. Fuck yeah. Maybe even two or three of them. Fuck it.
SPEAKER_03And I would probably have those dance witches too. Yeah. Have you seen them where they've got Marlon and Damon from um White Chicks going, oh, you want to talk about mothers on White Chicks? Mothers. Where they do the mama jokes.
SPEAKER_00Yeah, yeah, yeah, yeah.
SPEAKER_03But like the witches are moving like that. It goes perfectly. You gotta get up on the TikTok, Jesse. Jesus.
SPEAKER_00I don't know. I just I don't know.
SPEAKER_03Michael Ford, the man who got him the tickets, he figured he was entitled to some of that money. And in fact, he wanted half. And he just hey, oh my god, stop it.
SPEAKER_00Haif and half.
SPEAKER_03And he decided to sue Abraham and say that Abe had actually stolen the ticket out of his wallet. Come on, Michael. You know better than that.
SPEAKER_00Poor little Michael. Aw.
SPEAKER_03But Abraham literally came to court with a garbage bag full of old tickets to prove that he had been playing the lottery for a long ass time. And this won him the case. So before court, Abraham had offered him 250,000, and Michael was like, no, I went half. So Michael lost all, I mean, like, he didn't even get the option anymore to get the 250k. What an idiot.
unknownYeah.
SPEAKER_00I would have took it. Yeah.
SPEAKER_03I would have been like, all right. Thanks, man. Thank you.
SPEAKER_00Cool. You gave me my dollar back in the worst case scenario, at least. Right. Sounds too much.
SPEAKER_03Well, like I said, only one source said that.
SPEAKER_00$89.99.
SPEAKER_03Only one source said that. Many, many, many others said that Michael buy him the tickets and Abraham paid him for them as soon as he got back in the truck. You know? Well, Abraham grew tired of his lottery fame. And even though people were around him all the time, he didn't feel like any of these people were his friends. In fact, he told a reporter later on that he wished he could just go back to life before he had won or just disappear altogether. And he did. In April of 2009, no, excuse me, November of 2009, it started to dawn on a few that they hadn't seen him since April of 2009. Seven months. He had stopped going to the barber shop and to the store that his best friend named Eddie Dixon ran. And these were his two. Hangouts. So his cousin Cedric decided to report him missing after seven months. And I think this was just because he couldn't find him because Cedric was having money problems. Cedric reported him missing and said, Hey, I hadn't physically seen him since April.
SPEAKER_00So they all really cared. He gave him so much, but they didn't give a fuck about him for seven months.
SPEAKER_03Now, Sheriff Grady Judd and Detective David Wallace started to question Abraham, everyone that Abraham knew. Eddie Dixon said that there was a woman named Dee Dee Moore who they needed to talk to. Now, Abraham had met Dee Dee Moore through his realtor, Barbara Jackson, and Dee Dee told Abraham that she would like to write a book about him. And then she also became his financial planner. Now, Dee Dee, she had been a part of a few insurance and medical scams in the past. One where she even made it look like she had been robbed, kidnapped, and gang raped by what she described as Latino men.
SPEAKER_00So here we go. Salad time.
SPEAKER_03And when Barbara Jackson had met her, she was in a wheelchair from a supposed car accident. But then two weeks later pulls up to Abraham's house and is wearing high heels.
SPEAKER_00It's a miracle.
SPEAKER_03It's a fucking miracle. Now she talked Abraham into letting her be his financial planner because she had actually written a book about financial advice. And a man who was pretty much illiterate and had taken on a lot of money and receiving multiple mortgage and loan payments, he needed some help because he was down to just $2 million by 2009.
SPEAKER_00What did I say earlier?
SPEAKER_03$9 million gone. And DD, she ended up even moving in his house. She purchased his house from him for about $400,000 less than he had paid for it and became the manager of his LLC for all the loans in real estate. And then she became like the power of attorney for the rest of his money. Yeah. She's taken Instagram photos or posting Instagram photos of her at his pool and things like that. And she had a boyfriend. Like this was not a romantic thing between the two of them. She just now controlled all of his assets.
SPEAKER_00But she was locked on target.
SPEAKER_03So after he is reported missing, Didi, she starts to get word of this. And then she starts getting questioned about this. And she decides to take his mother out to dinner at Cracker Barrel to assure her that Abraham was just fine. And he just wanted to be left alone. And Abraham just happened to call Dee Dee while they were having dinner. And she passed the phone to Elizabeth. And on the phone, Abraham said, Mom, I'm fine. I just need some time to myself, or something along those lines. I'm not sure what the exact conversation was. But Elizabeth wasn't convinced. And she was like, I don't really think that that was my son. And Dee Dee was like, oh, he's just sick, girl. He sounds a little different. But Elizabeth still made sure that the investigation continued and missing persons' photos went up with a very meager reward of either, I've heard both, $5,000 or $10,000. This is a man who gave millions to the community. We couldn't do a little better than that.
SPEAKER_00No, they don't give a shit. They just want to do that.
SPEAKER_03They're like, okay, Abraham, if you they put it out, you know, in the media, widespread. If you don't want to be found, that's fine. But just contact us. Let us know that you're okay.
SPEAKER_00That way we can quit.
SPEAKER_03That way we can close this investigation. But they never got any word from Abraham. So investigators in the media, they're hounding Didi because she was the last person to see him. And she was the one that was telling everybody that he wanted to disappear. At first, she said that he was dating a Jamaican woman and they were going to go live in Jamaica with her and her family. Then she said that he had contracted AIDS and went to go somewhere to die in peace.
SPEAKER_00Which is like all over the fucking place. Yeah, it's this is not.
SPEAKER_03I mean, first of all, he's got, I mean, he's only got two million left, but he's got money. He could get treatment. And this was, you know, 2009. We're way past the 90s where the stigma is terrible. Yeah, they had a pill now. Contract AIDS. You contract HIV, which develops into AIDS after a long period of time. You don't just, it don't just go full-blown. AIDS.
SPEAKER_00They had a pill now. You can just take a pill once a month. And now they got one you can take like twice a year.
SPEAKER_03Right. Things aren't adding up, Didi. Then she said that there was video evidence of him having relations with an underage girl and that he was running away from potential jail time. Then she would say that he was running away from custody battles and avoiding child support, which made no sense because he was seeing his kids previously, and he had, in fact, paid all of his child support debts up to date. Now, I don't know about ongoing, but all the rears that was paid for. And more, I'm sure. Exactly. And he had the million-dollar trust set up in Moses' name, and Jeremiah was only like a little teeny tiny baby at this point.
SPEAKER_00It sounds like she is just right on target. Mm-hmm.
SPEAKER_03Now she eventually would say, Hey, I'll set up an interview with him. But all she came up with was a recording that she had of him saying that he did, in fact, want to disappear. And this was on video. Uh, she asked him where he wanted to go, and he said pretty much anywhere, he wasn't really a picky person. But then he gets really irritated with her and he asks her to stop recording.
SPEAKER_00I was hoping that it would be like a weekend at Bernie's type scenario. Oh God.
SPEAKER_03That's crazy. Now she would later say that she made this video because she had already known that she would become a suspect. That's also red flag.
SPEAKER_00There, gotch.
SPEAKER_03All of her conversations with the investigators and the media, they would end up in tears. Like she was a really concerned friend. But investigators, they were not deterred by the tears. They smelled something foul, like foul play. They searched the house, they searched her phone, her computers. They even gave her a lie detector test. And the only thing that they found, and this was really odd, was that when Abraham, in quotations, had called when they were at the cracker barrel, the phone he supposedly called from had pinged off the same tower as Dee Dee's. So that would mean he would have been close by. And then also Elizabeth saying that she was definitely not convinced that that was her son. And it wasn't. After Abraham supposedly disappeared at his own free will, Dee Dee contacted Greg Smith, the one who owned the barber shop. Now, Greg Smith owed him $63,000 because Abraham had paid off the mortgage on his bar. I don't know if it was on his house or on his shop, somewhere along those lines.
SPEAKER_00He's setting everybody up hoping they would get the money to come back to him. Yeah.
SPEAKER_03Now Dee Dee tells Greg that she will dismiss this loan because now she is in charge of all that. She is in charge of all the loan payments. So she tells Greg that she will dismiss his loan if he will just call Elizabeth and pretend to be Abraham. And she also says, I also need you to tell anyone else that asks that you have actually seen Abraham. You have laid eyes on him, but he just doesn't want to see anyone else. And Greg agreed. He sincerely thought that Abraham just wanted to be left alone and was like, hey, he didn't have to pay back the $63,000. Now after he made the call, because he didn't know that she was being investigated or that Dee Dee was being investigated, he was picked up by the police and questioned as to why he did it. And he told him. He was like, She asked me to for Abraham.
SPEAKER_00Yeah, he still thought he was being honest throughout all of it. Yeah.
SPEAKER_03So now they really believe that Dee Dee has done something with or to Abraham. Another thing that was really suspicious was that Abraham had been sending texts to other friends and his baby mama. But that was really strange because remember, Abraham is illiterate and had always just called when he wanted to reach out. Oh he was not a texter. So investigators come up with a plan. They're going to use Greg, who Dee Dee trusts, to get more information. So they wire him up and they had him meet up with Dee Dee, who was still asking him to do certain things to keep the heat off of her. One of them being to send a birthday card to Elizabeth from Abraham. Remember, he couldn't read, he couldn't write. And then had Greg call a supposed friend of Abraham's to pretend to be a drug dealer from Miami named Ronald and say, Hey, I just saw Abraham. Tell everyone. He's in Miami. He's good. Now after this, Dee Dee had gotten really comfortable with Greg and said, I need you to do something else for me, Greg. Something big. I need you to help me move Abraham's body. Oh yeah.
SPEAKER_00She had him froze up, probably.
SPEAKER_03Now, I did not write this down, so this is off the dome. Here I go. The police are listening, investigators are listening. They hear this and they're like, okay, we need you to tell her that you've got this friend that is going to take the fall for this murder. The friend is actually going to be an undercover cop, but they're going to tell Dee Dee that it's somebody that's already going away for 25 years. So he's going to take the fall for the murder to get her to admit to it. Okay. This is, like I said, an undercover cop, but Greg introduces this guy to Dee Dee as his cousin Mike. Let's continue.
SPEAKER_00No, I'm just like, I'm looking at you, I'm like, here we go. And the whole twist and turns of everything, I was just trying to figure out because I figured we were thinking of fucking twist and turn, and now we're twisting and turning. Yeah.
SPEAKER_03Now she had already forgotten that she had Greg himself pretend to be this guy named Ronald. And she told him that Ronald was actually the one that killed Abraham, so that he could rob him and had threatened to kill her son if she didn't help hide the body.
SPEAKER_00So she said that he, as him, did it.
unknownRight.
SPEAKER_00But he was pretending to be Ronald, his own self.
SPEAKER_03Yeah, she forgot that she had had him to do that. Right. Yeah. And Greg at this point is mystified, I guess is the word you would want to say, because he had honestly thought that Abraham was alive up until this point.
SPEAKER_00And then here we go.
SPEAKER_03Yeah.
SPEAKER_00And then now I'm also Ronald, and now I did it.
SPEAKER_03Right. Now he had just thought that he was helping with Abraham's disappearance act, okay? So this is when the whole my cousin Mike will take the fall for this. That's when all of this comes into play, okay? So now he's got to go along with all of this. For one, he's being, you know, he's he's he's with the police now. And he didn't want to be killed by Didi either, you know. So he's fucking scared. I would hate to be Greg in this situation.
SPEAKER_00You don't know what she's capable of. Obviously, she's capable of doing a good job at it because she's gotten away with it for this long.
SPEAKER_03So Greg and Cousin Mike, in air quotations, the undercover cop, they go to a property in Plant City that Dee Dee owned. And she told them that Abraham was buried there. Oh shit. Yeah. So cousin Mike, aka the undercover cop, says, Okay, you know, we're gonna help get rid of this body, but you got to tell me where it's at. And they handed her like an iron bar and said, Go place this where the body is. She takes it over to a small patch of land that is covered by concrete and sets it right there and said, He's here. And she handed over the murder weapon, which was a Smith and Wesson revolver. I'm fucking, I'm like, what the fuck?
SPEAKER_00And then she poured concrete over it.
SPEAKER_03Okay, so it is said in several sources. Like I said, a lot of these sources are conflicting. So it is said in one no multiple sources that she called her ex-husband. She's got a boyfriend, by the way. They're all living over at Abraham's house. She called her ex-husband who had a backhoe to come dig this hole. And said that she had asked him to do this many times before. So she's racked up, she's racking them up. No, I don't this Abraham, spoiler, will be the only murder that she's charged for. But why is she asking you to backhoe all these holes? And then she had a concrete finisher come in and fill the concrete. Yeah. Wow. Yeah.
SPEAKER_00Wouldn't that suck to be that guy? And not know it. She's like, all right, I'm gonna go lay this slag.
SPEAKER_03Backhoe holes for your ex-wife.
SPEAKER_00She is that manipulative. I guess. Yeah, she's playing with it. Yeah, she's playing with it, dude. She is on target the whole time.
SPEAKER_03Now, Didi was later seen that night, the night that she placed the iron bar where Abraham's body was. She was seen at Walmart buying digging tools. Because, like I said, Abraham's body was just not underground. It was under concrete. So how the fuck are you gonna I mean, you know.
SPEAKER_00Jackhammer. Jackhammer.
SPEAKER_03In the middle of the night, because that's what Mike and Greg said. Okay, we're gonna have to do this in the middle of the night. You're gonna jackhammer concrete. I don't I don't know how they did it, but they did. All this information was recorded, and on January 27th, 2010, he'd been missing since April of 2009. Detective Wallace and team, an undercover cop, they came and they found it took them two days to find the body of Abraham Shakespeare. Wow. He had been killed by gunshots from the Smith Wesson too. And they found that he had either died the day of or the day after Dee Dee had recorded that video of him because he was wearing the same clothes. Wow.
SPEAKER_00Yeah. Shit. Yeah, she lured him up.
SPEAKER_03Oh god, this sadness just hit me so hard.
SPEAKER_00Yeah, because he has been. Okay, he's had problems and he didn't work out in regular cookie cutter life, won the lottery, and then gave it all to anyone.
SPEAKER_03People he didn't even know. He was paying for funerals because life insurance wouldn't cover the shit, man. It just besides just hit me, y'all. I get it.
SPEAKER_00Well, everyone around him just did, and nobody cared. So that is why you don't do that. Because nobody cares.
SPEAKER_03That's why it should all be anonymous. Anytime you get some money, nobody should know about it. Well, Dee Dee was arrested. But she kept on saying that it was this made-up drug dealer named Ronald. And she also actually blamed her son.
SPEAKER_00Really? She just didn't care. Then she was. She was just destructive. A path of fucking destructive.
SPEAKER_03She blame your show. I think he was 14.
SPEAKER_00And then dragging X's and everybody in.
SPEAKER_0314?
SPEAKER_00Come on, man.
SPEAKER_03Um, and then she said, you know, why aren't y'all looking at all the other people that owed him money? And they did actually go and look at Michael Ford, but he was in Georgia. She gave him the murder weapon and poured it right out where.
SPEAKER_00You can't talk no more, Dee Dee. Oh, God. You can't talk no more.
SPEAKER_03That's what got me. And it's like, she kept all these people. And they told her, bitch, we got you on. I mean, I'm holding up paper, but we got you on this device saying this shit.
SPEAKER_00I would not even, I wouldn't even entertain that fucking conversation if I was the prosecution. I would be like, she could shut the fuck up right now.
SPEAKER_03But they do, they do go and I mean they say they talk to Michael and they find his truck driving records because he's still a truck driver. But all his uh truck driving routes, they cleared him.
SPEAKER_00Yeah, he was busy working, yeah.
SPEAKER_03Yeah. I guess he had just, you know, he had probably just ran away with his tail between his legs. You know, he should have took that 250 that Abraham offered him instead of trying to sue him where he wasn't granted anything.
SPEAKER_00Yeah, had no fucking altar motive other than what pissed me off was he took a chance to get a chance to get jumping in there to try to take his money and took him out and was.
SPEAKER_03He tried to accuse Abraham of stealing the ticket from him. No, sir. And that's why Abraham brought the garbage bag full of lottery tickets.
SPEAKER_00Yeah, well, I mean that was, yeah, that don't even fucking matter.
SPEAKER_03But that's funny to me that Abraham has kept every single lottery ticket that he's ever purchased.
SPEAKER_00Yeah.
SPEAKER_03That's crazy.
SPEAKER_00But he had a golden ticket.
SPEAKER_03He did. Shit. Very unlucky numbers for him.
SPEAKER_00Oh. Unfortunately. He just did not have any. Nobody could be like, hey, dude, listen, I know you got your 12 million dollars. Was it 12 million, right?
SPEAKER_0312.7. Yep.
SPEAKER_00I know you got your 12 million. Here's what you need to do with this. Do this this way, because nobody gives a fuck if you hand out millions of dollars to everyone else. They don't care. They just, they was, they was just fucking happy unless they wanted to come back for some more money. That's the only reason why even this even happened. Otherwise, she would have kept on riding this wave.
SPEAKER_03You know, I I did not hear in any of the sources that I used that she had saw that interview where he said he wished he could go back to his life because it feels like that was her moment. That was where she was like, I need to get into this man's life and figure out how to take all his money because he wants to disappear anyway. I definitely make him disappear. You know what I mean?
SPEAKER_00All that was really his ultimate depression, too, through all that because he just kept on trying to give to get happiness.
SPEAKER_03It was.
SPEAKER_00Yeah. And that's why you don't pay to play, man. No, you let people come and play on their own dollar.
SPEAKER_03Right.
SPEAKER_00Yeah.
SPEAKER_03Now, Dee Dee, she would plead not guilty to her murder charge and say that she had been framed. But the police and prosecution, they already knew that she had previous money problems. She was a scam artist, and Abraham had just been her next victim. And all the recorded conversations between her and Greg, those were played in open court. And even like, so I told you that she had been flirty with a cop. Like she offered to, she said that she had a free room at the hard rock and that she would do things to him. Oh, any means necessary. And that man got right on the stand and said, This bitch tried to F me.
SPEAKER_00Yeah. You know what I mean? Well, yeah. Any means necessary. She was trying to manipulate, and that's why the ex was still hanging out digging fucking holes in the ground.
SPEAKER_03Probably. Yeah. And the jury didn't take long uh to deliberate. They actually took only like three hours, and they said guilty of murder in the first degree, and she was sentenced to life without parole in 2012. She still insists on her innocence and has appealed her case, saying that her case wasn't handled properly, and that she's a great person, and she just loves Disney. That's literally in one of her interviews. And she also says in one of her interviews that anybody that thinks she's guilty is ignorant, like with her full chest.
SPEAKER_00But she actually produced the murder weapon and said she did it, and the location.
SPEAKER_03Yeah, I mean she didn't say she did it, but she provided the location of the body. Yeah. Now uh one of the documentaries that I watched was from the Web of Death series on Hulu called uh Jackpot Murder. And there are many other things on YouTube. Like I said, I've said it a few times in this episode. Everything that I watched and listened to has conflicting stories on Abraham's background and a few of the details along the way. So I did the best I could with the information that was out there. There is also an episode of Snapped about this case. 20 did a special on it called Unlucky Numbers. I mean, there's there's actually a lot, a lot of uh material that you can watch about this case. But Abraham was laid to rest after his remains were found, and it was a beautiful funeral. His boy Moses, who was eight at that time, he got up and he spoke to everybody, and it was just it's really fucking sad. And it's really sad. Yeah. Because this all happened in a matter of three years. Three years. Because honestly, like with other than the trust that was set up in Moses' name, he pretty much died penniless because everything was in Dee Dee's name. Everything had been moved to her thing, which was called it was some like scam thing, also called like medical management bullshit or whatever. And then she had created the Abraham Shakespeare LLC, but she had control of all of that, so she took everything from him. Fucking hell. Now I do believe that the family got a really good lawyer to help them recoup a lot of those assets.
SPEAKER_00Yeah, to pull it back out. Right. Yeah. But goodness gracious. Do not let anyone know if you win a big lump son of money. Definitely never tried.
SPEAKER_03I mean, this all ha this all happened to him after he met Didi within a few months. She took everything from him and took him out. And still swears that she's innocent. To this day. And that has been What was 2012? How long have we been together? Almost 15 years.
SPEAKER_00Shit. Not worth it.
SPEAKER_03No. No. Don't tell nobody about your money.
SPEAKER_00No.
SPEAKER_03Give anonymously if you want to give. Because I'm a giver. I am a giver. Give anonymously at all times. As much as you can. Don't try to get that clout for it. Because by God, that'll take you down. Give anonymously. If that's in your heart, make sure your family is set up. Always. Number one. And then if you want to give it the rest away, do it. Just do it anonymously. That way nobody can hound you for anything. They will know it was you. Period.
SPEAKER_00Yeah. Because what you thought were friends and family was nothing. Nothing. They didn't care about it.
SPEAKER_03Seven months, Jesse.
SPEAKER_00They didn't care. Unless they wanted more money.
SPEAKER_03And I don't want to be shitty, but even his own mama. You know?
SPEAKER_00That's what I'm saying.
SPEAKER_03Yeah.
SPEAKER_00Yeah. Destruction. Destruction.
SPEAKER_03I'm thirsty. I'm gonna get a refill. And while I'm getting a refill, Jesse is going to plug this amazing band that he is about to play to cleanse our palate of this terrible story.
SPEAKER_00I need like three bands after this. I've been kind of quiet over here because it's disgusting. I know.
SPEAKER_01Ah shit.
SPEAKER_00Okay, Lindsay. This is Ghost in the Machine, and this song is called Enemy of the State. They're fucking amazing. It is time. Let's do it.
unknownWhisper.
SPEAKER_03Lindsay, what do you think? They were absolutely amazing. Yes. And you can find them on Instagram at GITM Official. And in their bio, it says that they are an alternative music genre blenders. And they have a new video out called 3 AM on YouTube.
SPEAKER_01I love it.
SPEAKER_03Yes. It felt like the 90s. The 90s. I loved it. And I'm just scrolling through their videos and they look really cool. Really fucking cool.
SPEAKER_00Really fucking cool. Yes.
SPEAKER_03And they have collabs with other artists. So yeah. Go follow them on Spotify or whatever music platform you listen to and on Instagram immediately. Mm-hmm. And once again, if you win the lottery, be careful with that shit. My God.
SPEAKER_00Yes, and Lindsay. Lindsay. This is for the band. This is for you. Oh my god. What a fucking story. Shit. Bing bang bing.
SPEAKER_03Yeah, that one's the one I've had in my in my purse for a while. You have to be bit careful not to do um one or two parters before our hundredth episode because we just had like a couple of those in a row. So I was able to combine this all into one. And like I said, I mean, I've said this like 10 times already, but I'm gonna say it one more time. The information is conflicting. So this was really hard for me. I just need y'all to know that. This was a struggle for me to put together. I hope I put all the right info out there.
SPEAKER_00So you listen to like other documentaries and other people, and then they weren't the same. So you were just like, hey, let me just put it.
SPEAKER_03The amounts of money were different, but what I did figure out, and like I said, the initial was 30 million after taxes was 17, after he got the lump sum was 12.7.
SPEAKER_00Lindsay over here doing some gonzo journalism.
SPEAKER_03God, like I was like, okay, I've got all the information I need. Then I look and listen to something else, and I read, I watched another documentary and I was like, fuck. But yeah. So I do want to say really quick, the documentary on Web of Lies, that is based around uh this group of web sleuthers. And they are really good.
SPEAKER_00They're really cool.
SPEAKER_03Yeah, they less cats. Yeah, like people out there that are not a part of law enforcement are out there doing the work.
SPEAKER_00Better than some law enforcement.
SPEAKER_03Yeah, Dave, he he joined up with them. And it was like, how do you have this info? I ain't got it. Because they are out there, like I'm telling you, and a lot of them are women.
SPEAKER_00They're doing away. I'm overintended and I'm super infatuated and I'm hyperly focused right now.
SPEAKER_03Well, yeah, because we want to know. We want to know everything down to the nitty-gritty. What happened, why, everything. And Didi, she was getting on these forums, and she was like clapping back at people, then took herself out of the situation and came back and was like, oh, that was actually my son. She blamed her son for a lot of shit.
SPEAKER_00Her 14-year-old son.
SPEAKER_03Yeah.
SPEAKER_00Shit.
SPEAKER_03You don't deserve children, ma'am. So sorry to tell you. But you know what? She'll be in prison forever. She's exhausted her appeals, and nobody's believing your bullshit, Didi.
SPEAKER_00Yeah, we will keep paying taxes here in Florida for you. That way you can set the.
SPEAKER_03Yeah, she's in uh Hillsboro, down in Tampa.
SPEAKER_00Well, fuck's sake.
SPEAKER_03I know.
SPEAKER_00I was kind of like, dude, I was just taking in the story the whole time, and then all of a sudden you drop the bomb on me.
SPEAKER_03Well, I hate people that take advantage of other people that don't know any better. I really fucking have a darkness in my heart for people that do that. I just, I think it's fucking terrible. I don't understand why there is a mechanism in somebody's brain that'll be like, oh, they don't understand. Instead of helping them, let me take everything they've got and make a fool out of them.
SPEAKER_00Yeah, they're the weakest kind of predators. Or murder them. Because they prey on the weak. Instead of actually fighting for what's right, yeah.
SPEAKER_03Abraham was probably just like, oh my god, this lady can help me figure out all this business shit that I don't really know much about. And it was it's really sad because he was just trying to help everybody that he knew, you know? Yeah. Sons of but we appreciate you guys listening to our rants and our raves and our stories, and especially like, think I mean, follow these bands.
SPEAKER_00Yeah. It was a great fucking palate cleansing type moment. And we're gonna check out the whole catalog, and you should too.
SPEAKER_03And I've I just want everybody to know I have been jamming to Electric Cowboy like all day. I've just been in a dance mood, and they are my metal dance band right now. And I also love the browning, like get down to them. Put on some electric cowboy, put on some of the browning, put on ghosts in the machine. Yeah. We got it right, right? Okay, yeah, ghosts in the machine, and because they're a very dancy, like you can dance to that shit too.
SPEAKER_00And it's a little nine-inch nails-ish, like kind of got that whole like down to some nine-inch nails. Industrial on the edge of like metal and at the same time, a little prodigy kind of pit shifter. Yes, pit shifter is one of my favorite bands, by the way. And I don't know if y'all know who pitch shifter is, but check that shit out. But I love that kind of shit.
SPEAKER_03We're gonna listen to him tomorrow. We're gonna start the day with pit shifter while we're painting doors.
SPEAKER_00It was so badass. And they still riding the wave. I love it. So check out us on all of our socials. You can go to drinkabout something.site and you can go to Lindsay's Instagram, which is drinkabout something. No, Jesse. It is our Instagram, drinkaboutsometh.org.
unknownStop.
SPEAKER_03Drinkabout something on Instagram.
SPEAKER_00Yeah, drinkabout something on Instagram. On TikTok. On TikTok has a Lindsay one.
SPEAKER_03Drinkabout something pod underscore Lindsay.
SPEAKER_00I should know this by now.
SPEAKER_03You should.
SPEAKER_00No.
SPEAKER_03Where are we at on YouTube?
SPEAKER_00Just type in Gen Z, J-E-N-D-S-E-Y. At least I got that part right. Yeah, Lindsay. Because I've been fucking up this whole podcast, but y'all won't know it. You probably will. I might leave all this shit. Anyhow, I want to get the hell out of here. We love you guys so much, and we will see you next Friday. We're fixing to close out season number two, and I'm so excited!
SPEAKER_03Yay! Because we're gonna have a party.
SPEAKER_00Can't you tell that the energy drink just kicked in?
SPEAKER_03I can tell.
SPEAKER_00Yeah, because I'm all like.
SPEAKER_03Baby, get again again.
SPEAKER_00Yes. All that, yes. And we're gonna go watch uh old school. Old school, yeah, because uh fucking never know. Yeah, you drop them F bombs in the middle of some wedding singing, and that's that's how I fall in love. We'll see you guys next Friday, though. We love you so fucking much! Bye.
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