20/20 - The After Show: Unlucky Numbers

Episode Date: April 21, 2025

A man wins $30 million dollars  in 2006 from the Florida lottery, but three years later, he mysteriously vanishes. His case would become a tangled whodunnit. Deborah Roberts talks with ABC’s Matt Gutman about his prison interview with the convicted killer.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

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that adds tons of natural light to its roomy cabin, and ambient lighting sets the right vibe. So crucial in dreary winter days. The Bose Premium Sound System helps you escape further into your favorite music. The Nissan Murano and all its features gives you the greatest rush, Hi there everybody, welcome to 2020 The After Show. I'm Deborah Roberts and boy we've got a great episode for you today because have you ever just thought wow wouldn't life be great if I won the lottery? You might think twice after hearing about our most recent 2020 story

about Abraham Shakespeare, the Florida lottery winner who was tragically murdered for his winnings. Joining me to talk about this is the fabulous Matt Guttman, our chief national correspondent here at ABC News, who reported Friday night's 2020 episode. Hi, Matt. Hey, Deb. How are you? I'm good. Welcome. Welcome. Before we jump into this, I mean, first of all, so many people know you for just crisscrossing not just the country, but the world. I mean, from the wildfires in California, you're in the Middle East a lot, reporting over there.

Give us a sense of what it's like as you are. I mean, I thought I was busy, but man. You know what's really funny is I had to go back to look at some of the old videos that we did back in like 2012, 2013, when I first started doing this story and when we interviewed Dee Dee and Greg Smith. You know, I was much younger,

I was still in my mid thirties and I realized, holy cow, I look so tired because I was crisscrossing the country so much back then. I'm like, dude, what is wrong with you? Get some rest, get some sun, boy. It was actually very interesting. But yeah, I'm in LA in my little cave office here, so I'm happy to be sedentary right now.

Well, it's good to be able to talk to you and find you some time to sit so we can talk about this. And I remember this case of Abraham Shakespeare long before we obviously got into it. A man who went from rags to riches, he had been a janitor and won 30 million dollars in the lottery back in 2006. Newfound fortune just kind of transformed his life. He'd been a sanitation worker and he started giving back as many people say they would love to do if they got this kind of money. But after a while, friends started

to notice that he just seemed to feel burdened. You know, everybody had their hands out wanting some of his money. And then three years after the lottery success, he mysteriously disappears. And everybody is talking about this case and what happened. And of course, police go undercover to try to figure out what happened. So before you and I get deeper into it, let's take a listen to some of the moments from your reporting, including some of the folks who are closest to him and everything in the aftermath of the winning ticket. Right here at this gas station in a town with a name you just

can't make up. Frost proof Florida, one stop, two quick pick lottery tickets, one of which would change his life forever. A jackpot worth 30 million dollars I looked up at him and I looked at the ticket again and I looked up at him I Said you I said you've won 30 million dollars. He said okay. I just wasn't sure I Needed somebody I could trust to tell me that. And I was like, do not show this to anybody else. You go to Tallahassee and cash this in immediately. When Abraham won the lottery, all of Lakeland and Polk County won the lottery.

People did not hesitate to come to Abraham and say, you know, I need money for my mortgage. They've got to foreclose my house, but they're gonna rep money for my mortgage. They've got to foreclose my house. They're going to repossess my car. I've got to bury my mother. I mean, everything you can think of that someone needed. Now you're dealing with all kind of people you want to look out for and people

you don't want to look out for, but everybody's there saying, give me, let me, let me have. So it was just overwhelming for him. There were days that random women with car full of kids would pull up and say, oh, the Lord led me to you. And I would be like, no, that would be Google Maps, honey. Folks who are in his orbit. I mean, Matt, this is just unbelievable

when you think about all of this. As you said, you almost can't make this stuff up. And I know Lakeland, Florida a little bit. I reported in Florida over the years and spent some time. Give us a sense of what somebody in that area would be dealing with. I mean, it's a small town. Everybody knows you. I mean, what was that like?

What were your impressions of the town and what Abraham was facing? Well, I mean, just going back to the house where he lived in, Deborah gives you a sense of the distance he had traveled from the moment he purchased that ticket to when he cashed it or finally got to cash it after some lawsuits. It's basically a shotgun shack, this crumbling house in Lakeland. And as was noted in that clip that you just put out, there were literally people camped outside of his house for months waiting for handouts.

He couldn't leave the house without people physically accosting him, asking him for money, because he really was incredibly generous in the beginning. All he wanted to do was help out his people. And there were lists that he carried around of people, names, and the amounts of money. And one of the major problems

and one of the, you can't make this up things about this story is that Abraham Shakespeare was functionally illiterate, right? So he needed a lot of people to help him. He couldn't write text messages really. So there were people helping with his phone, people helping him with his accounts, people helping him keep tabs of all the money he was handing out. But it just became too much. And you know, in 2006, you suddenly have $17 million and he took the lump sum. So the total

was 30. He took the lump sum. That is life changing, community changing money. For anybody. And he was for anybody. But especially then, especially in Lakeland, Florida. And it was in the news, it was in the local news, everybody knew this guy, suddenly he was a celebrity. He was the kind of guy who didn't, we said he was a janitor,

but he didn't actually really have a job. He would do odd jobs all the time. He would go to, you know, this barbershop owned by a guy named Greg Smith, who becomes very important in the story later on. And you know, he would just sweep the hair off the floor, do whatever he could to get a meal and get some money. So it was an enormous distance that he covered by winning this lottery. And of course, it did not end well for him. Yeah and so many of us of course as reporters have

reported on stories either kind of adjacent to this when you talk about in the piece the curse of the lottery it's kind of that trope with that idea that yeah everybody would love to win millions of dollars but it can just sort of ruin your life and in this case it was devastating within three years all of a sudden this guy is missing. Yeah, I went back again to watch some of the old videos from 2013 and one of the clips is this old clip of Greg Smith who was the barber who essentially created this catch can in a Red Bull can put a microphone inside and recorded Dee Dee

Moore essentially getting her to more or less confess to murdering and sort of disappearing Abraham Shakespeare. But Greg Smith was pretty close to him, and Greg recounts a story of one day deep into the mess that Abraham Shakespeare had sort of been immersed in because of the winnings. And Abraham Shakespeare, who's been like handing out money right and left, comes in and he's like, you know, Greg, I wish I could go back to my old life. I wish I could go back to the time before I had this money. I could just live free and be myself because I can't be myself. And that desire to sort of get out not only caused Abraham Shakespeare to go and move into a gated community

where he thought he might be protected from all these people looking for the handout, the loan, the payout. There were women who were coming who were saying that their children were his illegitimate children. Like people were literally coming out of the woodwork. So he was trying to inoculate himself from them, trying to create some distance, which is why he moved to this house on the edge of town

in a gated community. And it's why when Didi Moore actually murdered him, she was able to cover her tracks by making this video in which you basically hear Abraham kind of saying he's ready to check out, move away, maybe California, maybe Cozumel, go on a cruise, and why people believed for a long time that he really did disappear.

That he just decided to step away from it all. Yeah, get out of the rat race. And that was one of the twists and turns in this story too because for months he's gone and they're texting, DD is of course sort of setting these up. We're gonna take a quick break and Matt, we're gonna talk about your thrilling sit down interview with that convicted killer of Abraham Shakespeare.

Stay with us. Don't miss Good American Family. Shakespeare. Stay with us. Inspired by the shocking stories that tore a family apart. I don't know what's going on. How old are you? You should get a lawyer. You have no idea how those people hurt this girl. The Hulu Original Series. Good American Family. New episodes Wednesdays, streaming on Hulu. Barty Avenue and Green Bay. To all of these men, I want to say that football is not just a game, but a way of life. Whose lifelong dream of making it to the league. Each man must make a personal commitment to excellence and to victory. Will be fulfilled on this iconic stage at Lambeau.

The 2025 NFL draft begins Thursday, April 24th at 8 p.m. Eastern on ESPN, ABC and NFL Network. Welcome back to 2020 The After Show where I'm talking with my colleague and friend Matt Gutman. Matt, one of the most striking things about our program to me was that interview you did with Dee Dee Moore while she was behind bars in prison. I mean she was professing her innocence. What was that like for you to sit there? Deborah, you've done this many times as well, right? The jail interviews are some of the most nerve-wracking things

we do because you have a very limited amount of time with this person. The prison prescribes exactly how long you have. They have everything set up. There are all these parameters. There's a lot riding on a very short period of time where you have to get all your questions in and hope that this inmate whose life is either on the line or who faced life in prison without

parole play ball with you and in the case of Dee Dee Moore she she came to play I mean it was one of the most astonishing, confounding, frustrating experiences. So she sits down and right away she admits no guilt. And it pretty quickly goes off the rails when I'm trying to call her out on the fact that there is a mountain of evidence which the jury saw, which is why they just convicted her of murdering Abraham Shakespeare, including the fact that his body was found under a slab on her property. In her backyard, yeah. Yeah, in her backyard. I mean, that's not great that she concocted the video she concocted, the letters, the text messages

from Abraham. And yet, Deborah, she continues to say that there's another guy, there's a drug dealer named Ronald out there, that there's a woman named Deanne who has, who's a witness who has the key to everything. And look, Deanne sent a letter. And nobody's ever met these people and there's no evidence that they exist. No, and the letter, Deborah, was in her handwriting. It's like, Deedee. Your producer Tom Berman said your eyes were about to pop out of your head. Well, hold on a second, Matt, because I want to play an extended clip from your interview with Dee Dee Moore. Let's take a listen. I lied about a lot of things. I told you that. I didn't have a choice.

What did you lie about specifically? The note with Abraham Shakespeare's mom, stuff like that. I had no choice. They were threatening my son. I didn't have a choice in that. So I- If you say a lot of things, but then you only mentioned one thing. Maybe you didn't lie about that much.

There were so many little inconsistencies because I'm trying to figure out what they've done to him. So like when I'm talking to the detective, like with Greg Smith and I'm trying to figure out what they've done to him. So, like when I'm talking to the detective, like with Greg Smith, and I'm talking to him about things, you know, I'm trying to figure out what they've done with Abraham, and so... In the recordings from your conversations with the sheriff's office,

you give so many different versions that it's absolutely bewildering. Why is that? I'm threatened. They're making me do that. So you're lying to the police because you feel threatened I'm threatened. They're making me do that. So you're lying to the police because you feel threatened? No, I'm being told to do that. I'm being told to just keep throwing them off.

I mean, when she started talking, so there's a duality that happens that I know you've experienced, Debra, which is you go into these prisons and you interview these people, and very often it's after conviction, sometimes it's before, and so these people have been judged by a jury of their peers. They've

been convicted by 12 people who've been presented often a very significant amount of evidence against them. And she becomes very small. That's a very gentle tone. She's trying to be convincing and trying to be... And she sounds very articulate in her explanation. And very endearing. But this is a woman who was found guilty, and the evidence is enormous against her, of firing bullets into Abraham Shakespeare, then carrying the body outside, somehow getting it, like a hundred yards from her house to that field, then burying the body. This is a tough, physically strong woman

who was capable enough to have this nursing staff agency and capable of making these businesses, but also capable of concocting this story of torturing Abraham Shakespeare's mom by making her think that he was alive, by covering up her tracks, and then by murdering this guy in cold blood solely because she wanted his money.

It was hard to square the two. And then when she started talking about, you know, trying to convince me of her innocence by saying that she loves Donald Duck and Daffy and Minnie Mouse and all that stuff because, you know, she knows that ABC News is owned by Disney. It was so preposterous and so ludicrous

and frankly a little offensive. Of course, of course. Well, what's so sad about it when you think about it too? This man had all this money and at the end, she's manipulating him out of a million dollars, which is all he had left. Matt, hold on a second. We're gonna take one more break.

After that, the undercover tactics that lead law enforcement right to the body of Abraham Shakespeare. So stick around. Hey, I'm Brad Milkey. You may know me as the host of ABC Audio's daily news podcast, Start Here, but I'd like to add aspiring true crime expert to my resume. And here's how I'm going to make it happen. Every week, I'm going to unpack add aspiring true crime expert to my resume, and here's how I'm going to make it happen. Every week, I'm going to unpack the biggest true crime story that everyone is talking about. ABC's got some unique access here, so I'll talk to the reporters and producers who have followed

these cases for months, sometimes years. We're bringing the latest developments and the larger context on the true crime stories you've been hearing about. Follow the crime scene for special access to the people who know these stories best. We are back with Matt Gutman talking about the episode of Abraham Shakespeare. Matt, this story was so bizarre. As you said, you almost can't make this up. And it was sort of cracked for law enforcement when Greg Smith, whom you mentioned earlier, who was an acquaintance of Abraham Shakespeare, and he actually went undercover with police to try to help solve this case. So he owned a barbershop, Greg Smith did. And Dee Dee Moore, she said, basically, I'll give you some money if you help me convince

Abraham Shakespeare's mother that he's actually alive or she didn't say he's dead, but you know, just call the mother to assure her that Abe is okay. So Dee Dee Moore takes Abraham Shakespeare's mother out for a meal and it's super loud in this restaurant and oh, suddenly the mom gets a call. Oh look, oh, Abe's on the phone. And he sounds a little different, he sounds a little weird. And then it's Greg Smith the whole time explaining to the mother, hey, I have a cold,

I just wanted you to know, I'm okay, don't worry about me. It was just before Christmas. It's a short conversation, he hangs up. So that was supposed to be the proof of life showing that Abe Shakespeare is alive. At some point, Greg Smith and Didy Moore meet at a mall parking lot and she hands him money. It just so happens that the cops are already watching Didy Moore, watching her give money to this guy, Greg Smith, and then he leaves the parking lot of the mall.

They follow him, they light him up, they take him down. And they're like, you're in big trouble, mister. So then he decides to help police and he helps solve this case. As you said, he actually goes undercover and tapes her. And we learned that, of course, then she's convicted. Tell us where the case is now, Matt, because she's tried to appeal a couple of times.

Yep. She has claimed that she had counsel that was not sufficient, that she wasn't properly represented, and the judge has thrown that she had counseled it was not sufficient, that she wasn't properly represented, and the judge has thrown that out. The judge was not happy with this case that she presented before the courts, and he tossed it out pretty quickly. She is now still in prison, facing a sentence of life without the possibility of parole,

which means that unless one of her additional appeals works, she will die in prison. She'll spend the rest of her life in prison. What a story, Matt. You did such a great job covering this. So thanks so much for being with me today, Matt. Great seeing you or talking to you anyway. It was fun. Same here.

Matt Gutman is the chief national correspondent for ABC News. Don't forget, of course, to tune in on Friday nights at 9 for all new episodes of 2020 on ABC. The 2020 After Show is produced by Cameron Chertavian, Sasha Aslanian, with Joseph Rea, Tom Berman, Brian Mazursky, and Alex Berenfeld of 2020. We had technical help this week from Trevor Hastings and Kevin Ryder. Theme music by Evan Viola and Janis Johnston is the executive producer of 2020. Josh Cohen, the director of podcasting at ABC Audio. Laura Mayer is the executive producer.

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