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
Chapter 1: Who are the hosts and guests introducing the story of Abraham Shakespeare?
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 Gutman, 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-30s 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 L.A. in my little cave office here. So I'm happy to be sedentary right now.
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Chapter 2: What was Abraham Shakespeare's lottery win and the impact on his life?
Thank you so much for having me. 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 happened. 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. Frostproof, Florida. One stop. Two quick pick lottery tickets, one of which would change his life forever. A jackpot worth $30 million.
I looked up at him, and I looked at the ticket again, and I looked up at him. I said, you've won $30 million. He said, OK. 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. 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 cars 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?
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Chapter 3: How did Abraham Shakespeare's lottery win affect his relationships and community?
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, Debra 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. You know, 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 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.
You know, he was the kind of guy who didn't, you know, 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, 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.
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
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Chapter 4: Why did Abraham Shakespeare move to a gated community and what challenges did he face?
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 Dee Dee 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 their text and D.D. is, of course, sort of setting these up. We're going to take a quick break. And, Matt, we're going to talk about your thrilling sit down interview with that convicted killer of Abraham Shakespeare. Stay with us. This episode is sponsored by the podcast Death County PA from Wondery.
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Hello, it's Robin Roberts here.
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Chapter 5: What led to Abraham Shakespeare's disappearance and the initial police investigation?
Hey guys, it's George Stephanopoulos here. Hey everybody, it's Michael Strahan here. Wake up with Good Morning America.
Robin, George, Michael, GMA. America's favorite number one morning show. The morning's first breaking news. Exclusive interviews. What everyone will be talking about that day. Put some good in your morning and start your day with GMA.
Good Morning America.
Put the good in your morning. GMA 7A on ABC.
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?
Debra, 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 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 that 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.
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Chapter 6: What insights did Matt Gutman gain from his prison interview with Dee Dee Moore?
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'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, Debra, was in her handwriting.
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.
Chapter 7: How did Dee Dee Moore respond during the prison interview about the murder accusations?
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.
You say a lot of things, but then you only mention 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 TALKING TO HIM ABOUT THINGS, YOU KNOW, I'M TRYING TO FIGURE OUT WHAT THEY'VE DONE WITH ABRAHAM.
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?
No, I'm being told to do that. I'm being told to just keep throwing them off.
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