Podcast Summary: 20/20 After Show: Unlucky Numbers Release Date: April 21, 2025
Introduction
In this compelling episode of the "20/20 After Show" titled "Unlucky Numbers," host Debra Roberts delves deep into the tragic true crime story of Abraham Shakespeare, a Florida lottery winner who was brutally murdered for his winnings. Joined by Matt Gutman, Chief National Correspondent for ABC News, the episode unpacks the harrowing journey from Shakespeare's life-changing lottery win to his mysterious disappearance and eventual murder.
Background: Abraham Shakespeare's Lottery Win
Debra Roberts introduces the case of Abraham Shakespeare, a janitor who won a staggering $30 million lottery jackpot in 2006. Initially, the newfound wealth transformed his life, enabling him to give back generously to his community in Lakeland, Polk County.
Notable Quote:
"When you're not worried about doing things the right way, you're free to discover your way. And that's what running's all about. Run your way."
– Matt Gutman [00:03]
Shakespeare's generosity, however, soon became overwhelming as friends and strangers alike sought financial assistance, placing immense pressure on him.
Notable Quote:
"It was just overwhelming for him."
– Matt Gutman [04:02]
Life in Lakeland: Community and Pressure
Lakeland, Florida, a small town where everyone knew Shakespeare, became the epicenter of his struggles. Matt Gutman describes Shakespeare's home as a "crumbling shotgun shack" where people camped outside for months, relentlessly seeking handouts.
Notable Quote:
"He couldn't leave the house without people physically accosting him, asking him for money, because he really was incredibly generous in the beginning."
– Matt Gutman [04:52]
Shakespeare's functional illiteracy compounded his difficulties, necessitating assistance with managing his finances and communications. Despite his generosity, the pressure mounted, leading him to take a lump sum of $30 million in 2006—a decision that would irrevocably change his life.
The Descent: From Generosity to Burden
As the weight of his lottery winnings intensified, Shakespeare expressed a desire to return to his former life, free from the incessant demands of those around him.
Notable Quote:
"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."
– Greg Smith, Barber and Acquaintance of Shakespeare [07:14]
This longing led Shakespeare to relocate to a gated community in an attempt to shield himself from the relentless requests for money. However, his efforts to distance himself were futile as new threats and demands emerged.
The Mystery: Disappearance and Undercover Investigation
Three years after his lottery win, Abraham Shakespeare mysteriously disappeared, sparking widespread speculation and fear. Matt Gutman recounts how the case perplexed law enforcement until Greg Smith, a close acquaintance, took a pivotal role in unraveling the mystery.
Notable Quote:
"There's 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."
– Matt Gutman [07:14]
Greg Smith's undercover efforts involved recording conversations with Dee Dee Moore, the woman convicted of Shakespeare's murder. Smith's strategic actions provided critical evidence that led to Moore's conviction.
Interview with Dee Dee Moore: Seeking Innocence
A significant highlight of the episode is Matt Gutman's intense interview with Dee Dee Moore, who maintains her innocence despite overwhelming evidence against her. The interview reveals Moore's conflicting narratives and attempts to shift blame onto fictional characters.
Extended Clip:
Dee Dee Moore: "I lied about a lot of things. I told you that I didn't have a choice." [12:18]
Matt Gutman: "What did you lie about specifically?" [12:23]
Dee Dee Moore: "The note with Abraham Shakespeare's mom, stuff like that. I had no choice. They were threatening my son. You know, I didn't have a choice in that." [12:29]
Moore's inconsistent stories and fabricated accounts further complicated the case, demonstrating her manipulative tactics to evade responsibility.
Notable Quote:
"It was so preposterous and so ludicrous and, And. And frankly, a little offensive, of course."
– Matt Gutman [14:51]
Despite the clear evidence, including the discovery of Shakespeare's body at Moore's property and incriminating recordings, Moore persists in her claims of innocence, making the case even more perplexing.
Law Enforcement and the Breakthrough
Greg Smith's collaboration with law enforcement was instrumental in cracking the case. By going undercover, Smith was able to capture pivotal moments that led directly to Moore's arrest and conviction.
Notable Quote:
"Then he leaves the parking lot of the mall. And, like, you're in big trouble, mister."
– Matt Gutman [16:09]
The undercover operation, coupled with Smith's recordings, provided undeniable evidence that solidified Moore's guilt in the eyes of the law.
Current Status and Legal Proceedings
Despite Dee Dee Moore's attempts to appeal her conviction by claiming inadequate legal representation, the appeals have been swiftly dismissed by the court. She now faces a sentence of life without the possibility of parole, ensuring she will spend the rest of her life in prison unless successful appeals arise in the future.
Notable Quote:
"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."
– Matt Gutman [17:31]
Conclusion: A Tragic Tale of Fortune and Misfortune
The episode "Unlucky Numbers" offers a poignant exploration of how sudden wealth can lead to unforeseen and devastating consequences. Abraham Shakespeare's story serves as a cautionary tale about the complexities of wealth, community pressures, and the darker aspects of human nature.
Notable Quote:
"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."
– Debra Roberts [14:57]
Matt Gutman's thorough reporting sheds light on the intricate details of the case, providing listeners with a comprehensive understanding of the events that unfolded and their lasting impact on the community and those involved.
Production Credits
- Host: Debra Roberts
- Guest: Matt Gutman, Chief National Correspondent, ABC News
- Producers: Cameron Chertavian, Sasha Aslanian, Joseph Ree, Tom Berman, Brian Mazersky, Alex Barenfeld
- Technical Help: Trevor Hastings, Kevin Rider
- Theme Music: Evan Viola
- Executive Producers: Janice Johnston, Lara Mayer
- Director of Podcasting: Josh Cohen
Additional Information
Listeners are encouraged to tune in to future episodes of "20/20 After Show" every Friday night at 9 PM for more in-depth true crime stories, exclusive interviews, and investigative reports.
End of Summary