Small Town Murder – "The Unluckiest Winner – Plant City, Florida"
Podcast: Small Town Murder
Hosts: James Pietragallo & Jimmie Whisman
Episode Date: February 12, 2026
Episode Overview
In this episode, James and Jimmie explore the incredible, tragic, and almost unbelievable story of Abraham Shakespeare, a laborer from Plant City, Florida, who won a $30 million lottery—and then vanished. The episode is a wild ride through small-town absurdity, greed, betrayal, and murder, featuring their trademark blend of in-depth research and sardonic banter. Along the way, the hosts roast the quirks of rural Florida, the perils of sudden wealth, and the spectacular ineptitude of the story’s villain.
Key Discussion Points & Insights
1. Introducing Plant City, FL
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[04:54] James: “We are going to Florida this week. Here it is. We are the panhandle of all panhandles.”
- Location: Rural town blending “country living” and modern growth, close to Tampa.
- Town reviews: Ranging from nostalgic praise about “cornbread and chicken” (08:25) to complaints about rampant rudeness and surprising levels of crime.
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[13:30] Demographics and Economy:
- Population: ~39,000.
- Median income below national average; housing relatively affordable but trending upward.
- Hosts roast the area’s abundance of trailers, crime stats, and the annual "Florida Strawberry Festival"—which, to their amusement, fails to attract Ludacris or Nelly as its headline act (18:01).
2. Abraham Shakespeare’s Life Before the Lottery
- [24:19] The Most Interesting Name:
- “Abraham Shakespeare is his name... That’s the coolest name of all time that we’ve ever covered, right?”
- Grew up poor, did not progress past 7th grade, illiterate, in and out of juvenile detention and prison (29:55).
- Held menial labor jobs, described as a “gentle giant” who struggled to keep steady work but was generous and well-liked.
3. Winning the Lottery – A Poisoned Gift
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[40:14] In 2006, while working as a truck driver’s assistant with just $5 in his wallet, Abraham handed $2 to his coworker Michael Ford for two lottery tickets. One hit every number:
- $30 million prize (41:17).
- He opted for the lump sum (~$17 million after taxes).
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Immediate Fallout:
- Abraham tried to remain humble, buying a BMW and a gated home, but still wore “high-water pants and Reeboks” and continued shopping at Walmart (48:44).
- Family and friends began to swarm for handouts. He was exceptionally generous:
- Paid off mortgages, bought friends cars, gave cash to strangers, homeless people (50:25).
- “Santa Claus of Lakeland” (50:46).
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Famous Quote:
- [43:52] (Greg Smith, his friend): “He didn’t grab his wealth and immediately run. He stayed in the community where he lived. That’s a mistake. You can help people from a distance.”
4. The Beginning of the End: Greed and Exploitation
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[57:04] Abraham distributed over $13 million in two years.
- By late 2008, he was down to $3.5 million.
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[63:54] Michael Ford sued him, claiming the winning ticket was his. Jury rules in Abraham’s favor.
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Abraham become increasingly overwhelmed—hundreds of calls per day for handouts.
- “All these people want his money from me. I’d have been better off broke.” (74:41)
5. Dee Dee Moore – The Queen Con Artist
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[76:59] Enter Dee Dee Moore, a flamboyant local businesswoman with a history of fraud, arson, and pathological lying.
- Poses as a financial advisor, promising to protect Abraham from moochers and collect loans for him.
- Quickly gains his trust and, within months, gains control of all his assets and bank accounts (99:03).
- Spends his money on a Corvette, a Hummer, lavish trips, and gifts for her much-younger boyfriend.
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Memorable Red Flag:
- [101:36] She forges LLC board meeting notes—in which she's the sole attendee—to grant herself total control over Abraham’s money.
6. Abraham Disappears
- [108:07] Spring 2009, Abraham vanishes.
- Dee Dee gives conflicting stories: He’s in Texas, Jamaica, Haiti, on a cruise, has AIDS, is hiding from moochers, etc. (108:43)
- Mass texts from his phone to friends and family use words Abraham would never use or spell correctly (110:39).
- Dee Dee moves into his mansion, throws out his possessions, and tells his mother different stories about his whereabouts.
7. The Investigation Unravels the Plot
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[113:01] Eight months after he vanishes, a cousin files a missing person’s report.
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Investigators and web sleuths soon zero in on Dee Dee, uncover her fraudulent behavior and financial manipulations (122:41).
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Dee Dee tries to cover her tracks by:
- Faking texts from Abraham.
- Paying friends to impersonate him on calls to his mother.
- Offering bribes and gifts for people to “verify” he’s alive (168:29).
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Bizarre, Incriminating Behavior:
- [134:46] Dee Dee is caught on tape, orchestrating forged letters, asking an undercover cop to take the blame for “drug dealer Ronald’s” murder of Abraham, and providing the location of Abraham’s body.
- She hands over the murder weapon—the gun registered to her.
8. “We Look Up, and We See Dee Dee Moore” – The Trap Closes
- [137:00] Dee Dee shows an informant exactly where Abraham is buried—beneath a newly poured slab of concrete.
- She even tells him to “bring marshmallows” for burning the body (140:17).
9. The Interrogation and Prosecution
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[145:49] Dee Dee gives many outlandish explanations in her interrogation—blames drug dealers, her ex-husband, her cousin Cedric, a random lawyer, and finally her own 14-year-old son RJ (“My 14-year-old son shot him,” 163:06).
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[181:57] At trial, she is found guilty within three hours.
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Judge’s rebuke:
- [181:52] “Cold, calculated, cruel. They all apply…probably the most manipulative person this court has ever seen. Abraham Shakespeare was your prey and your victim. You, ma’am, may fuck off.”
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Sentence:
- Life without parole, plus 25 years for use of a firearm.
10. Aftermath & Reflections
- The assets are assessed and clawed back.
- Dee Dee continues to deny responsibility in prison interviews, even lobbying for laws to protect lottery winners’ identities (183:20).
- Abraham’s mother dies in 2023; his son Moses’s mother later wins $1 million on a scratcher (182:35).
Notable Quotes & Memorable Moments
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On Sudden Wealth:
“People think that money cures problems, but it really magnifies them.” — Don McNay, lottery expert [52:00] -
On Florida:
“A panhandle of panhandles…just two panhandles welded together.” — James [04:54] -
On Dee Dee’s Deflections:
“His name’s Ronald. Oh yeah, tall guy, red hair…Maybe smelling of hamburgers is possible.” — James, riffing on her shifting lies [151:33] -
On Con-Artist Mentality:
“She tells the fibbiest fibs. My daughter’s a goddamn liar.” — Dee Dee’s father [91:05] -
On Small Town Crime:
“On the spectrum of an alligator hopped up on meth…Over here it’s like a gerbil on Sudafed.” — James, on Polk County comparison [24:04] -
On the Host’s Warnings: “Move away from the people who know you have money. You can help them from afar. Don’t have the people you don’t know coming up to you.” — James [68:53]
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On Being Set Up as the Killer’s Witness:
“I’m not going to get caught.” — Dee Dee, unaware she’s being taped, before giving up all the evidence [133:12]
Key Timestamps for Important Segments
- Intro and Town Breakdown: 00:25 – 18:00
- Abraham’s Early Life: 24:15 – 36:00
- Lottery Win and Early Generosity: 39:49 – 57:04
- Dee Dee’s Arrival and Swindle: 76:59 – 108:07
- Missing Person, Investigation, and Web Sleuths: 113:01 – 124:03
- Wire Recordings and Dee Dee’s Mistakes: 133:12 – 144:02
- Interrogation and Dee Dee’s Defense: 145:49 – 166:50
- Trial and Sentencing: 176:01 – 181:57
- Aftermath & Epilogue: 182:35 – End
Tone and Language
The hosts maintain a wry, irreverent, and empathetic tone throughout, frequently lampooning both the audacity of Dee Dee’s schemes and the bleak absurdities of small-town life and lottery luck. Their sympathy for Abraham’s naive generosity is sincere, as is their scorn for those who exploited and ultimately murdered him.
Final Thoughts
This episode is a must-listen for fans of true crime that walks the line between heartbreakingly tragic and jaw-droppingly absurd. James and Jimmie’s comedic, yet deeply human perspective on Abraham Shakespeare’s luckless windfall and the psychopathic greed it attracted is both insightful and highly entertaining.