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Drink about something · August 28 · 59 min

EPISODE 97: Abraham Shakespeare

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 LET US KNOW WHAT YOU THINK!!! Ready to explore more shocking true crime cases with us? Subscribe to Drink About Something for new episodes every Friday, and visit drinkaboutsomething.site with links to see all our content, including visual evidence from the cases we cover. AS ALWAYS D-A-S

0:00 · Lottery Fantasies And Friday Drinks-59:15
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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


LET US KNOW WHAT YOU THINK!!!

Ready to explore more shocking true crime cases with us? Subscribe to Drink About Something for new episodes every Friday, and visit drinkaboutsomething.site with links to see all our content, including visual evidence from the cases we cover. 

AS ALWAYS D-A-S

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