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 impos...