Have you ever fantasized about being ridiculously wealthy? Probably. Striking it rich is among the most resilient of American fantasies, surviving war and peace, expansions and recessions, economic meltdowns and global pandemics. We dream of the jackpot, the big exit, the life-altering payday, in whatever form that takes. (Americans spent $81 on lottery tickets in 2019, more than the GDPs of most nations.) We would escape “essential” day jobs and cramped living spaces, bury our debts, buy that sweet spread, and bail out struggling friends and relations. But rarely do we follow the fantasy to its conclusion—to ponder the social, psychological, and societal downsides of great affluence and the fact that so few possess it. What is it like to be blessed with riches in an era of plagues, political rancor, and near-Dickensian economic differences? How mind-boggling are the opportunities and access, how problematic the downsides? Does the experience differ depending on whether the money is earned or unearned, where it comes from, and whether you are male or female, white or black? Finally, how does our collective lust for affluence, and our stubborn belief in social mobility, explain how we got to the point where forty percent of Americans have literally no wealth at all? These are all questions that sets out to explore. The result of deep reporting and dozens of interviews with fortunate citizens—company founders and executives, superstar coders, investors, inheritors, lottery winners, lobbyists, lawmakers, academics, sports agents, wealth and philanthropy professionals, concierges, luxury realtors, Bentley dealers, and even a woman who trains billionaires’ nannies in physical combat, is a compassionate, character-rich, perversely humorous, and ultimately troubling journey into the American wealth fantasy and where it has taken us.