Why did the “best and brightest” of the Kennedy and Johnson administrations continue with a flawed Vietnam strategy despite years of wargaming simulations warning that there were no good outcomes for American involvement? Jacquelyn Schneider, the Hoover Institution’s Hargrove Hoover Fellow and director of Hoover’s Wargaming and Crisis Simulation Initiative, discusses the role of the 1960’s “SIGMA Games” in deciding Southeast Asia options, how wargaming influenced America Cold War strategy, its use in making sense of present-day enigmas (China, Russia), plus the challenges in playing out scenarios in the “final frontier” that is outer space.