In a typeless world, our discussants have spent two decade trying to bring order, and perhaps even soundness, by democratizing types and pushing them where, according to many, they didn’t belong. Matthias Felleisen worked on soft typing for Scheme, semantic contracts, and Typed Racket. Gilad Bracha worked on Strong Talk, optional types for Java, and now Dart. The discussion will shed light on the history of optional type and gradual types, their position in today’s software landscape, and their prospects for world domination.