In this Account, a summary of our work on the synthesis and chemistry of chiral molecular tweezers and certain related species is presented. The framework around which the structures to be discussed were built was Kagan's ether, a short history of which will be given. Chiral molecular tweezers of various sizes were constructed and shown to exhibit binding to various pi acids. An analysis of chiral recognition was performed using variable temperature chiral high-performance liquid chromatography. It was shown that the chiral discrimination was essentially enthalpic in nature. Other forays into the chemistry of Kagan's ether analogues have also been made through the synthesis of a chiral catalyst and a chiral molecular square.