jockstrap award means in slang: Sometimes, the term “jockstrap medal” is also used in slang. It is meant to indicate that someone is more talented than them and has made it big. Jockstrap awards or jockstrap Medals are ‘given’ to people who have achieved success through being in the right place at a right time and not necessarily their talents. (in Slang Dictionary, added by Epifanía Giménez)