John Bolton
As a lawyer for the Bush campaign during the 2000 Florida recount, John Bolton was held in such high esteem that Dick Cheney said Bolton was deserving of any job he wanted. Five years later, the walrus-mustached gentleman who had previously said about the United Nations that "The Secretariat building in New York has 38 stories. If it lost ten stories, it wouldn't make a bit of difference" was nominated ... get ready ... for U.S. Ambassador to the United Nations. Oh, the irony.
Senate Dems (and some Republicans) were not having it, though, resulting in Bush having to appoint Bolton a temporary representative to the U.N., where his confrontational manner meshed none too well with the purposefully deliberative body. When the president again submitted Bolton's nomination in 2006, Bolton decided to ditch the job.