Kellyanne Conway
The sideways smiling Republican strategist and campaign manager turned counselor to the President-Elect may be more famous to the public for her SNL persona than her political work. The former beauty pageant contestant, mother of four, co-author of What Women Really Want: How American Women Are Quietly Erasing Political, Racial, Class, and Religious Lines to Change the Way We Live, is said to be the Trump-whisperer, advising him largely, it seems, on how to politically approach women. Kind of a losing job is you ask us.