George Washington. Just sayin’.
True, the Continental Congress selected him CiC of the Continental Army, where he directed the actions of, at most, 16,000 men. Whereas Herman Cain was selected by Pillsbury to be CEO of Godfather’s Pizza and its >20,000 employees. Just sayin’.
Hey!! You know who else never won an elective office before becoming President? Thomas Jefferson. True, he was Adams’ V.P. But that was back when the VPOTUS was officially “Number Two”. So Cain has won just as many elections as Jefferson had, while losing one fewer.
It’s odd, really, how this country survived and thrived despite having total incompetents like Washington and Jefferson at the very beginning.