Herman Cain

Herman Cain and MLB umpire Jerry Layne
Full Name: Herman "9-9-9" Cain
Status: Out of the race
Offices Held: None (That's his appeal!)
Notable Occupations: President and CEO of Godfather's Pizza (1986-1996), Chairman of the Federal Reserve Bank of Kansas City (1995-1996), CEO of the National Restaurant Association (1990s).
Why He Would've Won: After spending months mired in the single digits, Herman Cain shot up in the polls to be the Republican frontrunnner. Cain's straight talk ("...If you don't have a job and you're not rich, blame yourself!") and flagrant disdain for knowledge ("Ubeki-beki-beki-beki-stan-stan") endeared him to Republican primary voters desparate for a frontrunner who isn't Mitt Romney. Though not as rich as previous business candidates like Ross Perot and Steve Forbes, Cain has the Republican fundraising titans the Koch brothers to keep his campaign coffers full and his ridiculous campaign ads on the air (see below). Much of Cain's success is owed to his "9-9-9" tax plan, which is so simple, a child playing SimCity could figure it out, assuming that child's parents could afford a computer under Cain's lopsided tax plan.
Why He Would've Lost: The problem with businessman presidential candidates historically has been a flameout rate of about 100%. At the end of the day, most voters want candidates with some foreign policy chops, and Cain's stated reliance on "experts" for such matters might leave a bad taste in voters' mouths like so much week-old Godfather's pizza. Couple that with Cain's uncanny ability to contradict himself in the span of a few words, and Republicans may decide Mitt Romney isn't so bad, after all.