Some thoughts from a pseudonymous political consultant:
1) The filter for politicians hardly selects for spontaneous television charisma at all until the very highest levels. Typically the types of offices one holds prior to being a Governor or a Senator (Congress, lesser statewide office, Mayor of a medium-sized but not too big city) are offices that select for skill-sets like working a room of a handful of insiders, and avoiding making mistakes; not spontaneously debating on camera. Let’s say at any given point in time there are 1,000 people in the country in one of these “feeder” offices (Congress, Statewide elected officials, mid-city mayors, etc).
2) Governor and Senator positions select a little bit more for charisma and media presence, but not much, and usually they only do so in big expensive contested Senate Races – not in the safe blue or safe red states that most Senators and Governors represent. If I were to hazard a guess, I’d say that no more than 50 out of 150 Governors and Senators were elected in the sorts of elections that test a person’s debating mettle and television presence. This doesn’t seem like a process where one is going to end up with tremendously charismatic TV personalities running for president. But it does pose an interesting puzzle, because it would seem to me that professional entertainers could wipe the floor with politicians.
3) Very rarely do celebrities or CEOs run for offices that are “to scale,” or things that they could easily win. If Carly Fiorina had run for an open Republican seat in Congress instead of Senate on her first shot, she’d be a shoo-in. Ben Affleck would be iffy for Senate, but he’d coast to a victory in Congress (and then Congressman Ben Affleck could easily rise up the ranks and build a political career from there, if he had the patience). When they do run for things that are “to scale” – like Kevin Johnson running for Mayor of Sacramento – they tend to win. When they do things not to scale – Chris Dudley running for Governor of Oregon – they tend to lose.
4) Being an entertainer/CEO is generally a better life than being a politician. This selects for second tier CEOs and entertainers running for office, not first tier ones. Al Franken was an entertaining guy, but he was hardly a first-tier celebrity prior to running for office. For him, running for Senate was a step up in status. For somebody like John Stewart or Stephen Colbert, not so much. Similarly, Bill Gates and Tim Cook have nothing to gain by running for office, so the businessperson candidates we get are generally not first-tier. No offense to Carly Fiorina, she has “succeeded” more than the vast majority of people ever will in her field, but she has dedicated her life singularly to making money, and there’s thousands of people who have done a better job than her. She’s the businessperson equivalent of a State Attorney General, not a Governor or a Senator. Trump fares a little better, but still, there are dozens of more successful businessmen in the U.S. than him. If you were to rank all the politicians in the U.S. in terms of electoral success, all the legitimate presidential contenders would be in the top 150. Would anybody make the case that Carly Fiorina is one of the top 150 businesspeople in the U.S.?
5) This leads to the interesting observation that CEOs and entertainers may be so much more talented at some aspects of charisma than politicians are that a C-list CEO or entertainer might still be more compelling than an A-list politician. And if an A-list entertainer or CEO ever decides to run for major office (like Arnold running for Governor), they’ll have a real shot at winning.