Why he can win
Say his name! You know who he is. Everyone knows who he is. He's richer than Romney. He's tall. He's been a public figure for most of his adult life. He's usually surrounded by attractive women. His name is synonymous with an over the top wealth, pugnaciousness and clueless bigotry. He never stops talking about how great he is. If he says that often enough some voters might believe it. If nothing else he's not a politician. He could combine his salesmanship with a new found economic nationalism to convince people that they really ought to drop the middleman, and just vote for a dues paying member of the top 0.0001%. People of Trump's class are making many decisions behind the scenes anyway. Why not go full plutocracy? Part of Trump's brand is that he's a fighter who doesn't take any guff from anyone, especially those Chinese or Mexicans who are, in Trump's telling, responsible for everything that's wrong in your life.
Why he can't win
Trump has a very pronounced tendency to take every disagreement or criticism personally. Trump doesn't turn the other cheek or let any attack pass unchallenged. Revenge and payback are virtual Trump sacraments. For a man worth unbelievable amounts of money, Trump is quite thin-skinned. He will inevitably respond to any disapproval or disagreement by deriding his critic as a loser, stupid, fat, ugly, or poor. Obviously Trump considers wealth, success, and good looks to be of the highest importance. Trump's the king of ad hominem attacks. If he's in the televised Republican debates, his aggression and nastiness will entertain. But he won't go much further. Many Republicans simply don't like the man. If your base doesn't like you what do you do? Some of Trump's statements reveal an incredible ignorance of our political system. As both supporters and detractors of President Obama point out, the President can't just rule by fiat. A domineering personality will only get you so far. Once this reality starts to penetrate Trump's delusions about his popularity and applicable skill sets, the results won't be pretty. As mentioned, he doesn't handle rejection well. Rejection is for losers. If Trump is rejected then he will be a loser. But Trump can't be a loser. There could be a mental breakdown looming here folks.
George Pataki
Actually he really can't. Seriously are there Republican voters in the South, in the Midwest, in the West who are fiending for their Pataki fix? If there are, so far the polls haven't shown it. But you know people initially laughed at Clinton and Reagan. So you never know. Pataki is a polished but not exciting public speaker. He could inject some gravitas into the race. If he can win in the early Northeast primaries simply by not being a gaffe machine and showing contrast to the more exciting but unelectable hard right candidates, Pataki might hang around longer than some rivals would like. If that happens well I guess anything is theoretically possible. A flipped coin can land on its edge after all.
Why he can't win
Who is he? Has anyone outside of New York heard of this fellow? When I think of New York politicians I think of Rudy Giuliani, Anthony Weiner, Andrew Cuomo, Bill DeBlasio, Michael Bloomberg and Elliot Spitzer (who's in real estate now). I knew Pataki was a former governor but I was unfamiliar with his record. However one thing I did know is that Pataki is pro-choice. He's also not looking to fight to the last conservative in order to stop gay marriage. He says leave it to the states. Let that marinate for a second. That means that the Southern and Midwestern social conservatives would just not vote for him once they know his stance. They think they've compromised enough already by voting for McCain and Romney, whom they saw as wobbly on those issues. There are simply not enough pro-choice primary voting Republicans in existence to give Pataki the nomination.
Lindsey Graham
Why he can win
From the amount of media coverage that Senator Graham obtains with his constant and genially deranged neo-colonial pronouncements on foreign policy you would think that he's the majority leader of the Senate or some sort of special envoy. He's neither. But he can point to a number of foreign policy reversals, setbacks and a few mistakes which the Obama Administration has made or experienced. Graham will claim that he predicted them (even if he didn't) and try to brand himself as a military man who has the foresight and toughness to stand by America's friends and against America's enemies. It's a longshot because Presidents don't often win or lose the job based on foreign policy concerns. But if you don't have the guts to take a chance, don't run for President. If you're concerned about ISIS, if you think Russia and China have been getting too big for their britches, if you think that the US needs to increase military spending, then Graham's your man. Graham will look to take on and take down Senator Rand Paul.
Why he can't win
Graham is unmarried and childless without many (any?) publicly known former girlfriends. He's been derided as pro-amnesty. Either stance alone is politically challenging for someone trying to woo an aggressively pro-natal and occasionally xenophobic Republican base. Together, they make it almost impossible for him to win. The idea of immigration reform that gives legal status or citizenship to illegal immigrants is a non-starter to many Republican primary voters. The perception held by some people across the political spectrum is that Graham is closeted. It's difficult for a single man to become President. Fellow Republicans are already making fun of Graham for his lack of female companionship. Graham himself is evidently worried about these rumors. He's giving interviews talking about his past girlfriends and being pictured doing "manly" things like shooting pool. It's not fair. Graham's personal life is no one's business but public figures must accept a certain intrusiveness. Ask Gary Hart. Joking that white men in male only clubs would do great in his presidency was not a good move. Graham should win or lose on the issues but often elections are just like high school redux. The other reason Graham can't win is that judging by some past statements he would take the United States to war against, well just about everyone. The goofy grin and genteel accent won't help him sell more foreign interventions to voters.
Jeb Bush
Why he can win
The man dropped a significant amount of weight in a short period of time. He doesn't look portly any more. So there's that. Also although he is by any reasonable standard a man of the right, he's not (at least publicly) talking about the Obama Administration's secret plans to decrease the percentage of white voters or invade Texas or turn everyone Muslim. So Jeb Bush is electable. At least he would be if he can make it past the primary gauntlet. All he has to do is be just right enough to steal away enough primary voters to win and then remain slightly to the right of Hillary Clinton in the general election.
Why he can't win
Plenty of Republican voters and political handlers have not really forgiven Jeb's brother for making the Republican brand so toxic that Barack Obama won election twice. That still hurts. Another Bush on the ticket will bring back all of the previous bad feelings (and jokes) about George Bush's incompetence and cluelessness. Also like Hillary Clinton, Jeb Bush will struggle a bit to let voters know exactly why he should be President. Why does he want to be President? Does he really want to be President or does he just think it's expected of him. How does he differentiate himself from his brother and father without seeming to be disloyal or slick? How do you criticize family publicly or respond to other people making such criticism. His campaign's recent invocation of Pickett's Charge as a model for his political struggle going forward was telling. Leaving aside the distastefulness of giving a shoutout to a Confederate general, Pickett's Charge was a poorly conceived, poorly planned and ultimately disastrous maneuver that destroyed Pickett's division and was later studied as a model of what not to do. Is that how Bush or his allies see his campaign? Interesting. Bush is also considered a moderate within Republican circles. He's not a guy who's screaming invective at illegal immigrants. He's establishment. I don't think this will help in the Republican primary field where there is a seething hatred towards establishment Republicans who have after all, lost twice to the black guy.
Martin O'Malley
Lincoln Chaffee
Why they can win
They can't.
Why they can't win
These two guys are the mini-me's of the Democratic primary season. I'm not yet convinced that Clinton didn't entice them into the race just to give the whiff of actual competition. They're the sparring partners. All they are supposed to do is give the fighter a work out, make sure she's sharp and task her a little bit but that's it. Doing serious damage or God forbid, winning, is not on the agenda. Much like Chuck Wepner did against Ali, they might go the distance or even knock Hillary down but at the end of the day neither one of them will win. Although each man will run to the left of Hillary, their records show a similar dedication to the same sort of bland corporatism which Hillary represents.
Rick Perry
Why he can win
There are three reasons that Rick Perry can win in 2016. (1) He's healthy and prepared this time. (2) He looks Presidential, and that's half the battle. (3) I forgot. Seriously though Perry could be the breakthrough candidate who can, a la Saint Ronald Reagan, bring together most of the Republican feuding tribes. He can make a good play for the evangelical voters. He can speak to the pro-military/neo-conservative folk. He's got his share of the big business crowd. As former governor of Texas almost by definition Perry can be competitive with the law-and-order caucus. He could even appeal to some libertarians by dint of Texas' relatively light regulatory touch. As a son of the South with the accent to prove it he will have appeal to that region's social conservatives. He was one of the few Republican candidates in the 2012 primary season who wasn't calling for immediate public executions of illegal immigrants. So if he can get through the primaries he could be that rare hard right candidate who has just enough of the human touch to win over a few swing states. Difficult but not impossible.
Why he can't win
Just kidding. Been there, done that. There's a saying that you never get a second chance to make a first impression. It will be difficult for Perry to reverse the belief that he's just another bellicose Texas lightweight who's eager to shoot from the hip but has no idea what he's talking about. His current poll numbers seem to suggest that Republican voters have kicked the tires, looked inside the hood and moved on.
Rick Santorum
Why he can win
2016 could see a massive change in the electorate. Out of nowhere voters will suddenly demand that their President be anti-evolution, anti-gay marriage, anti-contraception and pro-life with few if any exceptions. They will want a President who criticizes the Pope. It's time for Santorum! He's also no "free-trade" fundamentalist . If he can tone down his emphasis on social issues, he could have some appeal to working class voters who are not scared s***less about gays.
Why he can't win
The field is not big enough to hold multiple people who want to tout their fidelity to a particular interpretation of a faith tradition as primary proof of their fitness to be President. Huckabee, Cruz, Perry and Carson as well as a few undeclared candidates will all be appealing to the same subset of voters as Santorum. When there is that much competition you need to stand out and shine. You also need to have some pretty sharp elbows. Santorum has the second trait but I'm not so sure about the first. His sharp emphasis on social issues means that he can't help but take positions on gender and sexual questions that are easily caricatured by the media and a future Democratic opponent. Ultimately people don't want to elect a President who is a moral scold.
