Everyday there's someone else announcing his candidacy because he thinks he has what it takes to be President of the United States. I really do believe that one possible reason for this number of candidates is because some people think that if the black guy could do it how hard could it really be. I'm not 100% serious writing that. Not completely anyway. But for all the myriad disagreements I have and will continue to have with President Obama it is still in some aspects pretty amazing that the twice elected President of United States is a black man with a name that is utterly non-European. That's a big deal. And it is also a big deal that America might follow the election of the first black President with the election of the first female President. But on the Republican side because there is no incumbent to follow or obvious heir, much like GRRM's War of The Five Kings, people think why not me? That HAS to be the justification for long shot mopes like Bobby Jindal, George Pataki or Ben Carson, to name a few. It's like the lottery. Someone has to win. And you can't win if you don't play. And even if you lose you may not have to return all of the campaign contributions. You could parlay your new fame into a television or radio show. Perhaps you have a book you'd like to peddle.Or maybe you intend to be the loyal opposition/sparring mate for whoever eventually does win. Then you can get a cushy cabinet position in their administration. Then you just kick back and do favors for lobbyists for three or four years before cashing in your chips and becoming a lobbyist or tripling your salary at a think tank. On the other hand if you really are trying to win the race there are different paths to victory for candidates, especially Republican ones, in an America with a browning electorate. Some Republican nominees would attempt to run up the score with white voters, particularly among the hard right base. Other Republicans would seek to placate the base but reach out to white suburban college educated voters of whatever political background who may not have seething rage about illegal immigration or gay marriage but who are still worried about their children's economic prospects. And some Democrats might point to the party's dismal national standing among white men, especially Southern white men, and claim that they can reverse that to build a new broad based coalition. I don't know and neither does anyone else who will win their party nominations and ultimately the Presidency or which argument will resonate most strongly with the voters. I do know that this race is going to be wide open, perhaps a little more on the Republican than the Democratic side, though Sanders is currently showing a little more strength and staying power than Clinton would probably like to see.
Why he can win
The governor of Wisconsin could be the Republican Prince Who Was Promised. With the possible exception of New York City is there a region or area that is more closely associated with unions than the upper Midwest? I'm not sure that there is. The Midwest is where the modern labor movement was born and where it thrived for years. And yet, times change. Governor Scott Walker emasculated and humiliated public sector unions on their home turf. He beat them. He survived recall and was elected again despite the best effort of unions and sympathetic supporters. He took their best shot and is still standing. Unions are on the run. Walker's not stopping to rest on his laurels. He's going after tenure as well. His status as a college dropout may well endear him to some people who feel that overeducated Ivy League pointy headed elites are ruining America. There's no word as to whether this "aw shucks we's jus regular folk" schtick interferes with Walker's fealty to the MIT educated Koch Brothers. I'm guessing not. But in any event Walker greatly appeals to the "let them eat cake" cheap labor camp of the Republican capitalist class as well as to the resentful Republican proletariat who are often overcome with schadenfreude anytime a government worker loses his or her job, must take a lower salary or loses union rights. There was some data in the 2012 election that suggested that voter turnout in the Midwest among white conservatives was lower than expected. If Walker could reverse that he might make a few Midwest states besides Indiana turn red. And then it's anyone's ball game isn't it?
Why he can't win
Although he has started to walk the walk, as witnessed by his recent signing of the 20 week abortion ban, it's not really clear that Walker has always talked the talk around social issues which are dear to the hearts of conservatives, particularly in and around the Bible belt. On the issue of illegal immigration in particular he is a late convert. Some social conservatives feel used by the Republican establishment that whispers sweet nothings to them to get the vote but is really only interested in delivering things like low taxes and low regulation for their business class. Can Walker change any perception that he only cares about gutting unions?
Why he can win
Webb is a throwback to years when the white vote, particularly the white male vote, was more up for grabs in Presidential elections than it is now. The world has changed however. In Presidential elections, Republicans routinely get 60%+ of white voters nationwide and much more in the South. But as we have seen that proportion is no longer enough to win the Presidential election. This has caused some internecine strife among Republicans. Some just want to ignore this and keep the same messaging. Others want to change messaging, if not policy, and try to woo away some winnable elements of the Democratic coalition. Others want to go full white nationalist and try to increase their percentage of the white vote, which is still by far the largest group in America. This Republican problem, viewed with much glee by some Democrats, also leaves other more conservative Democrats in a bind. But Webb may see this as an opportunity. If he attracts conservative/independent whites who are more interested in class and pocketbook issues than they are in ensuring that whoever makes the latest racist gaffe is suitably humiliated and shunned, then he can stop the Democratic losses among whites in Presidential elections. There is a nascent class consciousness among many working class white Southerners which usually loses to race consciousness. Webb could bridge this. Perhaps he can even win more than one or two Southern states. He's a combat vet, something fewer and fewer Presidential candidates are. And he wasn't just twiddling his thumbs. Webb put in work. He's got a Navy Cross, Bronze Stars, Purple Hearts and a Silver Star. He possesses foreign policy experience at higher levels as well, having served as Secretary of the Navy and Assistant Secretary of Defense.
Why he can't win
Yeah. I was just kidding. His run is just an exercise in self-indulgence. He's to the right of where the Democratic Party base is moving. Many of his most logical and likely supporters have probably identified as Republican or independent for years. It will be a heavy lift for both policy and identity politics reasons for Webb to make successful inroads with many Democratic primary voters. Although I understand his attempt to find nuance around Confederate Flag displays, again the people who would support him most passionately are already Republicans.
Why he can win
He's the other Republican governor from the Midwest running for President. He's managed to combine pragmatic conservatism with what he sees as good policy decisions to attract widespread support in his state. He won't easily be characterized as a mouth breathing goober who gets all of his information from AM radio. Like Walker, Kasich, would if nominated, try to provide a path to victory for the GOP through the upper Midwest, which has not yet undergone the demographic transformations which have turned Florida, Virginia and North Carolina into battleground states and placed California firmly out of reach. If the GOP can win Ohio it makes the electoral math much easier. Kasich's seeming reasonableness could entice some independents to vote for him, particularly if the Democratic candidate is lackluster.
Why he can't win
I was always told that if you graduated from Ohio State University it is a miracle that you manage to tie your shoes every morning let alone run for President. Ok, that's probably not a fair, accurate or nice statement, though I still would check to see if Kasich is wearing loafers. Kasich's problem is not that he hails from that state down south but that conservative as he is, he's not going to be conservative enough for the Republican base. Kasich expanded Medicaid in Ohio under Obamacare and has also supported Common Core standards. If he ever starts to get any traction in this crowded Republican field you can be sure his rivals will tell everyone about his positions. And that is when Republican voters across the nation will see that Kasich has a bit of a quick temper. Now if you aim your ire at the normal Republican targets, media, minorities, welfare recipients, etc. all will be well and good. But if you're questioning the morality of Republican opposition to Obamacare and calling opponents stupid, I'm not sure you get too far with that (unless you're Trump). Also the positions of moderate conservative and snarky sarcastic ill-tempered conservative are already held by Jeb Bush and Chris Christie. Kasich will have to take them (and obviously Trump) down, to get any sort of traction. Right now he's just a rounding error in the polls.