If I was Jeb Bush and I wanted to be elected President in 2016, here's a little advice from a political junkie.
This entire strategy assumes that Hillary will be the Democratic nominee. I think that's a pretty safe bet.
First, you've got to win the primary. I'll assume that fundraising won't be an issue. You're a Bush.
I would cloak my overall primary and presidential run in terms of an "underdog revenge match" from 1992 (Bill Clinton beating Bush Sr.). This will give you an instant, easy go-to pitch that you "belong" in the race. Not only is it accurate and a great story-line, but it places you in the envious role of "underdog." This way you don't appear to be the privileged candidate who arrogantly assumes they'll be ordained. You can use this line of tripe to preemptively attack Hillary down the road. Also, it puts you on the same level as Hillary, thus distancing yourself from a potentially hotly contested primary. Perception is everything. Hell, look how Obama defied the conventional norms. He basically came out of nowhere. But I'm getting ahead of myself.
Make a firm commitment to a comprehensive, national, cable news strategy. Screw the idea of spending an entire year in Iowa pandering to all these small town mayors, pastors and city councilmen. Every twinkie bake off, every church raffle, every county fair... Iowa's pretty fucked up anyway (lots of creationists hooked on oxycontin). Look who won last time around - Santorum & Bachmann? All you need to do is place somewhere near the top. Then lightly downplay the importance of Iowa. Spin the hell out of it - you're already on the campaign bus headed to NH, SC and Florida. Try to marginalize Iowa. Jeb will play well in the next 3 states and roll from there. By then, you're on the fast track.
Never shy away from the press at any point. Never go into hiding or seclusion. Go on MSNBC, Al Jazeera, CNN, BBC - all of them, not just Fox News. Take a page out of John McCain straight talk-express in 2000. The news cycle is 24/7 - inclusive and continuous. Assemble a professional, younger, real-time war room who live, eat and breathe high stakes politics.
Stay true to yourself. Don't get a far-right makeover.
I'd let the other candidates beat each other up while trying to stay on the sidelines and appear presidential. Kind of like what Romney did in 2012. Romney actually did a decent job of this... well, until he tried to place a $10,000 bet with Rick Perry during a nationally televised debate. Romney was a totally flawed candidate anyway (friendly personality, but totally out of touch with mainstream America - this kind of stuff happens when you're a conservative Mormon worth a quarter billion). And he put together a very cautious and uninspired team (for the national stage). And even with all those knocks, it was still a relatively tight race.
As I was saying, let the other candidates extinguish themselves. Fox News will try that same spin they used in the 2012 primary. Giving every candidate their day-in-the-sun/top-of-the-polls ranking in order to prove that ALL of them are realistically viable candidates. I seem to be the only one in the U.S. that understood this concept. I salute the Fox Network on this move. It was very well played. But all of them self-imploded anyway (Cain - affair/no substance, Santorum - religious zealot, Bachmann - bizarre imbecile, Pawlenty - boring, Perry - dolt, Gingrich - self righteous, wife wasn't technically a human being, etc.).
Let Rand Paul be a fringe, conspiracy guy. Not suited for high office.
Let Christie be the obnoxious blowhard, non-statesmanlike.
Let Cruz be the zany, right wing extremist.
Let Rubio be too young and inexperienced. Not ready for the national stage. But don't tear him down. He's a good fit for VP.
The most important thing - stay ABOVE the fray and pray that Gingrich doesn't run as a means of promoting his own agenda ($ and personal fame). If you get on his bad side, he'll make you look like an idiot. This is Jeb's achilles heel - being portrayed as the mental equivalent of his brother.
Now let's assume you've won the hotly contested primary.
Here's how you win in the general. Obviously, you'll need to pivot to the center. That's the "sage" advice you'll get from your overpaid, political consultants. You'll need Independents, women and a strategy for making a reasonable dent in the minority vote. You'll have to carry this number of electoral votes in this number of swing states. Brilliant! Yeah right! Who would've thought?
Okay... the best case scenario would be to hope someone famous, with plenty of cash runs from the left (maybe Oprah or a popular movie star) as an independent. Totally screws Hillary out of 5-10% of her popular vote and you manage to sneak in. Similar to how Ross Perot siphoned votes from Bush in 1992. That likely will not happen... so you'll need a real strategy.
Now here's what we know. Everyone right now is totally hatin' on the government - the partisanship, the shady dealings, the corruption, the girth, the beltway, the gridlock, the bureaucracy, the taxes, the spending, the invasion of privacy, everything. This narrative appeals to everyone. You need to let everything ride on this premise. How you're the only candidate that is completely committed to not falling into the trap of dysfunctional, big government. You are NOT part of the establishment. Since you're coming from the "governor of Florida" perspective, this can work.
The problem is you'll need to PROVE it. You'll need to prove that YOU are the true outsider. A very difficult task since your brother presided over the United Church of America for 8 years. And your father headed the CIA, was Vice President for 8 years and oh yeah... President for 4 years. So here's how you actually do it.
Here's my idea. Explain to the American people how hubris has negatively impacted the 2 prior administrations. Throw both of them under the bus. This sucks because you'll have to sell out your brother George, but at the same time, it's a good move because you also distance yourself from him. It happened with George Bush's "you're with us or against us" war on terror. And the same hubris phenomenon happened with the Obama team on healthcare. Explain how when an administration gets something big accomplished, they quickly become a victim of the "inside the bubble" thinking. The cronyism and ideological insiders seemingly take over everything --- positioning and policy. Explain how this happened to BOTH prior administrations. Just because you accomplish something major, doesn't mean you can blow off the concerns of the other party. You were elected to govern. You know this. You're the President, not a King. This whole concept will sell to mainstream America.
You'll take that different approach. You'll keep the cabinet fresh and encourage dissent. You'll be receptive to ideas from the opposition party and inclusive when it comes to major policy decisions. You'll be a President for the entire U.S. - you could do this by getting some photo ops of campaigning in very solid RED states. Places like Huntsville, Alabama or Kansas or whatever. Places where you're confidently ahead. And go straight into Hillary land as well (Albany and NYC). While Hillary is totally committed to Hollywood, DC, NYC and the swing states, you're the one who truly understands how the country needs an all-inclusive President. USE THE NATIONAL PLATFORM OF CABLE TELEVISION. I realize it defies conventional wisdom, but your time might be better spent in South Dakota as opposed to Toledo, Ohio. You're the one who's taking a national approach. Perception is everything. You'll bring a different style of governing - something only a governor could understand (not Hillary who is the consummate political establishment insider - 8 years in the White House, New York Senator and Secretary of State). If she tries to latch onto this strategy, she'll appear to be conniving. Even better, it would force Hillary to take the opposite route (politics of divisiveness). And just what happens when a woman goes on the attack??? Last time I checked, they come across as a bitch. That's the trap Hillary needs to avoid. So why not set her up for it?
Jeb would dictate the terms, establish the narrative and the playing field. Hillary would have a hell of a fight on her hands if you go this route. Because she'll have to go with the opposite old-school political strategy. She'll have to play the tactics of divide and conquer (social issues, women's rights, abortion, gay marriage, etc.) Division doesn't work as well when you're a woman - because... well once again, you get labeled as a bitch.
Remember, Jeb needs to appear like a statesman but with a twist - having a mild contempt for govt. An establishment, stalwart candidate like Hillary would look silly if she tried something like this. She's about as crafty and resourceful as they come... but she'd find herself on the defensive. That's the perspective you want her stuck in. You define the terms. You define the narrative.
Some other miscellaneous points...
Don't get trapped in the stale anti-Obama rhetoric (birther crap, Bengazi, Solendra, etc.). This stuff won't sell in the general. You've got to keep an eye on the future, not the past. You're supposed to be that candidate who's looking "forward." And if you see Sarah Palin or Rush Limbaugh, run in the opposite direction. Steer clear of the Tea Party, religious right as best you can. They're all anti-Hillary anyway. Trust me, the base will be energized solely based on their contempt for the Hill-dog. You've already got their votes.
No Romney "America the Beautiful" singalongs and pledge of allegiance crap. Most normal people know that it's a blatant attempt at pandering. Once again, be yourself. The worst thing you can do is appear like another wealthy phony. No car elevators, no Olympic horses, no fake hunting photo ops. These days, the vast majority of voters know it's all bullshit anyway. Plus, it makes you fodder for the late night comedians.
(Probably the best, high stakes political commercial int he history of presidential elections).
In that same vain, let it discreetly leak that you have no interest in actively seeking an endorsement from Donald Trump. He can endorse me if he wants. If he doesn't, that's fine. Jokingly comment and brush it off -- "I'll just have to find a way to live with myself." Even better yet, comically inform the press, "Well if Trump doesn't endorse me, I should seriously consider dropping out of the race." Humor is powerful. Showcase your personality. Jeb can do this. From what I've seen, he's a folksy intellectual. Smart like his father. Friendly like his brother. Comfortable like his mother. He brings the best of his family traits.
The big thing is that you'll need a strategy to reach out to Independents and women. Minorities will be an uphill battle, but I think you can snag some of the Latino vote if you stick Rubio as your VP. Let him do the dirty work (anti-abortion and anti-gay marriage). You'll need to stay above the pettiness. I know, with Rubio it's the two guys from Florida narrative. But people can get past this. The old strategy of geographically balancing the ticket is way-outdated. Plus, winning Florida is a must.
Maybe try and find a way to bring Colin Powell back into the picture. You need to bring in some "power brokers" that are moderates. Look outside the government. Look to the media, big business, maybe a sports legend or something.
Personally, I think Hillary will win. She's the superior politician and the timing seems right for a woman President. But you never know. Say if the stampedes happen --- all bets are off. A national crisis can change everything. Conventional wisdom goes straight out the window. But all things remaining equal, I think Hillary is elected President in 2016. She's got my vote. Even though I wrote this blog, you gotta love her. She's such a total bad ass!
And I just came up with her campaign slogan.