The Truth About Jeb Bush’s Presidential Ambitions

There are currently two factions in American presidential politics: Those who are absolutely sure Jeb Bush will run for president in 2016 and those who are absolutely sure he won’t.

The first group points to Bush’s recent weeks on the road—he hit a variety of long-planned Republican political and policy events in advance of the midterms, and put on an impressively lively and incisive show. Supporters share stories of Bush aides quietly urging potential backers to keep their powder dry only a little longer. George W. Bush’s jaunty recent assertion that his brother “is weighing his options,” is seen as a trilling dog whistle signifying that Dallas, Houston, and, significantly, Kennebunkport are all on board for a third Bush presidency.

The second group, meanwhile, insists Jeb Bush will once again sit out the presidential race, this time scared off by the lethal-looking twin buzz saws of Common Core and immigration. Even more lethal, there are enduring murmurs that Jeb’s irrepressibly formidable mother, his wife, and his daughter are dead set against a run. Members of Group Two clock the echoing absence of the courtship of aggressive bundlers; interest-group activists; and Iowa, New Hampshire, and South Carolina kingmakers; and conclude that there is no candidacy brewing—just a guy with a great résumé, a substantive agenda, and a brand name, stirring the pot.

Such mirror-image speculation is only mounting—in the last week alone, three premium-grade Republican sources confided to me with utmost certainty that Bush is in fact already running, while one of America’s premier political reporters privately offered up a laundry list of reasons why Bush was definitively not taking the plunge.

Here’s the reality, distilled from over a dozen discussions with those who know Bush really well: Jeb himself still hasn’t decided.

There is no doubt that Bush is significantly closer to running for President than he was four years ago. He isn’t showing some leg to sell books or raise his speaking fees. He isn’t worried about the mechanics of the race, such as who might be his New Hampshire campaign manager, or how best to deal with straw polls. His decision-making process is less about consultation than, as is typical for the former Florida governor, about introspection. Jeb Bush is grappling with the hardest of questions: Is he the right person to bring the Republican Party toward the center and govern a country that has proven stubbornly difficult to lead? In other words, is this, finally, his time?

A potential Jeb Bush candidacy is a high-stakes question.

Since the Reagan years, nearly every Republican Party presidential nominee has been the establishment favorite, raised the most money in the year before the election, and has been viewed by the Gang of 500 as the most formidable general election candidate. (The one exception: In 1996, Phil Gramm took in slightly more cash than Bob Dole, and Bill Clinton’s team worried more about competing head-to-head with Lamar Alexander than they did the Bobster.)

There is uncharacteristic chaos right now in the Republican Party, which, for the first time in the modern era, is lacking a clear frontrunner at this stage of the presidential cycle. Given Hillary Clinton’s strength and the GOP’s complete failure since 2012 to improve its standing with the key elements of the Obama coalition of the ascendant—Hispanics, young voters, single women—the establishment is on the verge of a post-midterm panic about the unfilled vacuum. Not one GOP sharpie I’ve talked to in the past six months has said with any confidence who their nominee will be, and most are either stumped or limp-throated when asked to venture a guess at the top tier. Pressed, they’ll typically cough up Chris Christie, Paul Ryan, Marco Rubio, Rand Paul, and Mitt Romney. A portion of that bunch would likely not get in the race if Bush decides to run. None of them combines Bush’s fundraising capacity and his compelling case for general-election strength.

Until and unless grandmotherhood and other personal factors keep the Democratic frontrunner out of the contest, Republicans have to assume they are looking for a nominee who can take on a supremely daunting, uber-iconic Clinton.

While supporters of flashy candidates such as Paul and Rubio talk a good game about nomination muscle, national appeal, and anti-Clinton clout, Bush has walked the walk as the popular governor of electorally indispensable Florida and as a member of the most politically successful family in American history. Jeb (along with Romney) is likely the only contestant who could keep pace with the expected Clinton haul in excess of $1.5 billion. “The Republican donor base will fall in line” behind Bush, says one of the party’s best and most experienced fundraisers. “There is no competition.”

Despite a near-total lack of spadework in the early states and among activists and bundlers, Bush could line up a team of campaign staffers, policy experts, and finance mavens at a moment’s notice. More to the point, he doesn’t have much ground to make up. One long-time senior Republican official says of the other prospects, “None of them has done shit” to build an organization so far. “Bush will have the band put together in a day. He is the most prepared from a infrastructure point of view by light-years.” Unlike his competitors, Bush could lure donors off the fence in a hurry, without undergoing a hazing trial to test skill and stability. The train would fire up and chug away from the station at the git-go.

Moving to the Electoral College endgame and the essentials of demography and partisan affiliation, Bush’s strength is manifest. His long record attracting non-white voters, especially Hispanics, stands out. This is hugely important, given the reality that promoting a path to citizenship has become a litmus test for many in the Latino community—and while some GOPers may still be in denial about the arithmetic, the party can’t win back the White House without garnering a much larger share of the Hispanic vote than Romney won.

It is also striking how many Democrats who have met Jeb Bush tell me they’ve come away both impressed and open to supporting him for president, a crossover capacity that is a rarity in this polarized nation of ours. And Bush would be without peer in fending off Hillary Clinton’s ability to encroach on elite Republican patronage, including Wall Streeters.

Finally, the most macro significant question for any Republican putting him or herself forward to beat Clinton is this: What states can you win that Romney lost? For Bush, the easy answer includes Florida, Ohio, Colorado, Iowa, Wisconsin, New Hampshire, and Virginia. If he runs a strong campaign, Bush could also compete in California and possibly New Jersey and Michigan.

Speaker John Boehner tried hard to get Bush in the race last time, putting on extra pressure in February of 2012, when Romney appeared in danger of losing to, or being politically crippled by, Rick Santorum. Twice in the last two weeks, Boehner has again made his yearning for the Floridian publicly clear. There are other politicians, including several prominent senators and even a high-profile would-be presidential candidate, who are said to have assured Jeb that they would cheerfully back him were he to run.

Within JebWorld, which prefers operating on its own tweaked-Swiss-watch schedule, there is a bit of frustration with both the “he’s running!” and the “he’s not running!” brigades. Bush’s political inner-inner circle is a bicoastal two-person shop made up of Californian Mike Murphy and Floridian Sally Bradshaw, both of whom have advised him about politics and policy for more than two decades. The members of the next tier, Bush’s outer-inner circle, would fill the seats of a Broadway theater. It includes bundlers, business people, think tankers, pols, strategists, and friends, all of whom are super eager to see Bush run. They agree with the governor’s own humble assessment that he is a special leader who can wait until early 2015 to enter the race, even from the standing start it would effectively involve. That Jeb would aim for a far less traditional campaign than previous Republican nominees. That as a candidate and president, he would emphasize the same issues that have been his passion in and out of government throughout his decades-long career: fiscal discipline, education, the efficient delivery of government services (including health care), and equal opportunity.

But don’t dig up that ‘90s vintage Bush v. Clinton memorabilia just yet.

Despite support of enthusiastic donors, establishment leaders, voters, and even some reporters (many of whom have been granted access to his private email address), Jeb has two-ton problems, from blue-blooded Bush fatigue and the reverberations of his brother’s Oval choices to his own grassroots shortcomings and mild, spare-to-the-heir reputation. Not to mention weak polling data and a meek social media presence—all of which would factor into the looming dust-ups of Iowa and New Hampshire and the muck of the Freak Show. Says one observer, “It would be a very tough slog. Part of it is the Bush name,” but also some apostate positions and a sense that Bush has been out of elective politics for too long and has a demeanor more suited for the American Enterprise Institute than Greenville, SC.

While immigration is often cited as Bush’s biggest problem with the conservative base, his support for the education standards in the Common Core has actually caused more trouble this year, inciting heckling protests outside some events and grumbling inside the party. With his education advisers, Bush has regular conversations about the issue. Some of his aides have attempted to understand why the matter provokes so much grassroots anger and have talked about trying to reframe his position to express support of higher standards, although it’s a fight Bush would welcome as a presidential candidate. In private meetings, when pressed on both the substance and the politics, Bush pushes back hard.

Then there’s the persistent chatter that three generation of Bush women don’t want any part of another White House run. Barbara’s icy dismissals of a Candidate Jeb (“we’ve had enough Bushes”) have made both national news and late-night laugh fodder. One source, however, who recently spent time with the former first lady says, in fact, she has shifted from unalterably opposed to “neutral,” in part because of how much her ailing husband wants to see their son in the Oval Office. (A spokesman for former President Bush 41 and Mrs. Bush, Jim McGrath, says, her tart comments shrugging off a Jeb candidacy were “about there being no sense of entitlement. She said countless times that Jeb would make a superb president. Nothing has changed.”)

Barbara Bush’s previous skepticism, according to numerous sources, was grounded in concern that daughter-in-law Columba Bush would not take well to the harsh spotlight of either a coast-to-coast campaign or life in Washington. Jeb’s wife is said to be shy, private, and sensitive to ridicule she received for struggling to transition from her native Spanish to English. But lately Columba has inched closer to the spotlight, participating in a few public events and in family activities in Kennebunkport, providing some reassurance to those closest to Jeb. Columba has been traveling with her husband on some international trips, attended at least one board dinner with him in New York this year, and, according to an intimate, has been more actively engaged in her husband’s public policy work in the last 12 months than she has been in five or six years.

“She’s seen it all,” says a family friend. “The good, the bad, and the ugly. I don’t think she’s capable of doing ten [presidential campaign] events a day. But she could do a couple.”

Their two sons, Jeb Jr. and George P., are both willing to go along for the ride if their father runs, Bush intimates say. Daughter Noelle, 37, has a history of drug abuse but is said to be in a “good place” now, given her past, and, somewhat regularly travels from her home in Orlando to visit her parents in south Florida. Jeb Bush presumably wouldn’t be as far along in his consideration if Noelle’s condition or posture made running a non-starter.

To paraphrase a favorite Bill Clinton line, if Republicans want a perfect candidate, they can vote for someone else. If he runs, Jeb’s central challenges are very similar to Hillary’s, although she would have a much better chance of avoiding a bruising nomination fight. They would both have to convince the country that, familiar family name notwithstanding, they represent change, fresh ideas, and a new direction.

One Republican—fairly panting for a Jeb candidacy—says, “He believes that he can convince people what the Republican Party stands for and what it can do on behalf of the American people.” The White House is probably the best place to wield that kind of influence, which is why so many members of his outer-inner circle insist the vector is facing toward yes. Says one close friend, “He’s getting there. He’s working himself into it.”

But another Republican big shot who has attended recent events with Bush posits that the current swell could be more about Bush’s followers than Bush himself. “The ever-hopeful chattering class thinks they need him to run. He does five events. He’s doing what Jeb Bush does well. He’s very focused and doing his thing. And trying to figure out if he can do this on a national scale.”

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