Before debate, Jeb Bush faces off with challenges of his own making and a new political environment

Former Florida Gov. Jeb Bush faces some large obstacles in his quest for the Republican presidential nomination. (Brian Snyder/Reuters)

CLEVELAND — Jeb Bush has come face to face in the days and weeks leading up to the first presidential debate with the challenges that lie between him and the Republican nomination.

The former Florida governor is facing two large obstacles. One is the type of politician that he is — and has always been — and how he wants to conduct his candidacy. The second is the political and media environment he faces, which is different from anything he’s ever experienced in his political life.

Bush has made a series of comments over the past weeks that can at best be characterized as careless. The latest came on Tuesday, when he said, “I’m not sure we need a half a billion dollars for women’s health issues.” He was referring specifically to Planned Parenthood and the $528 million the group received from federal and state taxpayer money in 2014, but the way Bush phrased his comment allowed Democrats to cast him as opposing government funding for women’s health in general.

“He’s got no problem giving billions of dollars away to superwealthy and powerful corporations, but I guess women’s health just isn’t a priority for him,” said former Secretary of State Hillary Clinton, the leading Democratic candidate.

Two weeks ago, Bush was describing how he wants to change Medicare to put it on firmer financial footing for those who will enter the system in the future. He said he wants to “phase out” the current program and “move to a new system.” And the well-oiled Democratic political message machine blasted Bush for the comment, implying that he wants to end Medicare entirely.

“Now you want to take it away? Why are you always attacking the seniors?” a woman yelled at Bush during a town hall meeting in Gorham, N.H., the day after he made the Medicare comment. Bush spokesman Tim Miller accused the woman of being a Democratic plant.

And in May, Bush stumbled in response to a question about whether he would have backed sending U.S. troops to Iraq if he knew then what we know now about there being no weapons of mass destruction there. “I would have,” he told Fox News. He later reversed course and said, “Knowing what we know now, I would have not engaged, I would have not gone into Iraq.”

Bush explained his initial answer by saying he didn’t want to discourage or dishonor those in the U.S. military who fought in Iraq or lost their lives and their families. But it took him several days to say that, a period in which he was mocked for being unwilling or unable to distance himself from his brother, former President George W. Bush, who made the decision to invade Iraq in 2003.

Bush and his aides have repeatedly protested that his words are being taken out of context or exaggerated beyond what they mean. There is truth to that, but in modern politics, language matters, as does understanding the way opponents can use your words against you. And the emerging pattern with Bush is one of a failure to carefully consider his words and the possible traps that wait on the other side of many doors that Bush goes charging through.

And Bush does barrel through them — it’s just the type of politician he is. And it’s often an asset, a strength.

He has always been willing and eager to engage with the public and the press. When he was governor of Florida from 1999 to 2007, he gave out his email address and regularly engaged the questions of perfect strangers. It was normal for him to talk casually with reporters at length off the cuff, said Steve Schale, a Democratic operative in Florida who oversaw President Obama’s two campaigns in the state.

“One thing I always admired was that Jeb was willing to say what he thought,” Schale said. “Unlike [current Florida Gov.] Rick Scott, he doesn’t hide behind talking points.”

Case in point: After the event in Gorham in late July, for example, I asked Bush if Democratic presidential candidate Martin O’Malley should have apologized for saying to a crowd of primarily African-American activists, “Black lives matter. White lives matter. All lives matter.”

Bush didn’t blink or hesitate, blurting out exactly what he thought.

“No, for crying out loud, no. I mean we’re so uptight and so politically correct now that you apologize for saying lives matter?” he said with a roll of his eyes.

A more calculating politician, even if he wanted to be so frank, would have begun his comments by saying he understood the sentiment that motivated the activists to boo O’Malley and then would have explained why he disagreed with them. Bush didn’t do that, and he hasn’t tried to qualify his comments.

Bush told me last month in San Francisco that he knows his style will sometimes create turbulence for him but that he is banking on voters seeing him for who he is over the long haul of a yearlong process.

“There are bumps in the road. I’ll make mistakes. I’m not perfect. I’m not pretending to be,” Bush said. “But I’m running a campaign that I hope will show the authenticity of why I’m running, and I’m running a campaign that gets me vulnerable. I’m outside my comfort zone.”

“I do press gaggles. There’s no roping off of the press,” he said, in a shot at Clinton, whose aides held a rope in front of reporters as she marched in a Fourth of July parade, in Gorham of all places. “I do what I think candidates have to do to show who they are.”

The problem is that Bush’s expectations for how the political process works may be Pollyanna-ish.

“Because he is so smart, I think he expects people to keep up and not play stupid political games,” said Rick Wilson, a Republican political operative from Florida. “He expects an honest intellectual conversation.”

One close Bush adviser admitted months ago that this might be a challenge for Bush, that he may be too hopeful that a presidential campaign can be a debate about ideas rather than the sort of no-rules cage match that politics has become. In this he may take after his father, former president George H.W. Bush, who had to be prodded to attack Michael Dukakis in the 1988 contest. The Bush adviser acknowledged that the second Bush son to seek the presidency may need similar prodding.

Bush’s instinct to try to remain above the fray was nowhere more in evidence than at last week’s National Urban League’s annual meeting in Fort Lauderdale, when he completely ignored an attack on him by Clinton from the same stage. Clinton tore into Bush during an address to the group, criticizing him for his Medicare comment and his opposition to raising the minimum wage, as well as his policies on college access and voting rights.

Bush spoke about two hours later to the same gathering and did not respond, focusing instead on touting his accomplishments in Florida. Bush spokesman Tim Miller said that responding to Clinton “was never contemplated,” that Bush wanted to “bring a message of unity,” and he faulted Clinton for taking “cheap shots.”

Wilson said that Bush’s vow to run a “joyful campaign” is likely part of why he wants to “hold off as long as he can” from back-and-forth exchanges with opponents.

“He knows that these things devolve into negative screaming matches,” Wilson said.

Perhaps most consequential is the fact that politics at the national level has changed quite a bit since Bush held elected office or ran a campaign. It is faster, more intense, more focused on personality, gaffes and superficial image, and even more reliant than in the past on sound bites and less on substance.

“The media environment was very different” when Bush was governor, Wilson said. “We’ve now got this social media outrage machine.”

In addition, Bush in Florida did not have rivals that were his equal. “He had this eight-year conversation with himself,” Schale said. Now, he is up against a field full of Republican rivals and is already being treated by Clinton as a likely opponent.

In San Francisco, I asked Bush if he’ll continue to follow his current approach, taking all questions and all comers as the campaign progresses and the intensity increases.

“Yeah, I will try,” he said. “It gets a little crazy sometimes with the press. Sometimes it gets a little overwhelming.”