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Jeb Bush starts to develop the wrong kind of reputation

How many more gaffes will Jeb Bush have to make before the intra-party whispers begin in earnest?
Jeb Bush
Republican presidential candidate, former Florida Gov. Jeb Bush waits in a hallway after a campaign event Saturday, June 27, 2015, in Henderson, Nev.
Yesterday afternoon, Jeb Bush was eager to bash Planned Parenthood for reasons he couldn't quite explain. It led the Republican presidential hopeful to say, unprompted, "I'm not sure we need half a billion dollars for women's health issues."
The Weekly Standard's John McCormack, a conservative writer, asked the question on the minds of many:

"Isn't one benefit of an establishment candidate supposed to be that he's not going to make gaffes like this?"

It's a safe bet McCormack wasn't the only conservative asking. Some verbal slip-ups are inevitable for anyone whose public comments are under close scrutiny, and every candidate in both parties will make comments over the course of the campaign that they'll wish they worded differently.
That said, Jeb Bush, who entered the race with a reputation for wonky precision and depth of knowledge, is quickly cultivating a very different kind of caricature -- one that's far less flattering.
For example, Bush recently said he wants to "phase out" Medicare, adding soon after that he didn't really mean it. (The former governor wants to replace Medicare with a voucher system, which he now believes is totally different from "phasing out" the existing Medicare system.)
Bush also said he wants Americans to "work longer hours," only to say he didn't quite mean that, either. After the Charleston massacre, he said, "I don't know what was on the mind or the heart of the man who committed these atrocious crimes," even though the racist motivation was obvious, and aides quickly had to clarify these comments, too. When he tried to talk about ISIS and clumsily got the relevant details wrong,  campaign aides scrambled to clarify once more.
Asked in the spring about his position on the war in Iraq, the Florida Republican gave four different answers over the course of four days, prompting Gail Collins to write, "Wow, Jeb Bush is awful."
And really, these are just some of the more important examples. Jeb has also gotten the retirement age wrong while talking about Social Security; he's complained about President Obama using "big-syllable words"; and he's argued the U.S. economy hasn't improved since the 2008 crisis.
Sure, it's August 2015, and the election is still over a year away. It stands to reason that a former governor -- who hasn't run for elected office since 2002 -- will be rusty as he figures out how to be a national candidate.
But for Republican insiders, who have quite a bit invested -- literally and figuratively -- in Bush, there's not only an expectation that he's supposed to be sharp already, there's also the inconvenient fact that he doesn't seem to be improving.
How many more gaffes before the intra-party whispers begin in earnest?