1) Even though He's very conservative the base thinks He's too moderate
"He is too moderate for the Republican base," conservative commentator and former presidential candidate Pat Buchanan said last month, echoing one of the most frequently cited views by political pundits and media outlets about a potential Jeb Bush candidacy.
Perhaps that's why Bush has been on the offensive recently, offering up a case for electability in an interview with the Wall Street Journal in which he said Republicans must be willing to “lose the primary to win the general."
It's a typical argument: Electability (think: Jeb Bush, Chris Christie), not ideology (Rand Paul, Ted Cruz) is Republican's best chance at defeating Democrats. By staying close to the nation's political center, Republicans can remain viable in a general election.
Unfortunately for Bush, however, that didn't work so well for Sen. John McCain and Gov. Mitt Romney, the last two moderate Republican presidential candidates.
Which is why, according to at least one source, conservative leaders are ganging up to block Bush.
2) Immigration and Education
On two major issues in Washington, Bush is on the wrong side -- at least the wrong side of his base.
His views on immigration in particular have made some in his party recoil.As the Washington Post points out, he doesn't just support comprehensive immigration reform – for which he bears a scarlet letter 'I' in his party -– he has spoken sympathetically about undocumented immigrants.
In a speech in April, Bush said, “Yes, they broke the law, but it’s not a felony. It’s an act of love, it’s an act of commitment to your family.”
The last time a Republican presidential candidate said that, his political campaign skipped a beat. (Remember when Rick Perry said those who oppose in-state tuition for immigrants brought to this country illegally don’t “have a heart.” It didn't go over well.)
Bush is also supportive of Common Core, a series of nationalized education standards, that he says is necessary to ensure American children can compete with kids around the world. For conservatives – including the likes Louisiana Gov. Bobby Jindal who will likely run for president in 2016 – Common Core represents a classic case of the federal government thinking it knows best, as the Post said.
3) Dynasty
It's undeniable: While some have argued that Jeb Bush may be the best candidate among his family, and one of the best in his party, other pundits say that no amount of political detox could remove the toxicity of the Bush name.
While 73 percent of CEOs may favor a Bush candidacy, many Americans have indicated that they're ready for fresh candidates and names – even Jeb's own mother, Barbara Bush, who famously said last year that America "had enough Bushes." An NBC/Wall Street Journal poll indicates that two out of three Americans (69 percent) say they agree with Barbara Bush.
"America is supposed to be a democracy and, as such, its citizens should not tolerate aristocratic oligarchs lightly," wrote historian and columnist Timothy Stanley for CNN. "If Jeb Bush ran and won, there would have been no decade without a Bush in the White House since the 1970s. And no Republican ticket would have won without a Bush or a Nixon on it since 1928."
As Michael Brendan Dougherty wrote for The Week, for the Bushes, "third time's a harm."
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