The pragmatists were dismayed by Bush's recent struggles to explain what he would have done differently than his brother in Iraq. That ordeal left Republicans fearing that if the party nominates Bush, Democrats would find it too easy to convert the campaign into a referendum on returning to the policies of the last Bush administration.
Bush's problems with the Right are rooted in two other elements of his brother's legacy. Though staunchly conservative on most issues, George W. Bush backed a pathway to citizenship for undocumented immigrants and an aggressive role for Washington in education reform. Politically, each idea was intended to court voters beyond the GOP base.
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Conservatives chafed against those policies during George W. Bush's presidency and, after he left office, successfully eroded support in the party for both ideas. Jeb Bush, though, threatens that victory. The younger Bush has said he would accept either a pathway to citizenship or permanent legal status for the undocumented, and he has defended the Common Core curriculum reform (while rejecting President Obama's effort to advance it through federal policy).
Can Bush win these arguments in the GOP? Despite loud resistance from prominent conservatives, "Jeb Bush's view on immigration is "¦ more acceptable to Republican primary voters than most people assume," notes Peter Wehner, senior fellow at the Ethics and Public Policy Center. While many Republican voters view immigration skeptically, in the latest Pew Research Center survey, nearly three-fifths of the party (including GOP-leaning independents) said the undocumented should be allowed to remain legally inside the country. That number reached nearly two-thirds among the college-educated Republicans who are Bush's natural constituency.
Bush's continued support for Common Core may be a tougher sell with Republican voters. But it's probably less important for Bush to win the specific debates over immigration and education than to subsume both issues beneath bold new domestic and foreign policy ideas that excite GOP voters. So far he hasn't done that. Unless Bush can shift his campaign's focus toward the country's future, he's likely to remain stuck in debates over his party's past. And driving in reverse is no way to win a race.
(RELATED: Jeb Bush to National Review: 'I Love You,' But 'You're Wrong on Immigration.')
Hillary Clinton, who kicks her campaign into higher gear with a major address on Saturday, hasn't faced nearly as much pressure yet within her party but could eventually confront her own legacy trap. Her announced rivals, Sen. Bernie Sanders of Vermont and former Maryland Gov. Martin O'Malley, have denounced free-trade and financial-deregulation policies that Bill Clinton pursued. Other Democrats worry about the Clinton family heritage of ethical controversy. On both fronts, Hillary Clinton's challenge will be less to defend that record than to transcend it.