Jeb Bush will have to overcome a number of hurdles in order to secure the Republican Party’s nomination for president in 2016. The most significant of these seems today to be the conservative base’s antipathy towards Bush’s positions on a variety of critical policy matters. But the former Florida governor clearly not concerned about the conservative base. He is, however, deeply concerned about winning the support of the Republican donor class and the press.

On Wednesday, the media cooed over the political savvy evidenced by Jeb Bush’s decision to release 10 years of personal tax filings. That the political press was moved to swoon over a Bush of any variety is in itself a feat, but it was the implicit effort to distance himself from Mitt Romney that won the admiration of the Beltway media.

Via Ben White at Politico:

The effort is meant in large part to eliminate comparisons to 2012 Republican nominee Mitt Romney, who waited until September of 2012 to release just two years of tax returns after months of pressure from Democrats and even members of his own party to be more open about his extensive wealth.

As Romney held off on the tax return release, Democrats successfully painted him as an out-of-touch multi-millionaire who had something to hide. The nascent Bush campaign – which is already attempting to craft a message to appeal to middle and working class Americans – plans to move early on to crush efforts by either Democrats or rival Republicans to paint the former governor as a super-wealthy creature of Wall Street.

Some clever political analysts like RedState’s Dan McLaughlin observed that this move is, in large part, aimed at the skittish GOP donor class. There is evidence to support that conclusion in White’s story which goes on to suggest that the political press will never absolve Bush of his aristocratic background in the same way that they never forgave Romney for his accidents of birth or private sector acumen.

“This week also displays Bush’s challenge in pushing back against efforts to portray him as a wealthy member of a political dynasty with patrician, Wall Street roots,” White reported. “Bush is scheduled to be in Greenwich, Conn. on Wednesday, home to some of the wealthiest financial elite, for a fundraiser for his newly created PAC. Greenwich was home to Bush family patriarch and former Senator Prescott Bush.”

The panicky GOP donor set is going to need all the wooing they can draw out of Bush; convincing the Republican moneyed class to financially back another member of this dynastic political family while “Bush fatigue” is a living memory is going to be an uphill battle. But to suggest that Bush’s campaign has thus far been directed squarely at the donor set misses half the picture. He is also speaking directly to the press.

How else do you explain Bush’s insistence that congressional Republicans should do away with votes to repeal the loathed Affordable Care Act? “We don’t have to make a point anymore as Republicans,” Bush said, noting instead that the Republicans should focus on putting forward Obamacare alternatives (there are already several). Republican donors and the conservative grassroots are equally opposed to the Affordable Care Act. Only the press has bought into the notion that the ACA is settled law and the GOP’s votes repeal this persistently unpopular and unworkable law are tantamount to admissions of incompetence.

How else do you explain Bush’s inexplicable and tedious swipe at the Republican base before an audience of CEOs at an annual Wall Street Journal event in which he asserted that the eventual GOP nominee must “lose the primary to win the general without violating your principles.” While this comment requires a lot of translating, it is hard to miss the gratuitous insult directed at the majority of Republican voters who are deeply mistrustful of Bush’s position on issues like immigration and Common Core.

Much of the donor class may be foursquare behind comprehensive immigration reform, but they are as mistrustful of the Common Core curriculum as are many Republican and independent rank and file. This convoluted, top-down education reform has only one constituency: Democrats and their supporters in the media.

According to some, much of the frustration over Common Core is based on hostility towards the Obama administration (a sentiment shared by Democratic strategist Ed Kilgore). A recent report in The Miami Herald attempted to suggest that even the center-right wing of the GOP has come to terms with Common Core, and it is only a matter of time before the party gives up the ghost of opposition to this program.

There are conservatives who support the standards, including members of big business groups like the U.S. Chamber of Commerce and some right-of-center education think tanks.

Sol Stern, a senior fellow with the right-leaning Manhattan Institute for Policy Research who favors the Common Core, said Bush stands to gain some points for “looking courageous and standing up to some very silly arguments.”

“All this stuff about Obamacare and the feds are dictating this? It’s total nonsense,” Stern said. “If Bush goes out on the stump and debates [on this topic], he can make very strong points.”

But even The Herald conceded that, according to a recent PDK/Gallup survey, 60 percent of all Americans (not merely voters) and over three-quarters of self-described Republicans are opposed to the Common Core standards.

If Bush’s presidential campaign is aimed at appealing to a constituency in the press, it is a strategically sound approach (if a bit distasteful). Jeb Bush probably remembers how his father and brother’s legacies were largely undone by unfair coverage of Hurricane Katrina, the 1991 recession, electronic cash registers, and golf outings. A friendly press can be a powerful ally, but the media will not send a single delegate to Cleveland in 2016.

Jeb Bush needs to stop alienating the party’s base under the offensive assumption that they can always be tended to later, when there is time. The time is now. If he is serious about leading the GOP, Bush must also like the GOP. At least, he should demonstrate that he can convincingly pretend that he does.