Will Jeb stumble in Iowa?
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With no love lost for Jeb Bush among the Republican base, the Iowa caucuses could be an early stumbling block in his 2016 quest. 

The former Florida governor’s business-friendly stances and willingness to criticize GOP hard-liners make him popular with the donor class. But the first-in-the-nation state hasn’t been kind to establishment candidates in recent years. 

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And just after he announced this week he’s “actively exploring” a presidential bid, some Iowa activists are already torching Bush’s credentials. 

“He's on the wrong side of every issue that matters most to conservatives right now,” said Steve Deace, an influential Des Moines-based conservative radio host.

Deace ripped Bush for his support for immigration reform and Common Core education standards, apostasies to the conservative cause, before saying he’d “bet my mortgage” against Bush performing well in Iowa.

“He's not just for amnesty, he's an apostle for it. He's a pitchman for Common Core, and there's more organized conservative opposition to Common Core on the ground than anything besides ObamaCare,” he said. “He offers nothing, truly nothing. I don't know why any who's even a modicum of a conservative would vote for him.” 

The Iowa GOP caucuses have punished establishment candidates in recent years. 

The process is often dominated by the state’s large population of religious conservatives, and a pair of cash-poor candidates defeated better organized and much better funded foes by tapping into voters’ frustration with the GOP elites the last two presidential races. 

Former Arkansas Gov. Mike Huckabee (R) pulled off a come-from-behind win over former Massachusetts Gov. Mitt Romney (R) in 2008, while former Sen. Rick Santorum (R-Pa.) edged Romney in 2012.

Iowa Republicans from across the party believe Bush may have a chance in the state if he dedicates the time and energy to woo voters. But, they say, he has a ton of work to do to convince Iowa conservatives that he’s one of them.

“His hurdles are going to be high,” said Bob Vander Plaats, an Iowa social conservative leader and former gubernatorial candidate.

Vander Plaats warned of “Bush fatigue” and said his immigration position “looks a lot like amnesty, not compassionate conservatism.”

The onetime Huckabee backer said Bush’s biggest problem was his education position.

“There are a lot of people that believe our schools have been hijacked by the federal government and they've lost local control. I just don't see anybody getting the nomination who advocates for Common Core,” said Vander Plaats. 

It’s not impossible to win Iowa as the establishment favorite, even for those with some major policy disagreements with the base. Jeb’s brother George W. Bush proved that in 2000, and their father, George H.W. Bush, did when he defeated Ronald Reagan in Iowa in 1980.

Sen.-elect Joni Ernst (R-Iowa) pulled off a dominant primary win earlier this year by wooing both hardline conservatives and establishment figures. And Iowa Gov. Terry Branstad (R) successfully led a recapture of the state GOP from the control of religious and libertarian activists last year, intent on making sure Iowa’s caucuses would be an amenable place for Republicans of all stripes.

Some say Bush’s conservative record as governor gives him a platform, while others point out that he’ll likely have the money to build a top-notch organization — and can draw on a crop of GOP organizers who cut their teeth working for his brother.

“There's a large contingent [of voters] that could support Jeb Bush while everyone else tries to outflank each other on the right,” said Iowa GOP strategist Tim Albrecht, Branstad’s former spokesman. “It's important for him to highlight what he was able to do as governor and what the actual results are.”

Republican candidates also haven’t had to win Iowa to win the nomination in recent years — neither Romney nor John McCain did, though both placed strongly in the state. But it's rare for a candidate to compete and fail badly in Iowa and still win the nomination. 

Iowa strategists say to succeed, candidates don’t have to shed their so-called “establishment” appeal — but they do have to prove that they’re still strong conservatives and earn voters’ trust by traveling the state heavily. 

Ultimately, Bush will need to talk a lot more about his record as governor and figure out how to better finesse disagreements with the base if he wants to succeed.

“I see no reason why Gov. Jeb Bush won't be very competitive, just as his brother was in 1999 and 2000,” said Dee Stewart, who was the Republican Party’s executive director during those caucuses. “He has an impressive record, he's regarded by those he worked with and for whom he governed as a solid conservative.” 

Bush’s brother had strong ties with the state’s large evangelical Christian population as well as with more business-focused Republicans. Ernst had the quiet backing of Branstad and many in the state’s GOP establishment, but was also a proven conservative activist who left almost no room to be outflanked on her right. Her rise came at the expense of more moderate businessman Mark Jacobs, who collapsed in the primary despite spending millions. 

“Any candidate that's perceived as being establishment has to get in the trenches with Iowa conservatives and prove they have the credentials to be their favorite in the caucuses,” said GOP Iowa state Sen. David Johnson, a veteran of Iowa campaigns and a 2012 backer of Texas Gov. Rick Perry. 

It’s an open question whether Bush, who has regularly criticized conservatives in his party over the years, is ready to play nice and woo base voters. He’s continued to emphasize immigration and education, his two biggest problem areas, in recent interviews rather than focusing on his time as a conservative executive. 

Also, his recent comments that GOP candidates should be willing to "lose the primary to win the general without violating your principles” indicate he’s happy to remain combative with the more conservative corners of his party.

Many in the state are skeptical whether Bush is ready for a crowded Republican field of candidates — including others competing for the “establishment” mantle, like New Jersey Gov. Chris Christie, Florida Sen. Marco Rubio, Louisiana Gov. Bobby Jindal, Texas Gov. Rick Perry, Wisconsin Gov. Scott Walker and others who may be able to appeal to center-right voters.

And that includes some who view the Bush family fondly.

“It's not going to happen for Jeb Bush here,” said one Iowa Republican official who’d been involved in helping his brother win the 2000 caucuses. “I just don't see him campaigning here and succeeding.”