WASHINGTON — Jeb Bush plans to address a crowd of skeptical conservatives in Washington this week, a challenge complicated by his more moderate views on immigration and education and on the historically awkward relationship between the Bush family and the GOP’s right wing.
The presumed front-runner in the early field of potential Republican presidential primary candidates is scheduled to speak Friday at the Conservative Political Action Conference, an annual event that will feature a lineup of national competitors jockeying for attention.
Bush’s appearance carries the most suspense. He will be wrestling with lingering conservative distrust from previous Bush presidencies while trying to paint a vision broad enough to straddle factions of the Republican Party — which is even more polarized than when his father and brother occupied the White House.
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Bush is planning to tout his conservative record during his eight years as Florida governor, according to those who have spoken to him recently, while not shying away from positions that give many conservatives pause: his moderate position on immigration and his advocacy of Common Core education standards.
“The governor is aware there are some conservatives who have questions about where he stands,” said Jim Towey, a longtime confidant of the Bush family. “The good thing for Jeb is he has a record. It’s easy to change words and make pronouncements and sound like a conservative. But governing like a conservative is a real challenge.”
Although no other family has so dominated Republican politics over the past quarter-century, the Bushes have not always enjoyed widespread support of conservatives. During the 1980 presidential primary campaign, George H.W. Bush derided Ronald Reagan’s proposals to cut taxes for the wealthy as “voodoo economics.” Later, after serving eight years as Reagan’s vice president, Bush pledged at the 1988 Republican National Convention: “Read my lips, no new taxes.” Two years later, he enraged conservatives when he agreed to raise taxes as part of a budget deal with Democrats.
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The elder Bush also had to fight back against the idea that he wasn’t tough enough — a notion that Newsweek memorably put on its cover in 1987 with the headline, “Fighting the Wimp Factor.”
When George W. Bush was laying the groundwork for his own presidential campaign, he was pilloried by conservatives who were gathering at CPAC in 1999. Senator Lamar Alexander said George W. Bush was using “weasel words,” while Steve Forbes warned the party not to be “seduced by the siren song of these mushy moderates.”
George W. Bush eventually won over many conservatives, partly through a focus on his born-again Christianity that helped him make inroads with the evangelical right. But Tea Party activists have grown upset about his government spending, and his willingness to bail out large financial institutions during the 2008 economic collapse.
While many view Jeb Bush as more conservative than his brother or his father, he still faces an uphill battle.
“Jeb Bush, I think, thinks it’s owed to him, it’s the Bush dynasty,” said Jane Aitken, the founder of the New Hampshire Tea Party Coalition. “But the grass roots is like, ‘Nooo.’ I don’t know of anybody who says, ‘Oh yeah, I’ll vote for Jeb Bush.’ ”
Bush and his allies argue that he governed conservatively in Florida from 1999 to 2007. They cite lowering taxes, fighting for school vouchers, and privatizing state jobs. But his last day in office was eight years ago, and fresher in the minds of many conservatives are his support of granting legal status to many illegal immigrants, and pushing for national education standards.
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“When Jeb left Tallahassee, he left as a conservative former governor,” said David Keene, who has led the American Conservative Union and the National Rifle Association and is now opinion editor at the Washington Times. “Now he’s the former conservative governor. And there’s a big difference.”
And just as Bush’s father was caricatured as a “wimp,” some conservatives worry that Jeb Bush doesn’t have the fire and passion it will take to go up against the presumed Democratic front-runner, Hillary Rodham Clinton, and her family’s brand of cut-throat politics.
“What he often does . . . is he comes to an event and lectures the Republican Party or lectures conservatives about their tone, about how they can attract different kinds of voters,” said Gary Bauer, a conservative activist and onetime presidential candidate who is president of American Values. “The grass roots wants evidence you are tough enough, direct enough, to confront what the left is doing.”
Bush so far has eschewed the harsh tone that often dominates today’s politics. Last week, for example, many conservatives cheered when Rudy Giuliani said President Obama does not love America, he “wasn’t brought up the way you were brought up and I was brought up.”
While other possible presidential contenders declined to repudiate the comment, Bush voiced his disapproval with the former mayor of New York. “Governor Bush doesn’t question President Obama’s motives. He does question President Obama’s disastrous policies,” Bush spokeswoman Kristy Campbell said in response.
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The problems that Bush faces with the conservative base are similar to the ones that Mitt Romney faced during the 2008 and 2012 Republican primary races.
Despite makeover efforts — including calling himself “severely conservative” at CPAC in 2012 — Romney had trouble attracting activists on the right, in large part because of his health care plan in Massachusetts.
CPAC is a three-day conservative gathering that has the feel of a trade show, carnival, and political convention all wrapped into one. It is one of the largest, most high-profile gatherings of conservatives, and it’s a key stopping point this year for presidential hopefuls.
On Thursday and Friday, many of the potential candidates will speak before the crowd. Bush is forgoing the typical speech and instead will participate in a 20-minute question and answer session that is being moderated by Fox News host Sean Hannity.
“It would be very easy for him not going to CPAC. Conventional wisdom says if you want to have a nice day, don’t go to CPAC,” said Chip Felkel, a veteran South Carolina political consultant who is unaffiliated with any of the candidates.
“But it’s good for him to go. He needs to go. That’s a constituency people don’t expect him to spend a lot of time with,” Felkel said. “He’s willing to go and have a conversation with people. He’s not going to run away from people he disagrees with.”
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The calculation for Bush also seems to be that it’s better to address than ignore a skeptical constituency. And while he has skipped other gatherings of conservatives, Bush is planning to travel next week to Iowa, his first trip to court caucus-goers in a state where conservatives have great sway.
“I think they’re putting together an impressive campaign. They’ve got a lot of familiar faces and names,” said Craig Robinson, a former political director of the Iowa Republican Party who now runs the influential website the Iowa Republican. “But I feel like they’re a little behind the 8 ball. They’ve got a lot of work to do here.”
Matt Viser can be reached at matt.viser@globe.com.