"I know — I kinda know — how a Republican can win," Jeb Bush said last December.

Speaking to a group of businessmen in Washington, DC, the former Florida governor made his pitch. "It has to be much more uplifting, much more positive, much more willing to be practical," he said. A successful candidate, he continued, would be willing to "lose the primary to win the general, without violating your principles."

That line was widely interpreted as Bush's declaration of war against the GOP base, and he's made many similar remarks. A year ago, he called unauthorized immigration an "act of love." Not long before that, he argued that "way too many people believe Republicans are anti-immigrant, anti-woman, anti-science, anti-gay, anti-worker." And in February, he called the opportunity gap "the defining issue of our time."

But all of these remarks have something in common: their moderation is rhetorical, not substantive.

There's a great deal for conservatives to love in Bush's Florida record

When it comes to actual policy positions — those he advocates for now, and those he fought for and implemented in Florida — Bush has surprisingly few dramatic differences from staunch conservatives. His biggest heresy is his continued support for a path to legal status for unauthorized immigrants. And some education reform policies he's backed, like the Common Core, have also become controversial on the right.

After that, though, there's little for conservatives to complain about in Bush's record, and a great deal for them to love. As governor, he slashed taxes, rolled back regulations, and privatized government functions. He lifted restrictions on guns, and fought hard for both pro-life causes and school vouchers. Joshua Karp, communications director of the Florida Democratic Party, told me that Bush "did a lot more damage" to the state than its current governor, Rick Scott — because "he was more effective."

Indeed, Bush's adoption of warm and fuzzy rhetoric is a deliberate strategy — one designed to make electoral victory easier, so he can better implement conservative policies afterward. And it's an approach deeply rooted in his experiences in Florida, where Bush lost his first run for office because he was viewed as a far-right bomb-thrower. It was only after he learned to present a more moderate image that he won, and gained the power to turn his actual conservative ideas into reality.

So Bush isn't trying to break with conservatism. He's trying to save it, by using more appealing rhetoric to sell it to the public so a Republican can win the presidency.

The big question is whether GOP voters will want him to do so — or whether his own last name makes his pitch a lost cause.

"The Ted Cruz of gubernatorial candidates"

On July 27, 1994, Jeb Bush learned how badly a Republican candidate could be burned by being perceived as too extreme.

The 41-year-old first-time candidate for governor was attending a televised town meeting in Tampa, alongside his four rivals for the nomination, when attendee Angelica Gonzalez asked a question. "I'm a Latina, a woman of color, and on top of that I'm black," she said. "What are you doing for the African-American community? Tell me. Issues."

When one of Bush's opponents answered by bringing up welfare, Gonzalez was unsatisfied and repeated her question. So Bush gave his own response — one that turned out to be ill-advised. "It's time to strive for a society where there's equality of opportunity, not equality of results," he said. "So I'm going to answer your question by saying: probably nothing."

The audience gasped, according to a recounting in the St. Petersburg Times. "At least I know I'm not going to vote for him," Gonzalez told the paper afterward. "At least he's honest."

"His mind ran faster than his filter," says Mac Stipanovich, a top aide to Bush during that first campaign. "What he meant there was a perfectly defensible position. But the way he said it, and the way it could be so easily taken out of context and misinterpreted, was a function of inexperience."

Bush called himself a "head-banging conservative"

This particular remark was especially blunt, but it did characterize Bush's general approach in that campaign — he was a hard-line conservative who didn't sugarcoat anything. "I don't cloak my language to try to be all things to all people," Bush told the New York Times that year. "Arguably, he was the Ted Cruz of gubernatorial candidates," says Matthew Corrigan, author of the book Conservative Hurricane: How Jeb Bush Remade Florida and a political scientist at the University of North Florida.

Bush called himself a "head-banging conservative," talked about "blowing up" state agencies, and said he wanted to "club this government into submission." He bragged that he would sign many more death warrants as governor, and proposed that the names of juvenile delinquents should be publicized so people would "know who the thugs are in their neighborhoods." He chose state Rep. Tom Feeney, the Christian Coalition's legislator of the year, as his running mate, despite Feeney's history of extreme views.

The common perception was that Bush was running on this agenda because he truly believed it. "Jeb has strong opinions," says Paula Dockery, a former Republican state senator in Florida, who was friendly with Bush during that early campaign. "Some might call him stubborn. Here he is running for the first time, and he believes you have to stand strong for the principles that you believe in."

There was a political rationale, too. Jeb's father had recently failed to win a second presidential term, after he infuriated conservatives by signing on to a deficit reduction deal that raised taxes. During Jeb's own campaign, he called his father's deal "a huge strategic error" that "left so many people unmotivated to work for his reelection." He had, he said, "learned the lesson." His hard-line rhetoric and policy proposals let him outflank his rivals in the primary, and he topped the second-place vote-getter in the five-person race by 28 percentage points.

But when Bush was pitted against the incumbent governor, Lawton Chiles, his strategy backfired. Chiles, a wily Democrat who had served three terms in the Senate and was something of a legend in the state, seemed to have the corners of his lips permanently pulled back in a grin — and for good reason.

Chiles's approval ratings had looked quite bad when Bush first launched his run, but as the two went head to head, Chiles bounced back. He contrasted his own deep Florida roots with Bush's relatively recent arrival in the state, never missing an opportunity to throw out a homey aphorism. But he also portrayed Bush as a right-wing extremist. "I love the state of Florida," Chiles said during a debate held at Walt Disney World. "It is not a toy. It is not a place to allow somebody to experiment." "Lawton Chiles did an excellent job down the stretch in reminding moderate and rural voters that he was one of them, while Jeb was identified with hardcore ideologues," says Keith Fitzgerald, a former Democratic state legislator and political scientist.

Just days before the election, with the polls extremely tight, Chiles's team played one last card. The campaign authorized secretive phone calls under the names of phony groups to at least 70,000 senior citizens in the state. "We're calling to let you know that Jeb Bush is no friend to seniors," one script read. "Jeb Bush's running mate wants to abolish Social Security and calls Medicare a welfare program that should be cut. We just can't trust Jeb Bush and Tom Feeney." The charges were exaggerated, but months of right-wing rhetoric from Bush had made them sound believable.

The 1994 elections proved to be a historic Republican landslide. The party's candidates took control of both chambers of Congress — the House of Representatives for the first time in 40 years — and netted 10 new governor's seats and control of many more state legislators. Even Jeb's older brother George W. Bush unexpectedly managed to defeat Texas's well-liked Democratic governor, Ann Richards.

Jeb was practically the only Republican in a competitive contest to lose. His race was close — he lost by 1.5 percentage points, or a margin of just 64,000 votes — but that was little comfort. The day after the election, he sounded despondent. "It's over. I lost, and I'll go on to the next part of my life," he told the Associated Press. "Whatever lessons there are will become clear over time. I thought we were going to win."

He won the primary, but he lost the general.

"I have been changed in the last four years"

"Conservatives have failed to learn the language, failed to understand African-American concerns and failed to reach out and care," read a damning 1995 report on the GOP's prospects in Florida. "Just as alcoholics must first admit they have a problem before they can begin to deal with it, so too must conservatives admit that the old ways will ensure the same dismal results."

The report was published by Jeb Bush's new think tank.

The once and future candidate had wasted little time in trying to figure out where he'd gone wrong, so he could position himself for another try for the governorship. His new Foundation for Florida's Future hired several of his top campaign aides, and conducted polling and held focus groups into what the state's voters wanted.

Bush soon concluded that his main problem was that his rhetoric lacked compassion. "The big lesson of '94," he recently told the Weekly Standard's Andrew Ferguson, was that "the thing I didn't do was show my heart. I didn't show who I was." He continued: "In politics, you put a human context around things, and you show your heart."

So over the ensuing four years, Bush gave himself a political makeover. Stylistically, the man who ran for governor in 1998 would be nearly unrecognizable next to the old "head-banging conservative."

Bush hit upon education policy as a promising area where conservative, market-oriented principles could be melded to a compassionate message. Where in his first campaign, he had framed his arguments around getting rid of government, he now emphasized increasing achievement and solutions.

And he built bridges. T. Willard Fair, the head of the Urban League of Greater Miami, had never spoken to Bush before he got a call one day in 1995 saying the former candidate wanted to donate some money to one of Fair's groups. Fair expected he'd get a photo op out of it, and that would be the end of that. Instead, Bush struck up a conversation with Fair, and the two men started to bond, discussing their families as well as well the achievement gap.

"I found out we shared the same concerns," Fair says. "And he said, 'Why don't you start a charter school?' I said, ''What is a charter school?'"

The debate over charter schools, which are funded by taxpayer money but operated by independent groups, was relatively new — the first one in the country had just been opened in St. Paul, Minnesota in 1992. But charters seemed to Bush to present a constructive alternative to the problem of failing inner-city schools, particularly because they had to follow fewer regulations and didn't have to employ unionized teachers.

The problem was that Florida law didn't yet allow for charter schools to get state funding — but the legislature was then debating a bill to change that. "I decided to work with him to get the law passed, and we crisscrossed the state," Fair says. Their efforts were successful — the bill became law in 1996, and Fair and Bush co-founded the Liberty City Charter School soon afterward. (The school has since closed down, but Fair remains an enthusiastic supporter of Bush today.)

More work needed to be done on Bush's image. As the campaign drew nearer, he went on what he called a "listening and learning" tour. He visited domestic violence shelters, hospitals, and family court sessions. And he began referring to himself as a "compassionate conservative." (There were personal changes as well — he converted to Catholicism, his wife Columba's faith, around this time.)

Opportunity was Bush's new watchword. "We are creating two Floridas, a version of apartheid if you will, where people who don't even have the ability to grab the first rung of the ladder of opportunity are being left behind and others have a chance to pursue their dreams," he said in a Tampa speech reminiscent of his current "Right to Rise" rhetoric.

By the time Bush officially announced his second campaign for governor, he wanted to be sure people had noticed his new approach. "In the last three months, I've campaigned more in the African-American community than any Republican probably since Reconstruction," he told reporters. "I have been changed in the last four years," he told a group of Jewish Democrats.

It was surely true that Bush has changed — but how much? "The principal difference between Jeb Bush in ’94 and Jeb Bush in ’98 had nothing to do with his principles or his character, but was about his presentation," says Stipanovich, the former Bush campaign aide. "He learned that you need to be near the center to win the general election — if not in your heart, then in your rhetoric."

"He didn't change his policies. He changed how he described them." "In ’94, let’s say Jeb believed 10 things, all of which would’ve been a conservative position at the time, very strongly," Stipanovich continues. "He would talk about all 10 of them, even if the people he was speaking to only agreed with him on four. In ’98 he believed the same thing about those 10 issues — but he had learned to just talk about the four."

Most of all, it was the hot-button social and racial issues that he now handled more deftly. Bush hardly mentioned his enthusiastic backing of the death penalty, a fixture of his first campaign. He downplayed abortion and welfare, and while he maintained his support of school vouchers, he argued that they were only a minor part of a broader plan that would fix public schools statewide. Dockery, the former state senator, says, "He softened his approach, but he didn't change his policies. He changed how he described them."

The new strategy was successful. Bush ran unopposed in the primary, and once the general rolled around, he again defied the national trend. While the national GOP was damaged by the effort to impeach President Clinton, and performed worse than expected, Bush won a comfortable, double-digit victory. "This is a victory of inclusion rather than exclusion, of offering hope rather than dividing," Bush said at his victory rally.

"The ideology that I believe"

Reflecting on his first two campaigns to the Weekly Standard this year, Bush said, "I learned a lot. And the tone of my language is reflected in what I learned." Yet he made sure to point out: "The ideology that I believe, the belief in limited government — that didn’t change."

Once Bush took office in Florida, he had the chance to put his ideology into practice — and by virtually all accounts, he did a very effective job of it. "Florida was one of the most progressive states in the South by far," says Keith Fitzgerald, the political scientist and former Democratic legislator. "And Jeb just picked it up and moved it."

The centerpiece of his agenda, and his legacy, was education. Conservative intellectuals like Milton Friedman and Terry Moe had long dreamed of applying market forces like choice and accountability to government-run public school systems. Bush was among the first to move their ideas from think tanks to the real world. Once inaugurated in 1999, he acted quickly to begin what was then "the largest experiment in public school education in the nation’s history," Matthew Corrigan writes in Conservative Hurricane.

Bush instituted yearly testing across the state — with teeth. He held back third-graders if they didn't pass reading tests or demonstrate reading ability. Schools themselves would be graded based on their students' test results; if the scores were bad, students would get the opportunity to transfer elsewhere. Some would be able to qualify for vouchers to pay for private school tuition, including at religious schools, in the country's first-ever statewide voucher program. Bush also signed new legislation that led to an even bigger boom in charter schools.

It was a massive overhaul, and one hotly opposed by teachers unions. But Bush sped it all through the state legislature so easily that Democrats soon dubbed him "King Jeb." The voucher program would eventually be struck down by state courts in a bitter defeat for Bush, but the bulk of his education agenda survived, and he's touting it this year. "Accountability for teachers and school administrators, assessment of student learning, high standards, and choices — these key elements of school reform work and we have the results to prove it," he said in a February speech.

On cutting taxes, Bush said, "I like it when people get mad that I do it"

The Republican-controlled legislature happily signed on to Bush's education agenda — and then Bush just as happily killed their pet spending projects. High-speed rail, river cleanup, and local arts centers were all deemed "turkeys" by Bush, who had a line-item veto. He vetoed $2 billion in legislative spending over his two terms, according to the St. Petersburg Times — and it was the GOP state House speaker, John Thrasher, who dubbed Bush "Veto Corleone." Bush also privatized as many government services as he could — everywhere from education to prisons to foster care to waste management, he looked for areas where work could be taken out of the government's hands.

Like his brother, Jeb Bush enthusiastically slashed taxes, to the tune of $13 billion or so over his eight years. His biggest overall cut was to a tax on stock and bond wealth loathed by investors. Bush went after it with particular vigor, calling it "insidious," and won its permanent repeal in 2006. "I will be the first governor to have cut taxes every year," Bush said. "I love it. I just think it's fantastic, and I like it when people get mad that I do it." Anti-tax activist Grover Norquist said at the time that Bush "should change his name and run for president."

Meanwhile, Bush became such a champion of right-to-life and anti-abortion causes that by 2005 he was calling himself "probably the most pro-life governor of modern times" in Florida. This was less because of new laws — the most sweeping abortion-related bills he signed were struck down by the courts — and more because of his unusual willingness to intervene in individual cases and controversies. "Bush believed in strong government intervention to support pro-life causes, and if that meant intervening in someone’s private life, he would do it," Corrigan writes. In two high-profile and tense abortion cases, Bush asked a state court to appoint a legal guardian for the fetus of a mentally disabled woman who had been raped, and tried to block a 13-year-old girl in state custody from getting an abortion.

But Bush's actions during the Terri Schiavo controversy became most famous of all. Schiavo had been in a persistent vegetative state for nearly a decade when Bush took office, but she hadn't left a living will. Her husband petitioned to have her feeding tube removed, but her parents objected, and pro-life activists began campaigning to keep Schiavo alive. When the courts sided with Schiavo's husband, Bush stepped in — he got Florida's legislature to pass "Terri's Law," which specifically gave him the power to reinsert her feeding tube.

Bush fought various court orders calling for the removal of Schiavo's feeding tube for a year and a half, but was unsuccessful in the end. The courts struck down Terri's Law, Schiavo's parents eventually ran out of appeals, and she died in 2005. Earlier this year, Schiavo's husband told reporter Michael Kruse that Bush put him through "a living hell." But this February, Bush maintained he had no regrets about the case, saying, "I acted on my core belief that the most vulnerable in our society should be in the front of the line. They should receive our love and protection."

When it came to gun policy, Bush similarly championed the causes of Second Amendment enthusiasts, working to pass item after item on the National Rifle Association's wish list. Foremost among these was the nation's first Stand Your Ground law, allowing people to use deadly force if they felt threatened in a public place, which Bush signed in 2005. Critics at the time dubbed it the "Shoot the Avon Lady" law, and it became the subject of national controversy after the fatal shooting of Florida teenager Trayvon Martin in 2012. But Bush still supports the law today. "In Florida, we protected people's rights to protect themselves," he told an NRA meeting in April.

There were some fights that Bush would have preferred to avoid. During his first year in office, activist Ward Connerly started gathering signatures to try to put a measure banning race-based affirmative action up for a statewide vote in 2000. Though Bush had long opposed racial preferences, he had just worked hard to improve his standing in Florida's African-American community, and a similar measure had recently caused intense racial controversy in California. Bush wanted to avert such turmoil — not least because it could have stoked black voter turnout in Florida that year and hurt his brother's presidential campaign.

"I have listened, and I have learned"

So "Jeb cut that Gordian knot with an executive order — and in a very conservative way," says Stipanovich, the former Bush campaign aide. In November, Bush announced he would use his authority to end all race-based affirmative action for Florida's public universities and state contracting, as part of his new "One Florida" plan. Instead, he argued, he'd better ensure diversity by guaranteeing that the top 20 percent of every high school graduating class would be admitted to state universities. He said his new policy "transcends traditional notions of affirmative action," rather than ending them.

Black leaders in the state weren't convinced, and they were outraged at what they said was a lack of consultation before Bush announced his plan. Two state legislators staged a sit-in in Bush's office complex, and protesters ended up marching on Tallahassee. All this led Bush to modify the plan a bit — "I have listened, and I have learned," he eventually said — but the bulk of it was implemented. The controversy petered out, Connerly ended up abandoning his ballot effort, George W. Bush was declared the winner in Florida by 537 votes, and Jeb now names the affirmative action overhaul as one of his biggest achievements.

Bush accomplished all this in a state that was closely divided between Republicans and Democrats — and, what's more, he did it with such political savvy that he won reelection easily, and was still popular when he left office. As a result, many Floridians from both parties find it bizarre that some conservatives outside the state view him as a RINO. "I'm kinda struggling with the belief that Jeb Bush isn't conservative," says Dockery. "While Jeb was governor, he was extremely conservative. He was a fiscal conservative. He was a social conservative. And to this day he remains exactly as he was when he governed the state of Florida."

"They want a viable candidate"

Once you understand Bush's background, and how well the pairing of moderate rhetoric with conservative policies worked for him in Florida, his decision to use the same playbook for his national run makes perfect sense.

So when Bush signaled his entrance into the race last December, the business establishment of the GOP was thrilled. There was a common perception among party elites that Mitt Romney's 2012 campaign went awry in a few related ways. He was pulled too far to the right during the primary, he made various rhetorical gaffes such as his "47 percent" comment that suggested he was uncaring, and he failed to appeal to Hispanic voters (instead suggesting that his policies would make unauthorized immigrants "self-deport").

Bush, in positioning himself for a run, promised he'd make up for all three of these shortcomings, while sticking to conservative principles. His bold-sounding declaration that a candidate should "lose the primary to win the general" signaled that he wouldn't pander to the base. Repeated statements akin to what he said in February — "I have to show that I care about people, about their future" — showed off his more compassionate rhetoric. And he seemed to have a shot at winning much more of the Hispanic vote, due to his unapologetic support for a path to legal status for unauthorized immigrants, not to mention his Mexican-born wife and fluency in Spanish.

"You look at his record in Florida. He’s a conservative! But he’s a constructive conservative. He’s also a happy conservative," says lobbyist and Bush supporter Dirk Van Dongen. "The challenge for Democrats with Jeb is that he talks like a moderate," says Joshua Karp, the Florida Democratic Party staffer.

But so far, Bush's effort has been much less successful than he initially expected. Despite reportedly raising boatloads of cash, Bush hasn't broken away from the rest of the enormous GOP field in polls, either nationally or in early states. Future nominees have been in worse shape at this point, but it hasn't been an inspiring beginning. He'll try to start turning all this around when he officially announces his campaign Monday.

Bush now needs to convince blue-state Republicans that his last name won't hold him back Bush's difficulty winning over conservatives has often been touted as an explanation for his troubles. The party has indeed moved right since he left office eight years ago — but on most substantive issues, Bush still fits in it quite well. Even his past support for the Common Core, which is unpopular on the right, seems unlikely to hurt him very much, particularly because he's already made it clear that it will play no part in his campaign. "The federal government has no role in the creation of standards, either directly or indirectly," Bush said in February. "The role of the federal government, if there's any, is to provide incentives for more school choice."

In supporting a path to legal status for unauthorized immigrants, though, Bush is genuinely out of step with his party's base. It's the one matter of substance that he does want his party to moderate on, and he's unapologetic about it. "The simple fact is, there is no plan to deport 11 million people," he told the Conservative Political Action Conference this year. "We should give them a path to legal status where they work, where they don't receive government benefits, where they don't break the law, where they learn English, and where they make a contribution to our society." Though Bush is the most outspoken in the GOP field on this, he's far from alone in believing it. Most of his main rivals have at some point voiced support for similar policies, with even Ted Cruz saying he'd theoretically be open to such a proposal.

Overall, though, the skepticism the most conservative GOP voters feel about Bush won't doom his campaign — because he was never going to win them anyway. Instead, Bush's most likely path to the nomination always counted on blue-state Republicans, who are more important in determining the party's nominee than many think, as the Upshot's Nate Cohn wrote in January. "Part of why McCain and Romney got the nomination is they appealed to business-class Republicans outside the South, people who are conservative but pragmatic as well. They want a viable candidate," Boston College political scientist Dave Hopkins told me last year.

These are the voters Jeb needs, and he's conservative enough that they won't worry too much about his purity. Instead, they'll be concerned about his electability — because of his last name. And, worryingly for him, if those Republicans want a nominee who will use appealing rhetoric to sell conservative principles, and who might win Hispanic voters, they have another option.

Sen. Marco Rubio's entrance into the race in April was a serious blow to Bush's hopes — not just because he's also from Florida, but because the approaches the two men take to politics really are quite similar. Unlike bomb-throwers on the right, Rubio consistently frames his quite conservative views in inspiring and appealing terms. Indeed, he's a much better speaker than Bush. And his fresh face and name seem to present a better contrast to Hillary Clinton.

Bush has presented a compelling political strategy for how he wants to lead the Republican Party and get conservative policies enacted into law. It's a strategy that worked for him in Florida, where he remade himself and transformed the state. But it will be far harder to execute at the national level, given his own last name, and his close identification with one of the most polarizing and controversial presidents in recent decades. If the Bush name looks like it will be a millstone in the general election, Republicans searching for a viable candidate may look elsewhere.

"Yesterday is over," Rubio likes to say. When it comes to George W. Bush's presidency, Jeb had better hope voters agree — or else he might lose that primary after all.