Jeb Bush. Not conservative enough. Try as I might, it remains impossible to see these two concepts as even remotely related. John Ellis Bush, the second son of George Herbert Walker Bush and Barbara Bush, who during his first run for Florida governor in 1994 cheerfully called himself a head-banging conservative, a hang-’em-by-the-neck conservative … who during his second run for Florida governor in 1998 had to craft for himself a more compassionate persona so as not to scare off independent voters … that Jeb Bush has come to be viewed with suspicion by the uber-conservative, Tea Party wing of his Republican Party?

Admittedly, there are his heresies on Common Core and immigration, the two hottest-button issues of the day in that world—but that’s enough to make Jeb a moderate? Really?

For those of us who covered Jeb’s two terms in Tallahassee, this is beyond mind-boggling. On issue after issue, Jeb’s track record in Florida pushed conservatism’s envelope to the breaking point.

For anti-tax conservatives, Jeb slashed the state’s collections by a cumulative $14 billion over his eight years. For the devoted subset of supply-siders: The bulk of these cuts came via the complete repeal of Florida’s decades-old wealth tax on financial instruments. It pretty much had been the only progressive tax the state had, since Florida’s constitution forbids an income tax.

For anti-spending conservatives, Jeb line-item vetoed hundreds of millions of dollars in hometown projects from the state budget year after year.

For small-government conservatives, Jeb eliminated thousands of jobs by outsourcing huge swaths of state duties, including the massive human resources function and the state purchasing office.

For law-and-order conservatives, Jeb championed tough-on-crime bills like “10-20-life” for gun offenders and three-strikes legislation for repeat offenders. He jammed through the legislature a death-penalty overhaul drastically limiting appeals for condemned inmates (it was soon afterward struck down, however, by the Florida Supreme Court).

For pro-gun conservatives, Jeb approved an enhanced concealed carry law and, infamously, the NRA-written “Stand Your Ground” law. (After Trayvon Martin, Jeb said he did not believe it should have been applied in that instance.)

For religious conservatives, Jeb rammed through education bills that created the first statewide school voucher programs in the nation, and then spent years defending them against oversight attempts. He approved the “Choose Life” license plate and sent state money to groups that counseled women against having abortions. And, famously, he pushed through legislation allowing him as governor to intervene in the Terri Schiavo right-to-die case—and at the very end nearly triggered a showdown with a local judge by sending state police officers to seize her from a Tampa Bay area hospice.

With all this on his résumé, Jeb Bush is now considered a moderate? A RINO? What more can conservatives want?

***

It’s entirely possible that a big part of the “Jeb-as-moderate” meme comes from a simple lack of information. North of the Georgia line, how many people have had occasion to care about what Jeb did in Florida from 1999 through 2007?

After all, how many people outside Texas knew what George W. Bush had done in that state prior to 2000? For that matter, how many people even inside Illinois knew what Barack Obama had accomplished in the U.S. Senate prior to 2008?

In the absence of other information, a lot of assumptions about Jeb Bush, for better or worse, are based on beliefs about his father and older brother. The Republican base hears “Bush,” and they remember George H.W.’s broken “read my lips” promise on taxes. Or George W.’s prescription-drug entitlement and ballooning budget deficits and unpopular wars.

There are debates to be had regarding the fairness and intellectual consistency of some of these criticisms. After Ronald Reagan’s initial tax cuts, for example, he raised taxes way more than George H.W. Bush ever did but rarely caught grief for it, even back when he was alive. And the Republican base did not seem to object to George W. Bush’s Iraq War back in 2003—nor did it object to the single biggest driver of his budget deficits, his big tax cuts.

Setting that aside, though, there’s an easy solution to a lack of information. And as Jeb considers his nascent campaign and Republican activists begin to learn both about his accomplishments and the take-no-prisoners style in which he won them, they may well get over their doubts and accept him as their party’s conservative savior.

But what if they don’t? What if the Republican base demands of him exactly those things that he cannot give them?

At this week’s Wall Street Journal CEO Council meeting in Washington, Jeb outlined how he thinks a GOP presidential candidate in 2016 might have to embrace a “lose the primary to win the general” approach. He might have been speaking precisely about his party base’s two newest litmus tests—immigration and the Common Core education standards.

***

Jeb does not call himself the Outsourcing Governor or the Terri Schiavo Governor. He calls himself the Education Governor.

And key to that label has been his consistent advocacy through the decades for higher standards in public schools. True, pushing those rigorous benchmarks provides yet another club for pounding on teachers unions. True, higher standards also provide the moral and intellectual justification for awarding private school vouchers to students in the public schools that fail to meet those standards.

Yet even if unions had been on board with higher standards and vouchers had been off the table, Jeb’s statements and actions through the years suggest he would still favor more stringent academic standards.

He did not invent the statewide curriculum standards in Florida—the Sunshine State Standards had been completed under previous Gov. Lawton Chiles, a Democrat, under whose watch the state also began testing students regularly. But Jeb took that testing regime to a new level, and imposed new consequences for failure.

Similarly, Jeb didn’t invent Common Core. It came along after he had left office, the work product of governors and school administrators from all over the country. Yet he has embraced it and defended it through the years, even as it has become toxic for the Republican base that labels it “ObamaCore.” He did so again at last month’s annual conference hosted by his Foundation for Excellence in Education (although he pointedly extended an olive branch to those who disagree with him). Even if it were in his character to reverse himself on something he feels so strongly about, doing so now would likely create a bigger political problem for him than it would solve.

Immigration, if anything, is even less negotiable for Jeb. While education standards are a matter of principle, immigration is personal.

Jeb met Columba Garnica Gallo in León, Mexico, while he was on a senior-year service project from Andover. They were married three years later, mere days after he’d turned 21 and graduated from the University of Texas in just five semesters.

They lived for a couple of years in Venezuela, where he was able to use his Spanish daily in his work for Texas Commerce Bank, before they moved back to the States and eventually to Miami. Their three children share a dark complexion, and his elder son, George P., now the Texas land commissioner-elect, would suffer racial taunts as a kid on the baseball diamond.

In politics, Jeb has never seen his wife’s and his children’s Mexican heritage as anything other than a plus. He built the Dade County Republican Party from scratch, registering Latin American refugees and immigrants to vote as they emerged from naturalization ceremonies. Columba herself became an American citizen just in time to give a seconding speech for her father-in-law at the 1988 Republican National Convention. As governor, Jeb would often deliver statements bilingually, first in English and then in Spanish.

So let’s leave aside all the rational arguments Jeb makes on the topic—that immigrants bring vibrancy, specialized skills, even fecundity to this country. The important thing here regarding that nativist element of the Republican base, the one that occasionally strays over into overt racism: If the price of admission to the White House derby is to accept this group as a legitimate voice, then Jeb is not going to be interested in paying it.

***

There was a poignant moment 16 years ago at the Republican Governors Association meeting in New Orleans. George W. had just been reelected governor of Texas, and Jeb had won Florida on his second try. At a news conference, someone asked George about running for president in two years.

George W. tried dodging the question, and finally answered: “Listen, I didn’t grow up wanting to be president of the United States.”

And Jeb chimed in: “I did.”

To which George W. answered, “Yeah, you did.”

Yeah, Jeb did. From the time he was in grade school, as other kids growing up in Houston in the late ’50s and early ’60s might have dreamed of becoming astronauts, Jeb had dreamed of becoming president. There was, of course, one key difference: While the vast majority of the children in southeast Texas had no realistic chance of making it into NASA, Jeb actually had before him a plausible roadmap to 1600 Pennsylvania Avenue. His grandfather had been in the United States Senate, his father would soon be in Congress and was actively plotting the next steps toward the White House. There was every reason for Jeb to grow up thinking that with hard work and perseverance, he, too, could make it happen.

That was five decades ago. Now Jeb is 61, and he will turn 62 in February. If he doesn’t run this cycle, he likely will not have another chance. Should a Democrat (Hillary?) win in 2016, that would mean taking on an incumbent in 2020, never an easy task. If some other Republican wins in 2016, Jeb could not even try again until 2024, by which time he’ll be 71 and have been out of office nearly two decades.

It was this inexorable arithmetic that sent me out to National Harbor, Maryland, in mid-March 2013 for the annual Conservative Political Action Conference. President Obama had just been reelected a few months earlier. The Republican National Committee was nearly finished with its Growth and Opportunity report detailing what had gone wrong in the 2012 campaign. It would conclude, among other things, that the party had to improve its standing with minority voters generally, but particularly with the fastest-growing minority, Hispanics.

When I saw that Jeb Bush would be delivering the Friday night keynote speech, I made a point of attending. That he would get the invite was not a great surprise. At the time, the chairman of the group that hosts CPAC was Al Cardenas—the Cuban-born Miami lawyer and Jeb’s handpicked chairman of the Republican Party of Florida in his first term.

But Jeb had just released a new book, Immigration Wars, which concurred not only with the RNC’s autopsy report but also with many of the pieces that were making it into the Senate’s immigration package. Plus Jeb had in the past avoided CPAC and similar presidential hopeful cattle calls, so I was curious to see what kind of splash he’d make.

That evening was an eye-opener.

True, Jeb was rusty—nowhere near the top of his campaign game. He was stiff, hunched awkwardly, made eye contact mainly with the sheets of paper on the podium … but I’m not sure his presentation mattered in the least.

The audience was not remotely interested. Not in what he had to say, not in him. While Jeb talked about the importance of growing the party, they stirred their coffees and compared desserts. As Jeb explained why conservatives couldn’t just be against everything, they got caught up on their email and stepped outside to answer missed calls. A lot of the younger ones had already bailed out to get to a zombie-themed social gathering.

This was the same crowd that had been eating out of Texas Sen. Ted Cruz’s hand earlier. These were the same people who the next day would light up when former Alaska Gov. Sarah Palin joked about her rack. For Jeb? They could barely manage polite applause.

This week at that Wall Street Journal event, he trotted out similar rhetoric: “Republicans need to show they are not just against things but are for a bunch of things,” he said Monday at the Four Seasons in Georgetown, speaking to a very different type of audience. Whether the reception he gets in the weeks ahead is much different than he received last year from the activists is very much an open question.

***

But for the accident of election night 1994, all of this would be history already, Jeb’s history.

He was supposed to beat Democrat Lawton Chiles in Florida, while a thousand miles to the west, his elder brother was going to lose. A term and a half in Tallahassee, and it would have been Jeb beating Al Gore (winning Florida by a lot more than 537 votes, by the way) to become the 43rd president.

Two decades after that November night, the ground has shifted beneath Jeb’s feet. In 1994’s Republican Party, nobody was to the right of Jeb Bush. Today, there are all manner of louder, shriller voices in that party trying to redefine what’s meant by the word “conservative.”

So if the Republican Party is at a crossroads, Jeb Bush is right there with it. Down one path is a realignment with the emerging demographics of tomorrow. Down the other is a continuing retrenchment with the nation’s disproportionately older, disproportionately Southern, soon-to-be white minority.

As he said Monday in Washington, Bush didn’t know if he’d be a “good candidate or a bad one,” but a winning Republican campaign to him looked like this: “It has to be much more uplifting, much more positive, much more willing to, you know, to be practical now in Washington … lose the primary to win the general, without violating your principles. It’s not an easy task, to be honest with you.”

Here is the big irony: Of all the 2016 Republican names out there, Jeb Bush is uniquely positioned to make those connections with minority communities, particularly Latinos, while offering as conservative a policy agenda as can be imagined. He doesn’t have to make a production out of liking Hispanics—he for all intents and purposes is Hispanic. At the same time, his Florida record shows that he actually was the “severely conservative governor” that Mitt Romney told people he was.

And yet, because of the Republican activist base’s fixation with Common Core and illegal immigration, Jeb could find himself such a pariah in the early primary states that all the money and all the organization in the world cannot overcome it.

In his speech last month at his education conference, Jeb noticeably toned down his criticism of Common Core’s conservative opponents, telling them that he did not question their motives and suggesting they work together on those things they could agree on. After President Obama’s prime-time speech announcing his executive actions, Jeb responded on his Facebook page by denouncing Obama’s unilateral move—but then calling on Republicans in Congress to act on the issue.

In short, this is how far he’s willing to go: He’s willing to allow the existence of other views on Common Core, and to agree that Barack Obama is a feckless political opportunist when it comes to immigration.

It’s entirely possible that on these two issues of such great import to his party’s base, this is about as much reaching out as he can stomach.

Which sets up the first big question for a 2016 Jeb for President campaign: Will his party’s base let him get away with that?