Not the Bush You Think He Is Jeb Bush is more ruthless than he looks, more conservative than moderates like to believe, and possibly more appealing to Latinos than Marco Rubio.

Photographs by Mark Peterson

Jeb Bush at Manchester’s “Politics and Eggs” breakfast in April.

There’s a substantial gulf between the Jeb Bush who served two formidable terms as Florida governor and the man who’s recently earned himself gleeful comparisons to Dan Quayle. In fact, one could be more generous than that: There’s a substantial gulf between the Jeb Bush one sees on the primary-state pancake circuit and the man who, on national television recently, could not answer a simple question without inviting several dozen more. The Jeb Bush of town halls and Hampton Inn meet-and-greets is confident, alert, quick-witted: At “Politics and Pie” in New Hampshire, when a voter nervously began to ask, “Governor, having been the former governor of Florida — ” Bush cut him off: “You too?”

It took a moment for the audience to get it. The governor had just made a joke about a potential dangling modifier. Unlike his brother or his father, he doesn’t inspire panic that once he starts a sentence, he’ll never come out the other end alive.

But even before a bungled answer to a question about the Iraq War gave Jeb’s all-but-declared campaign the biggest headache of its unofficial history, people were starting to wonder whether the governor was equipped to handle the panoptic grind that American politics has become. At this stage, John Ellis Bush was supposed to be considerably ahead of the primary pack. He’s been hauling in money in giant lobster nets; he’s the Establishment favorite; and he moves through the world with the force of a thrown stone, applying his will with such adamantine determination that eventually the world curves back to him. This was supposed to be his moment. Or scotch that: Fifteen years ago was supposed to be his moment. Jeb was always considered the brighter Bush, and had he won his first gubernatorial race in 1994, it is likely that he, rather than his brother, would have been the GOP’s presidential nominee in 2000. In Tallahassee, where Jeb spent most of his brother’s presidency, some Republicans used to joke: We elected the Bush who went to Yale but acts like he went to the University of Texas; who we needed was the Bush who went to the University of Texas but acts like he went to Yale.

Instead of emerging as the inevitable candidate, the former governor finds himself in a Republican primary field of eight, and it could billow to as many as 15. Among the already declared is Marco Rubio, the freshman senator from Florida and one of Jeb’s former protégés. Jeb has underwhelmed the base — in Iowa, he polls in seventh place — and revealed himself to be far less polished on the hustings than his supporters had anticipated, particularly when answering questions that force him to navigate between family loyalty and a rational foreign policy. His one job above all else was to distinguish himself from his father and his brother, who rattle about Jeb’s campaign like a pair of unzappable ghosts. Yet when Fox News’ Megyn Kelly asked him whether he’d have supported the Iraq War, knowing what he knows now, the governor’s whiffing sequence of answers made clear he’d only thought through how to distinguish himself personally from his brother — by telling the story of his marriage, mainly, to a beautiful Mexican woman he’d met in León when he was still a high-school teen — but not politically.

Anyone who’s familiar with Jeb, though, doesn’t seem nearly as fixated on this episode as members of the national press corps. They know that freestyling is his natural political mode. As governor, Jeb genuinely enjoyed mixing it up with local reporters, almost always fielding more queries than his staff would have liked. “He’d do a five-minute gaggle” — mediaspeak for a mini press conference — “and you’d get five stories,” says Adam C. Smith, the political editor of the Tampa Bay Times. “He’d think out loud, he liked to banter. Compared to Charlie Crist, who never said anything, he was fun to cover.” But now, it seems, the very qualities that served Jeb well with the Florida press — spontaneity, authenticity — are serving him poorly on the national stage. Which is a shame, in its way: One of the pleasures of being around him, day to day, on the stump, is his enthusiasm for speaking off the cuff. (And I report this, it should be noted, as a person who agrees with exactly nothing the governor says.)

If it’s your custom (or source of pride) to work without a script, this habit is eventually going to pose a problem. It already did once for Jeb in Florida, during his first gubernatorial race: When asked what he’d do for African-Americans if elected, he replied, “Probably nothing.” (He lost.) In this way, Jeb’s candidacy has been the exact opposite of Hillary Clinton’s. She refuses interviews and carefully vets her questions from outsiders; he takes questions from reporters and potential voters alike, even if they’re attached to the tip of a poison arrow, and tries to answer them earnestly. Trailing him around New Hampshire, I was struck by what an enthusiastic technocrat he was, speaking in fusillades of facts and figures; he thinks nothing of replying to questions with the phrase “Let me give you a simple math drill.” (Had it been this Bush versus Gore, we would have been watching two iterations of the same man.)

It makes for quite a contrast to Rubio. Electric on a podium and blessed with a high-gigawatt smile, the junior senator from Florida is a master of telling uplifting tales of American possibility, and he can charm snakes from baskets. Rubio also represents a very different GOP. During the past eight years, while Jeb’s been absent from politics, a whole movement — the tea party — began to bloom. Yet rather than pandering to it, or even being mindful of it, the governor is running in outright defiance of the movement’s aesthetics and (in some very notable cases) intellectual preferences, as if it didn’t exist at all. This could be the biggest challenge Jeb faces, and it’s one entirely of his own making.

When asked if Loretta Lynch, Obama’s nominee for attorney general, should be confirmed, he answered that, yes, she should: “It shouldn’t always be partisan.” He has steadfastly refused to sign Grover Norquist’s pledge not to raise taxes. He has only slightly modified his views on Common Core, which the tea party despises — an irony given how many conservatives originally supported it, and how incensed the teachers unions were by Jeb’s radical education reforms. He talks passionately about legalizing the status of undocumented immigrants, which likely infuriates the tea party even more. Asked if he tips at Chipotle, where Hillary did not, he simply replies that he likes to make his own Mexican food. He leaves red meat on the table. And he seldom tosses it to audiences.

In December, the governor said that a successful GOP presidential candidate must be ready to “lose the primary to win the general.” It’s a deliberate paradox, niftily capturing the conundrum that most American candidates face when running for higher office: You can’t spend too much time appealing to the radicals in your own party during primary season. We are now watching Jeb live out this strategy in real time. The trouble is this strategy only works if you metaphorically lose, not if you actually do.

Bush and his wife, Columba, arrive at a town-hall meeting in May in Dubuque, Iowa. Photo: Charlie Neibergall/AP Photo

Drive down Columbus Boulevard in Coral Gables, and suddenly the Biltmore Hotel, a giant peach-colored castle, looms into view. It’s a suburbanite’s fantasy mash-up of the Alhambra and the Ducal Palace, the American-born love child of a Moorish princess and a Venetian doge. The lobby is framed by barrel-vaulted ceilings and marble columns and two giant wooden birdcages aflutter with finches; the irregularly shaped pool out back is the size of a lake. It’s just the sort of place one imagines would be ground zero for Florida politics. Countless senators and presidential candidates have buzzed through the joint; Rubio used to work out in its gym; and it’s where Jeb and his youngest son, Jeb Jr., currently have their offices. It is here that I meet with Jorge Arrizurieta, a longtime Bush-family friend and adviser who also keeps an office at the hotel.

“You have to understand. Jeb had a 64 percent approval rating when he left office,” he tells me as we sit down for lunch at the 19th Hole Bar & Grill. “And he had that kind of rating,” says Arrizurieta, “because he was respected more than he was loved.”

Jeb may come from one of the most storied political families in the United States. But to most Americans, he’s still a cipher. Though he spent from 1999 to 2007 governing the country’s third-most-populous state, he never had much of a national profile; voters outside Florida can barely summon a visual image of him, let alone the finer points of his personality or policies. The campaign was not entirely prepared for this problem. At home, Jeb was a king-size personality. As Al Cardenas, a Jeb adviser and former chairman of Florida’s GOP, told me: “One of the most difficult challenges for us has been how little people outside of the state know him. Leaving Florida has been a lesson in humility.”

Which is why it’s easiest to understand Jeb if one looks at him through the prism of Florida and, even more specifically, Miami. It explains his sensibilities (bicultural), his politics (particularly his views on immigration), his business dealings (especially their seedier side), and, perhaps most critically, his confidence in the face of lackluster polls and butterfingered fumbling.

It’s not just that Jeb was well respected here, as Arrizurieta says. It’s that he was considered extremely forceful and capable, which means competence is built into his self-image, no matter how clumsy he might sometimes appear as a proto-candidate. “He knew how to run the state government, I’ll tell you that,” says Carl Hiaasen, the Miami Herald columnist and best-selling novelist of delectable highbrow pulp. “Often with cold-blooded effectiveness. I disagreed with him on most things, but you knew who was in charge.”

One of the reasons Jeb accomplished so much during his tenure was a simple accident of history. The political scientist Matthew Corrigan explains: Republicans had control of both the governor’s mansion and the state legislature for the first time since Reconstruction; many of the legislators were new and eager to follow Jeb’s lead; and the state had recently begun imposing term limits, rendering lawmakers more inclined to engage with his initiatives rather than ride out his term until he went away. “And when you’re the son of a former president and the brother of a leading candidate, you just have a lot of sway,” says Corrigan, also the author of Conservative Hurricane: How Jeb Bush Remade Florida.

But the other reasons for Jeb’s effectiveness are characterological, not historical. He is stubborn, relentless, exhausting. Any moderate who’s considering voting for him ought to bear this in mind. Jeb may sound measured in tone, but he was hardly known around Tallahassee for his collaborative skills. “Jeb would rather charge the mountain and win,” says Dan Gelber, a former minority leader in the Florida house, “than downgrade to a hill and stand at the top with his former adversaries singing ‘Kumbaya.’ ”

Jeb mainly espoused a gentlemanly approach to dissent. But on occasion, he could be ruthless. When Alex Villalobos, a Republican state senator, refused to support an education initiative of his in 2006, Jeb stripped him of his position as majority leader and moved him to a minuscule office with only a TV tray for a desk. He tolerated few tweaks or amendments to his bills, even from members of his own party. At the First in the Nation Summit in New Hampshire this April, there came a moment when a voter stood up and asked Jeb: “What Democrats did you work well with?” He named two governors with whom he’d traveled to Iraq. From the state of Florida itself, he named no one at all.

What continued to earn Jeb grudging respect was his seriousness about policy. “It diminishes him a little to sum up his philosophy as ‘It’s my way or the highway,’ ” says Gelber, “because his way was pretty thought out.” He was quick on the REPLY button, volleying back emails to colleagues at all hours of the day and night. He inhaled information. “When you clashed with him,” says J. C. Planas, a Republican who worked with Jeb in the state legislature, “he always managed to read one more book than you had.” And he showed up everywhere. Florida got hit by a series of terrible hurricanes while Jeb was governor, and he always tended to them with alacrity, even when it meant skipping the 2004 GOP convention, where his brother was being nominated for the second time.

The result was one of the most radically conservative state governments of its day. He slashed taxes and the government work force; he tweezed out every stray bit of pork he could find in the state budget, earning himself the nickname “Veto Corleone,” as he never gets tired of saying. He ended affirmative action; passed the “stand your ground” gun law; and extended the long arms of the state into Terri Schiavo’s hospital room, trying to block her husband’s efforts to remove her from life support. He also enacted massive education reforms, imposing high-stakes testing in Florida’s public schools while creating two different voucher programs. “It was a fascinating experiment, what he did with education,” says Corrigan, though in his view, the results were decidedly mixed. (Reading scores among fourth-graders went up considerably but started to creep back down by the eighth grade.) “We don’t get that in government these days. Everything’s incremental. This was not incremental. This was a big change.”

Florida, from a political point of view, is a difficult state to subdue. Jeb has said it’s “as purple as purple can get,” but the state isn’t purple because it’s filled with political moderates; it’s purple because each part is radically different from the other. The panhandle and parts just below are still typically southern, while the Southeast is filled with liberal transplants from the Northeast (“The further north you go, the further south you get” is the old Florida saw). Only when you put the state on a spin-art machine and let it rip do the colors blur. Steve Schale, the Democratic strategist who ran Obama’s Florida campaign in 2008, notes, “It’s very hard to unify the state as a political figure. But you can do it as a personality.” This is what Jeb did, through an unlikely combination of studiousness, obstinacy, and nerve. And because he managed to do so — to unify a microcosmic version of the United States, with its polyglot mix of ethnicities and geographical refuges — it stands to reason he’d believe he has a shot at the presidency. Yet Jeb, the most conservative of all the Bushes, still can’t seem to make headway with the GOP base — and one of the foremost reasons is deeply personal, and therefore unlikely to change.

Neil, George H.W., Jeb, George W., and Marvin Bush in 1970. Photo: Newsmakers/Getty Images

“It doesn’t matter where we came from, or why we came.”

A narrator is speaking in Spanish. Different Latin American flags are waving in the breeze as he speaks. The Dominican Republic. Mexico. Colombia.

“In this land,” the voice continues, “we find opportunity, a better education for our children, the medical care our families deserve, a state that has opened its heart and has told us this is our house.”

Venezuela. Nicaragua. And then, finally, the state flag of Florida.

“We all want a better life.” This is Jeb Bush now, appearing onscreen. “Together, we are making it happen in this land, our home: Florida.”

He is speaking in Spanish. It is nearly flawless.

Jeb Bush made this campaign commercial in 2002. Thirteen years later, Sergio Bendixen, one of the best-known Democratic consultants to Latino candidates in the business, still shows it to focus groups. Doesn’t matter that it was made by a guy on the other side. He says it unfailingly makes at least one person well up.

“What he figured out,” says Bendixen, “is how proud members of each group are of their nationality and their culture. He knows that’s a magic formula.”

I had originally assumed, somewhat cynically, that Jeb Bush was not an honorary Hispanic but an honorary Cuban, representing solely the interests of Florida’s wealthiest group of Latin Americans. Not so, according to Bendixen and many others I spoke to: In Jeb’s days as governor, Latinos of all stripes liked him. When I ask Bendixen why, given that Hispanics have shown a demonstrable preference in surveys for expanding the role of government, he gives a simple answer: Jeb protected their dignity when others would not. “When Pete Wilson was the big leader of this huge anti-immigrant movement” — Prop 187 in California — “Jeb Bush and Giuliani were the only two Republicans who had the guts to say there was nothing to be gained.” Isaac Lee, the CEO of Fusion and president of news for Univision, says something similar: “When you say that a vast group of people — people who include your sister or your father or a close friend — should be electrified on a fence, nothing else is worth listening to because you’re being insulted.” So when Jeb starts talking about compassion toward immigrants, says Lee, “immediately, how he feels about big government is less important.”

Needless to say, this rhetoric does not endear him to the Republican base, the tea party in particular. Last year, at his father’s own library, Jeb went so far as to say that those who came to the United States in search of a better life for their children “broke the law, but it’s not a felony; it’s an act of love.” Yet Jeb has actually met with members of Congress (like Matt Salmon of Arizona) who are closely affiliated with the tea party in order to change their minds on this subject, says Clint Bolick, who co-authored a book on immigration with the governor. Luis Gutiérrez, the Democratic congressman who’s been trying in vain to pass comprehensive immigration reform on the Hill, recently declared that Jeb was the best Republican option Democrats had.

These efforts may seem quixotic. But how could one be married to a Mexican woman and live (and do business) in Miami and not be concerned about issues of immigration?

Jeb met his wife, Columba (known to everyone as “Colu”), as an exchange student in Mexico when he was just 17 years old. He married her less than four years later, at the University of Texas, where he majored in Latin American studies. His mother was not pleased, nor was his father always tactful about Jeb’s choice. “Remember,” says Joe Garcia, a Miami Democrat who briefly served in Congress, “he takes this personally. His own father referred to his grandchildren as ‘the little brown ones.’ ” A true story, from 1988.

Writing in The Atlantic, the author and former presidential speechwriter David Frum had perhaps the most insightful reading of Jeb’s marriage to Columba. He compared the former Florida governor to Barack Obama, of all people, noting that both men have “openly and publicly struggled with their ambivalence about their family inheritance.” He continued:

Both responded by leaving the place of their youth to create new identities for themselves: Barack Obama, as an organizer in the poor African-American neighborhoods of Chicago; Jeb Bush, in Mexico, Venezuela, and, at the last, in Cuban-influenced Miami. Both are men who have talked a great deal about the feeling of being “between two worlds”: Obama, in his famous autobiography; Bush, in his speeches. Both chose wives who would more deeply connect them to their new, chosen identity. Both derived from their new identity a sharp critique of their nation as it is.

As strange as it is to say, Jeb may be the true black sheep of the family, not W.

It’s not an accident that Jeb and Columba landed in Miami. The city, particularly the community of Coral Gables, is rivaled by few places in the United States for its Latin biculturalism. Columba is family-focused, highly private, and less comfortable speaking English than Jeb is speaking Spanish; scour the web and you’ll find almost no video footage of her, just enough to see that she has a gentle voice and stands a mere five feet tall. Jeb’s first run for governor in 1994 was reportedly very hard on her and their marriage, likely contributing to his conversion to Catholicism. When he won and moved his family to Tallahassee, she was miserable. It’s very hard to say what kind of First Lady she would be, given how limelight-avoidant she’s been. “She would take on domestic violence and anti-drug programs,” predicts Ileana Ros-Lehtinen, a longtime Miami congresswoman and supporter of Jeb’s. “But I don’t think she’ll dance with late-night-TV hosts.”

At home with Columba, Jeb speaks mainly in Spanish, which he refined during his three-year stint in Venezuela, where he opened a branch of the Texas Commerce Bank. Like many bilingual people, he thinks in his second language, not just speaks it, and it’s startling sometimes to hear him abruptly go to Spanish, mid-­sentence, continuing with the same verve. “When he switches from English to Spanish,” says Ros-Lehtinen, “he comes across as a warmer person. He’ll turn into a regular guy and not be so focused on being on-message.”

I’d had this very thought. Just over a month ago, while visiting Puerto Rico, the governor had been asked, in English, whether he’d ever attended a gay wedding or would consider doing so. He answered that no, he hadn’t, but “that’s not to say I wouldn’t.” He then followed up in Spanish with a much more forceful affirmation: Claro que sí. Of course he would attend a gay wedding.

Jeb’s biculturalism was likely key to his accumulation of power in the state. One of the now-obscure parts of his résumé is that he reinvented the Florida GOP, using the power of his name and connections to conscript many of the Cuban powerhouse politicians who now make up its spine. When Jeb first arrived in Miami in 1980, most of the Cuban politicos were Democrats, and they were getting nowhere in the primaries. Jeb soon took over the Miami-Dade Republican Party (“What a thankless job that was,” says Ros-Lehtinen) and turned it into a recruiting tool for Cubans, convincing them one by one that the GOP better represented their values.

Today, Cubans are not quite as influential in Florida politics. They are no longer the majority of the state’s Hispanic electorate. The new generation of Florida Latinos tends to lean more left than right, and even Cubans in the state have lately been tempted by Democrats, with 48 percent of them voting for Obama in the last election. Recent public-opinion surveys have made it clear that Hispanics overwhelmingly favor increasing taxes on the wealthy and increasing the minimum wage. Jeb does not stand for these ideas; Hillary does. She, too, is popular with Latinos.

But if presidential elections are won or lost in Florida, and if Florida’s electoral votes are won or lost based on the Hispanic vote, then Jeb, with his longtime celebration of those many, many flags, may be the only Republican candidate with a fighting chance to beat her. “Even Marco Rubio would be more limited to the Cuban base,” says Bendixen. Rubio, for better or for worse, is still affiliated with the anti-immigrant tea party. Plenty of non-Cuban Latinos remember his comment from 2009 — “Nothing against immigrants, but my parents were exiles” — and hold it against him, because it implied that those who came here seeking economic opportunity deserved less. (It has since come out that Rubio’s parents came here for economic opportunity themselves, rather than fleeing from Castro.) Ironically, it also turns out to be important that Jeb is not Latino. “Rubio is from the community,” explains Anthony Suarez, the president of the Puerto Rican bar association and a former state legislator. “But Jeb is not. He can say, ‘Immigrants are just other Americans.’ ” A gringo agitating on behalf of immigration rights — what could be more powerful than that?

There’s another problem that could spook Jeb this primary season, one that’s thornier in some ways than Common Core and immigration. Peter Schweizer, the author of Clinton Cash, says he’s been delving into the business transactions of Jeb Bush as well, and he plans to publish his findings online. Jeb prides himself on his business background. But a number of his deals over the years have involved a gallery of miscreants, making them hard to distinguish from the wild subplots of a Hiaasen novel. They’re pure Florida, in short.

“Well, yeah,” says Hiaasen when I ask him about it. “This is a place where Bernie Madoff did most of his damage. The state is a magnet for scammers and big talkers who can’t back it up.”

Getting rich quick is central to the Florida dream. The bankruptcy laws have historically been more lenient; the state has no personal income tax, which makes it attractive to professional athletes, retirees, scoundrels. Florida now leads the country in identity theft and mortgage fraud, and it’s also a hospitable climate for inspired Ponzi schemes. Politicians are constantly getting entangled — or at least roped into photographs — with swindlers.

“Here’s a classic example,” says Hiaasen. “If you go back, there’s a picture somewhere of Hillary Clinton posing with a guy who she was told was a legitimate man in the Florida Keys — what’s his name? He lived down the street from me.” He thinks for a second, fails to summon it. “Anyway, he was a big-assed dope smuggler. But he gave a lot of money, so he shows up at a reception in Miami, and of course he’s standing close to her, so she poses for a picture, because that’s what politicians do. God, what is his name?” Another pause. “Cabrera!” Yes. Jorge Cabrera, according to Google. “Anyway, I don’t know if he was bringing in coke” — 6,000 pounds of it, says the New York Times — “but the thing is, lots of people in the Keys knew he was in the business, because that was like a second industry down here. But how would Hillary have known?”

In the picture, she’s smiling with him in front of a Christmas tree.

“Or look up Scott Rothstein and Charlie Crist,” Hiaasen continues. “Scott was a big-time lawyer, a huuuuuge contributor to the Democrat Party — and the Republican Party. Mainly the Republican Party. He was running a giant Ponzi scheme.” South Florida’s largest, at $1.2 billion. “And Charlie Crist, in these pictures, he was practically nibbling on Rothstein’s earlobe.”

What’s different in Jeb’s case is that he wasn’t simply roped into unfortunate and ill-timed pictures with tricksters. Some of his entrepreneurial ventures involved the tricksters themselves. In the early days, before he was governor, his seamiest project concerned a company named MWI, for whom he brokered deals to sell water pumps overseas, including to Nigeria, where he traveled on the company’s behalf. The Justice Department later sued MWI, claiming it had given a Nigerian middleman $25 million to bribe officials in order to get government loans. (The governor was never implicated in the bribery, but a judge put MWI on the hook for civil penalties.)

Florida’s culture of get-rich-quickism probably held out a particular appeal to Jeb. It’s part of the Bush-family tradition to light out for the territory, reinvent oneself, and make one’s fortune before entering public service. Making money always comes first. Jeb’s grandfather left Ohio to become a banker in the Northeast. Jeb’s father left the Northeast to become a Texas oilman. W., by this standard, didn’t roll very far from the tree, but he did make money in the energy business and Major League Baseball before starting his political career.

Jeb, of all the Bushes, probably had the fewest assets before entering public office, and when he left Tallahassee, he was worth $1.3 million, which for the Bushes isn’t very much. His work space at the Biltmore is surprisingly unfussy (until January, he worked in a suite that didn’t even have its own bathroom). But the real-estate market went bananas during his time as governor. It must have whetted his appetite for a finer life. When I ask Howard Leach, one of Jeb’s most loyal fund-raisers, what the governor has been doing for the last eight years, he answers very matter-of-factly: “He’s been trying to rebuild his net worth.” And so he’s been sitting on corporate boards, doing real-estate deals with his son, hitting the speaking circuit.

He also got involved in what to my mind is his most eyebrow-raising venture. In 2007, Jeb became a consultant to a company named InnoVida, whose CEO claimed to have cheap, ready-to-build temporary homes for victims of earthquakes and other natural disasters. Later, he joined the company’s board of directors. There was just one problem: The CEO, Claudio Osorio, was lying. His business was largely imaginary. Eventually, an investor in InnoVida sued. Osorio pleaded guilty to fraud and is now in jail. InnoVida declared bankruptcy.

In court records, Jeb claims he was acting in good faith when he served as a consultant to the company. (He’s since returned $270,000, though the company’s trustees sought nearly $470,000.) His spokeswoman, Kristy Campbell, adds that the governor hired a former federal-law-enforcement agent to conduct a background check on Osorio and his company. “The report he received,” she says, “didn’t have any red flags that indicated criminal or financial wrongdoing.”

But Linda Worton Jackson, the lawyer who represented InnoVida’s creditors, points out that even the simplest form of due diligence — namely, consulting the internet — should have raised those red flags.

“A simple Google search would have shown that Osorio had already committed the same type of fraud,” says Jackson. It’s true: Even in 2007, it was possible to punch Osorio’s name into Google and find a lawsuit over a bogus electronics concern he’d founded. In fact, Osorio had been sued several times for fleecing investors before 2007. Had the investigator gone to the clerk’s office at the federal court in Miami, he would have discovered this, including a subsequent class-action suit against the electronics company, in which it was called a “fraudulent scheme.” And there were plenty of warning signs about Inno­Vida itself: Nine months before Jeb climbed aboard, a judge evicted the company from its factory space. One of its part owners had also been convicted of selling cocaine. “Jeb was paid $15,000 a month,” Jackson adds. “That’s a lot of money to be a consultant to a company you know nothing about.” To say nothing of being on its board. He attended at least two meetings. “You do not generally see politicians on the board of directors of a Ponzi scheme,” she says. “That’s what’s unusual here.”

InnoVida wasn’t a Ponzi scheme, exactly; it was just the sinkhole of a charlatan. Chris Korge, a board member and a prodigious Hillary fund-raiser, ultimately realized as much and sued. Jeb was the first person he contacted, and the governor reacted promptly, alerting the rest of the board and asking for financial documents. But it was far too late.

“Osorio entered into contracts with Haiti,” says Jackson. “He duped them out of millions of dollars after the earthquake. Can you imagine?”

So. Say what you will about Clinton Cash. Its findings now have the following competition: Jeb Bush served on the board of a company that bled the Haitian government — and big charities that served to help it — at just the moment its people, homeless and starving, needed it most.

I am sitting in the office of Norman Braman, the 82-year-old billionaire auto magnate in Miami who’s prepared to spend millions on Marco Rubio.

“I am offended,” he tells me, “by people who feel that they’re entitled to something just because of their last name.”

Braman is a formidable foe. He speaks about Rubio with the fondness of a father toward a son, and his distaste for the governor has personal roots: Back when Jeb was still in office, he vetoed $2 million in research funding for the Braman Breast Cancer Institute. (“Who the hell is against breast-cancer research?” Braman asked Politico, which first pointed this out.)

Out of curiosity, I ask if Braman has ever dealt with Jeb as a businessman.

“No.” Then he pauses. “Actually, he showed us a house once in Miami.”

What?

“It was many years ago. The late ’80s, I think.”

I tell him I never imagined Jeb actually showing houses as a young man in the real-estate business. That’s pretty small-bore. Braman smiles.

“It was a special house.”

Marco Rubio’s entry into the 2016 fray has been, to put it mildly, inconvenient for Jeb Bush. Rubio’s just behind Jeb in national polls, as is Scott Walker, and not by much. Almost all of the other candidates seem to have more Achilles’ heels than they do feet.

What this means is that the state of Florida could be central to the next presidential election in a way it hasn’t been since the days of hanging chads. The press down there is already having a ball with it. The Tampa Bay Times calls its coverage “Jebio.” An intra-Florida cage match would obviously make for a fascinating spectacle, in some ways eclipsing the psychodrama of even the Bush family itself. When Rubio was voted in as the speaker of the Florida house, Jeb presented him with a sword.

Gelber, the former minority leader of the Florida house, believes the friendship between these two men has been overblown by a press hungry for a soapy plotline. “Jeb wasn’t Marco’s mentor,” he says, his voice drenched with amusement. “Jeb was the general. All of those guys were lieutenants. Marco was an important ally, but he was fungible.”

But the governor is clearly still annoyed. At one of his impromptu press scrums in New Hampshire this April, a reporter started to ask, “Governor, Marco Rubio announced a few days ago —” and Jeb immediately interrupted, knowing exactly where the question was heading. “This is gonna be a 15-yard-penalty loss. This is a process question?”

“It’s not,” replied the reporter. “I’m curious if you felt betrayed at all —”

“That’s a process question!”

“It’s about your personal feelings!” protested the reporter. “It’s someone you were close with for a long time.”

Jeb paused, clearly not knowing what to say. Then, finally: “It is what it is.”

The governor may be reluctant to say anything negative about Rubio. But his advisers are less cautious. “Jeb has a fleet of friends who’d go through walls for him like no other candidate in the race, except maybe Hillary,” says Arrizurieta. “Marco doesn’t have that. Marco has never had that.”

He has a point. Jeb and the entire Bush clan have been around for so long that the governor has loyalists sprinkled all over the state, and most people who’ve worked for Marco worked for Jeb first — including Rubio’s 2010 campaign manager, who recently announced he’d be working as Jeb’s lead adviser for Hispanic outreach. Many state lawmakers who should be Rubio partisans are for the moment keeping mum.

But Rubio has other advantages when it comes to snatching up votes in his crucial home state. “The fact of the matter is that Rubio was on a statewide ballot more recently,” says David Custin, a Miami-based strategist. “There are millions of registered voters who’ve never voted for Bush. And there was no tea-party wing when Jeb ran. There is now, and Rubio connects to them.”

And it’s not just the tea party. “He’s televangical,” says Gelber. “And I always found it very maddening, because he was hijacking our issues and frankly sounding better than most of us. Rubio’s very good at sounding the right note. Whereas Jeb just always seems a little bit off-key.”

Most threatening of all, though, is that Rubio is a young man in a hurry with little to lose. Back in 2010, the world discouraged him from running in the Senate primary against Charlie Crist, and he didn’t listen then either. His biggest fear isn’t running for office too soon; it’s waiting too long, like Jeb. True, he had to give up his Senate seat in order to run. But he’s only 44 years old. He never cared much for Congress anyway. “He really feels that the Senate hasn’t debated the issues,” says Braman. Obama felt the same way. It was up or out.

Yet for all of Rubio’s and Jeb’s individual strengths, they both have substantial liabilities. In Rubio’s case, it’s precisely his resemblance to Obama that may undo him. The country’s already tried a bright, idealistic, rising Senate superstar, a fellow who was long on eloquence but short in the tooth, and it’s just this combination of inexperience and unrealized rhetoric that now disenchants Obama’s critics most. Jeb, meanwhile, has to eke out enough early primary wins to build the faith and momentum required to become the party nominee, and this is easier said than done: In Iowa, he polls disastrously, and the caucus spoils there have lately gone to religious conservatives anyway (Rick Santorum won in 2012). The governor’s best bets are South Carolina, which has a taste for Establishment candidates, and New Hampshire, where he’s already spent a lot of time — and seems to have figured out a shtick, as the guy from the tropics who’s suddenly forced to navigate the folkways of the Northeast. (“What are these things, by the way?” he deadpanned at “Politics and Pie,” pointing to a pair of old snowshoes mounted on a wall. “We don’t have these in Miami.”) Scott Walker, whom Iowa loves, could very well wind up trouncing them both.

Even if Jeb Bush makes it to the next trench — and then the next and the next and the next — he’ll eventually have to run against an extraordinarily well-funded candidate who just happens to be the first credible female contender for president of the United States, running with the full might of history in her sails. The Bush name and connections can reap a man many benefits — money, recognition, power. But the one thing they cannot do is turn back the clock. Jeb was a perfect candidate for 1994. He’d have been right at home in Newt Gingrich’s army of Republican revolutionaries as they took over the House in Washington and statehouses across the country.

His parents knew this. They had two sons running for governor that year. Jeb may have had the slightly tougher race, but they could have split up on Election Night, with one in Texas and one in Florida. Instead, I recently learned, they both chose to spend the night in Miami. As the evening wore on and it became clear that the Jeeves of the family had lost and the Bertie Wooster had won, they left and headed back to Texas. They could barely conceal their grief. (“The joy is in Texas,” George H.W. said, “but our hearts are in Florida.”) Five years later, George W. Bush was campaigning for president. Jeb was finally settling into the statehouse in Tallahassee.

So here we are, 16 years later still. George W. has poisoned the Bush-family name with a horrific war in Iraq, and the tea party has poisoned the GOP with its assault on rational discourse and nuanced policy. A charismatic bright young thing from the governor’s home state is nipping at his heels. Yet this may be Jeb’s only moment to jump into the fray. As blessed as he is, the ultimate political prize — lucky timing — seems to have eluded him in a way it never did his less talented older brother, even his father. But what can he do?

It is what it is.

*This article appears in the June 1, 2015 issue of New York Magazine.