Jeb Bush with a fan at the Chicago Council on Global Affairs in February.
Andrew Nelles—The New York Times

Read more: 51 Times a Bush has been on the cover of TIME.

Jeb Bush is running for the White House exactly 55 minutes at a time. That’s how long it takes him to march through quickie fundraisers that can rake in $150,000 an hour. Bush has the art of the ask scripted to the minute: he strolls into a friendly law firm or lobbying shop with a lone aide in tow, holds forth for 15 to 20 minutes, takes questions for 10 more, snaps a few photos and complains about the indignities of his paleo diet and his need for new suits. Then he ducks out the door and back into a car that whisks him to a new batch of benefactors. He can repeat this routine four or five times a day, a pace that most of his competitors have neither the network nor the hustle to match.

Since jumping into the race in mid-December, Bush has often netted a million bucks a day and sometimes more. He raised $2.3 million in Tampa on Jan. 26 and $4.2 million in Chicago on Feb. 18. At least six gatherings have come with $100,000-per-head price tags, including a soirée at a Park Avenue triplex in Manhattan. During a Feb. 17 trip to Washington, several hundred donors packed a house in the suburb of McLean, Va., paying up to $25,000 apiece. The hosts ran out of name tags. “It’s incredible,” marvels a longtime GOP bundler working for one of Bush’s rivals. “It’s just an ass kicking.”

Already this gusher of cash has chased Mitt Romney from the field, crushed Chris Christie’s momentum and sent a message to Hillary Clinton that Bush’s super PAC will set the pace in the dynastic clash looming next year. The former Florida governor is taunting Clinton in other ways as well. He coughed up gigabytes of government emails and hints that he will release up to 10 years of tax returns, creating a standard for transparency that Clinton is struggling to match. By the time Bush abandons the pretense about exploring a run and officially launches his campaign–which could be as soon as mid-April–allies believe his fundraising tally may approach $100 million, smashing the records set by Romney and Barack Obama four years ago.

And only a Bush could have done it. Jeb, 62, was bequeathed a standing army of elite operatives and rainmakers, a birthright nurtured by three generations of trench warfare and thank-you notes. It’s easy to grasp why the GOP’s grandees are lately smitten with the second son of George H.W. and Barbara Bush. A two-term governor of the ultimate swing state, Bush earned high marks for ushering in sweeping conservative reforms. He’s a Spanish-speaking wonk with a multicultural family that mirrors the nation’s metamorphosis, and he may be the only Republican with the mix of money, moxie and policy mastery to match Clinton.

But only if his surname doesn’t sink him first. After two Bushes in the Oval Office, even many Republicans are leery of a third. Dynasty has vaulted him to the front of the field, yet its handicaps could just as easily trip him up.

John Ellis Bush is so fundamentally a member of political royalty that the Bush brand is in his name twice. (His nickname is an acronym coined during his infancy by his mother, in deference to an older cousin also named John Ellis.) Since birth, he has been burdened, blessed and shaped by this legacy. The grandson of a Senator, the son and brother of Presidents, he experienced the kind of expectations that come from sharing dinners with two people who would run the free world. Forging his own identity was neither easy nor linear. He rebelled as a teenager, then found love young in central Mexico. In business, the family name helped him make millions. In politics, the determination to avoid old family mistakes contributed to an early defeat before he found his footing as a powerful governor.

Now, on the biggest stage of all, he must once again balance the best and worst parts of being a Bush. “It’s an interesting challenge for me,” he told a crowd crammed into a Detroit ballroom on Feb. 4 for the first speech of his unofficial campaign. “I’m going to have to do it on my own.”

But for Jeb Bush, it has never been that simple.

A Father’s Shadow

From the beginning, Bush was groomed for success. He was born in Midland, Texas, in 1953, a few months before his sister Robin died of leukemia at age 3. Soon after, the family moved to Houston, where his father was prospering as an oil executive. In 1967, Jeb’s parents pulled him out of a private high school in Texas to repeat ninth grade at Phillips Academy, the posh boarding school in Andover, Mass., where generations of Bushes have prepped.

Bush was adrift at Andover. He notched lousy grades and strolled the verdant grounds in a haze of pot smoke. At the height of Vietnam, he skirted the political turmoil roiling the campus. “I was a cynical little turd,” he said later, “in a cynical school.”

That changed one warm Sunday evening in the winter of 1971. It was the middle of his senior year, and Bush was sitting in a manicured public square in León, Mexico. Along with nine other students, he was spending 10 weeks living with a host family, teaching English and building a schoolhouse. His friend John Schmitz had started dating a local girl, and the couple pulled up to the curb of the Plaza Principal in his car to find Jeb.

Peering into the backseat, Bush laid eyes on 16-year-old Columba Garnica Gallo, the younger sister of Schmitz’s girlfriend. Bush likened the sensation to being struck by lightning. “Maybe it was just raw animal magnetism,” he told a reporter for the Miami Herald in 1986. “I can tell you the symptoms. Not being able to sleep. Not having an appetite. She was the first girl I ever felt that way about.”

Love transformed the aimless adolescent into a disciplined student. Jeb and Columba exchanged letters almost daily. Every six months, he returned to central Mexico to visit. His academic performance brightened: he made honor roll in his final trimester. He enrolled at the University of Texas in the fall of 1971 to be closer to Columba. Like his father, Jeb raced through college, majoring in Latin American studies and graduating Phi Beta Kappa in 2½ years in order to speed up the wedding.

The pairing of a son of privilege and a girl from Mexico who spoke almost no English was a new twist for the Bush family. Jeb’s father married the daughter of a publishing executive, a descendant of former President Franklin Pierce; his grandfather came from money and married into more. “How I worry about Jeb and Columba,” Barbara Bush wrote in her diary in 1973, shortly after helping Jeb pick out an engagement ring. “Does she love him? I know when I meet her, I’ll stop worrying.”

George H.W. Bush did not meet his son’s bride until the night before the wedding, in 1974, when they had dinner at an Austin restaurant called the Green Turtle. Jeb’s brother Marvin served as the photographer at the bilingual ceremony the next day, held in a small chapel on the UT campus. Only one image from the wedding survives, of a mustachioed Jeb, grinning in his tux and gray bow tie and towering over his bride. (The rest were ruined when Marvin mistakenly used rerolled film from a Frank Zappa concert, superimposing images of the Mothers of Invention over the Bush and Gallo clans.)

After graduation, Bush took a job at a commercial bank in Houston, but the culture was an uncomfortable fit for Columba. When he was asked to open a new branch in Venezuela, the couple jumped at the chance, living there for two years. Following his father’s 1980 presidential campaign, Jeb and his wife relocated to Miami, where Columba’s mother and sister-in-law had settled. The move had benefits for Bush as well. “I left Houston to get out from my father’s shadow,” he said later.

The Matter of Money

The desire to escape did not last long. It is a Bush-family precept that anyone called to public service must make his fortune first. “I’d like to be very wealthy,” Jeb told a reporter from the Miami News in 1983, “and I’ll be glad to let you know when I’ve accomplished that goal.”

Where his brother and father started as oilmen before turning to politics, Jeb jumped into the biggest bonanza South Florida offered: real estate. In 1979, while working as a traveling aide for his father’s first presidential bid, Jeb met Armando Codina, a Cuban-American developer who served as the Miami co-chair of the campaign. Codina began courting Jeb as a business partner, offering 40% of the proceeds in a fledgling real estate brokerage with no up-front investment. Jeb, who had no real estate experience up to that point, made around $40,000 his first few years. But in Miami a young man with nerve and connections could climb income brackets in a hurry.

The alliance with Codina led Bush into an unusually broad array of business ventures over the next 15 years. Bush leased office space and sold everything from golf courses to industrial sites to footwear. Some of these deals reaped huge returns, including a $1,000 investment in a downtown office tower in 1984 that Bush cashed in six years later for $346,000. As his reputation grew, he joined a series of corporate boards, including one for the Miami branch of a secretive Swiss-based bank whose office was a one-story home and that refused to accept deposits and never made loans. (Five years after Bush left the board, the bank was shut down by federal regulators for making investments contrary to its clients’ wishes.) Like his brother George, he would become a part-owner of a sports franchise, the NFL’s Jacksonville Jaguars, cashing out his small stake in the team in 1997 after four years. “Jeb is a very strong, insightful businessman,” Codina wrote in an email to Time. “He has a very strategic mind, and I give him full credit for the success of our real estate brokerage and management company.”

As his father had done in Houston, Bush moonlighted as a local Republican chairman in Miami. The South Florida GOP was then divided between a moderate establishment and a more conservative band of Cuban Americans. Bush marshaled the support of both, raising money and displaying a willingness to pepper his father’s staff in Washington with requests for small favors. His reputation and connections earned him an appointment by Governor Bob Martinez as Florida’s secretary of commerce.

Bush was soon besieged by businessmen who wanted to make government contacts and thought the son of a Vice President could provide them. That role was fraught with peril. Miami was a frontier town in the 1980s, the de facto business capital of Latin America. In a state known for flamboyant figures, it was often hard to discern which moguls were spotless and which were seamy. “Florida is Florida, and Miami is even more Florida,” explains Mac Stipanovich, a Republican lobbyist in Tallahassee who ran Bush’s first gubernatorial campaign. “It’s hard for almost anybody to do business there without occasionally finding out that one of your partners is not who you thought he was.”

In the mid-1980s, a Cuban-American businessman and GOP fundraiser named Miguel Recarey hired Bush to find office space in South Florida for his fast-growing health-maintenance organization. Recarey asked Bush to call a Medicare official who had worked under his father to urge “fair treatment” for the company. Bush’s real estate firm was paid a $75,000 fee by Recarey, though it never leased the office space. Within two years, the company was shut down for insolvency; its owner fled the country to avoid federal fraud charges. Later, Bush drew unwanted attention when a company he was affiliated with came under federal indictment for allegedly concealing payments made to grease a deal to hawk irrigation pumps in Nigeria. Bush was never accused of any wrongdoing. But as he later told the St. Petersburg Times, “I have to have better radar.”

By the time he ran for governor in 1994, Bush was worth more than $2 million–good but not great by family standards. “His record in business shows two things,” says a party veteran who otherwise praises Bush. “He hasn’t had great success. And a couple of things he did raised questions about his judgment.”

King Jeb

If few were surprised when Bush decided to run for governor in 1994, the edgy chords he struck in that race were another story. It was the year of the Newt Gingrich revolution, and Jeb, who had watched much of his party’s base abandon his father two years earlier, positioned himself as a “headbanging” conservative who wanted to “club this government into submission.” He ran ads criticizing the Democratic incumbent, Lawton Chiles, for not signing enough death warrants; called for the abolition of the Florida department of education; and carped about gay-rights activists and other “modern victim movements” seeking special entitlements. Asked what he would do for the state’s black population as governor, his answer included the phrase “probably nothing.”

Bush lost by 64,000 votes, a margin of less than 2%. At 41, with three kids, he had missed a chance to win the governorship of his adopted state. The defeat echoed the missteps of his father, who lost in his campaign debut in part by veering too far right. Meanwhile, his older brother surprised even his parents by winning the Texas governorship that same year.

Jeb never stopped running. The day after the election, he woke at 6 a.m. on three hours’ sleep to stand at a Miami intersection and thank passersby for their support. Biding time for a second try, he created an education think tank called the Foundation for Florida’s Future and helped launch the state’s first charter school in a blighted section of Miami.

Bush has been telling audiences this year that the 1994 defeat taught him the importance of empathy. “I had these deeply held views about education, for example, but people didn’t connect with me,” he told the audience in Detroit last month. He spent the next four years visiting more than 250 schools in Florida, almost always without staff or press in tow, and kept a journal of his encounters, emailing excerpts to advisers. He spent so much time in the classrooms that he became a godfather to a young black boy.

When he ran again, in 1998, he spent hours on the stump talking about how school choice could remedy the plight of the poor. He became a smoother public speaker and skirted the controversies that ensnared him four years earlier. “He took that time to reflect on how he spoke and how he articulated his positions,” says Florida state senator Anitere Flores, who worked on both Bush campaigns before becoming his top education-policy adviser. “He came back the next campaign a lot stronger.” He won the race in a rout.

Once in office, Bush set to reshaping Florida into a model of conservative governance. He pioneered “stand your ground” gun laws, slashed taxes and battled the state’s public-sector unions. “Before Scott Walker was fighting public unions, the public unions in Florida couldn’t stand Jeb,” says Matthew Corrigan, a political scientist at the University of North Florida. “This guy had big ideas, got them through the legislature, got the money appropriated for them and then followed up on them. He sent emails to low-level bureaucrats telling them to do things this way.”

Bush promoted school choice and pushed through a controversial plan to end affirmative action in public universities. He whittled away at the state’s sprawling bureaucracy, privatizing everything from prison meals to the Florida human-resources department. In his second inaugural address, in 2003, the governor rhapsodized about his fantasy of gutting government. “There would be no greater tribute to our maturity as a society,” he declared on the steps of the capitol, “than if we can make these buildings around us empty of workers–silent monuments to the time when government played a larger role than it deserved or could adequately fill.”

Dubbing himself the “most pro-life governor in modern times,” he probed the limits of executive authority in an attempt to curtail abortions. He convened a special session to pass legislation restoring the feeding tube of Terri Schiavo over the objections of her husband. The brawl made him a hero to the right-to-life movement; critics christened him King Jeb. But even some opponents describe the man who steamrolled them with grudging respect. “Every time I hear about him being a moderate, I start to laugh,” says Dan Gelber, a former Democratic state senator. “Jeb is not a populist. And he’s not a demagogue. Some of his policies were very unpopular, and he pursued them anyway. He’s not one of those guys who wants or needs to be loved. He knew what he wanted, promoted it aggressively and rarely lost.”

Part of the reason was the sheer amount of time Bush spent hunched over his laptop. If his father’s leadership style was rooted in relationships and his brother governed from his gut, Jeb put his faith in his ability as a manager. “If you give him a report that was commissioned a year ago, he actually reads the damn thing,” says Stipanovich. “If you’re staff, it can be very unnerving.” Friends describe a family man with bottomless drive and a taste for competition. “He would have events from 7 a.m. till 10 p.m.,” says his longtime friend Al Cardenas, a former chairman of the Florida Republican Party. “Then he would get on phone calls and write personal notes.” On Sundays, Bush often races through a morning round of speed golf (a habit he picked up from Dad), then heads home to read reports and tackle his email.

As governor, Bush sent so many emails that his official portrait hanging in the governor’s mansion includes his ubiquitous BlackBerry in its cradle. A trove of correspondence, released this winter in response to public-records requests, draws a portrait of a leader who rose early, stayed late and relished the minutiae most governors delegate. He made his address public (jeb@jeb.org) and devoted about 30 hours each week to thanking well-wishers, soliciting policy ideas, even sparring with hecklers.

Jeb has always been more substance than style, a technocrat who doesn’t often display his brother’s gift for gab. “He doesn’t like the backslapping of politics,” says T. Willard Fair, the CEO of the Miami Urban League and a longtime friend who teamed with Bush to build Florida’s charter-school network. “If you could put him in the corner with a book, he’d rather do that.” Even close friends say he doesn’t kibitz much, charging through pleasantries on the phone to cut to the heart of the matter. But he has mastered the niceties that count in campaigns, like entering donors’ numbers into his personal cell phone so he can greet them warmly when they call.

For a politician who operates as a soloist, Bush has built an ensemble of allies with rare devotion. The ardor was clear on a Tuesday afternoon in mid-February, when 300 longtime supporters showed up at a Tallahassee hotel with a view of the state capitol for a fundraiser to benefit Bush’s super PAC. Lobbyists and former aides wearing circular red jeb! ’16 stickers on their chests scribbled out checks on tall cocktail tables as they waited to enter a ballroom with baubly glass chandeliers. “There are a lot of us who would do almost anything for him,” says former Bush political director David Hart, pulling from his pocket an index-card-size printout detailing the state’s education gains since Bush took office. “There’s a million moments that I hope I’ll never forget.”

(Not) Enough Bushes

Dynasty may seem like destiny for Bush now, but it didn’t always look that way. When Jeb left Tallahassee eight years ago, the Bush brand was in tatters as his brother’s presidency limped to its conclusion. Until recently the prospect of a political resurrection looked bleak. “We’ve had enough Bushes,” Barbara Bush declared in 2013. If Jeb ran, she noted, he would inherit “all our enemies, half of our friends.”

That was probably a bit of sly misdirection by Barbara, who is no slouch at political messaging. But it is true that the obstacles to a campaign went beyond the foreign policy misadventures of his brother, his father’s failing health and his mother’s seeming doubts. There were also the complications of the family he created. His daughter Noelle had struggled with drugs. And the long journey from León, Mexico, to the statehouse in Leon County, Florida, had long been rocky for Columba.

“No one prepares you for a life in politics,” she wrote in a 2003 essay for a book about Latina mothers. “We live under so much pressure … we have crisis after crisis after crisis after crisis.” During Jeb’s first gubernatorial run, their marriage nearly buckled under the stress. In an effort to mend things, Bush converted to Catholicism in the mid-1990s and scaled back his travel schedule. Never a fan of the limelight, Columba had receded further since being stopped at customs in 1999 with $19,000 worth of undeclared luxury goods picked up while shopping in Paris. She prefers meals or margaritas in Miami restaurants to the stuffy galas typically required of a political spouse. But friends say the partnership works, however unconventional it may seem. “Other people may have doubted Columba’s support,” says Ana Navarro, a Florida Republican operative. “But I don’t think Jeb ever did.”

As Bush sought his wife’s blessing, the family brand was slowly rising from the ashes. The 43rd President’s biography of the 41st, coupled with a hagiographic HBO documentary, formed the core of a quiet campaign to stoke nostalgia for the first Bush presidency and thaw opposition to a third. At the same time, Obama’s struggles to tame Islamic extremism refired the Restoration instincts in Republican politics. By June 2014, George W. Bush’s approval rating trumped Obama’s in Gallup polling, breaking the 50% threshold for the first time in nearly a decade.

And so a year ago, Bush asked his top political advisers to map out a role in the 2014 midterms with an eye toward a possible presidential run. As he campaigned for Republican candidates, he met privately with policy bigwigs. He had his fundraisers gin up cash for key governors, always a good way to test the waters around the country. Brother George began to lobby him privately and for him publicly, telling one gathering of family retainers that the brand name was no longer an obstacle. “What’s the difference if it’s Bush, Clinton, Bush, Obama, Clinton,” he asked, “or Bush, Clinton, Bush, Obama, Bush?”

There is little doubt which President Bush Jeb prefers. “Imagine what it would be like to be Michael Jordan’s son going out to play basketball,” he told Esquire in 2008. Just last month, Bush declared his dad “the greatest man alive” and joked that he would step outside to fight anyone who disagreed.

The relationship with his brother is more complicated. The two have never been close. Separated by 6½ years in age and a similar gulf in temperament, they grew up in different places (W. in Midland, Jeb in Houston), made their fortunes in different states and gravitated toward different religious traditions. Nor was it any secret which son the parents expected to carry the family’s political torch. “The heir,” says one longtime family friend and adviser, “was clearly Jeb, not W.”

The scars of sibling rivalry aren’t hard to spot. On election night in 2000, when word came during dinner in Austin that George W. appeared to have lost to Al Gore a battle that Jeb was supposed to have wired in Florida, the younger brother tearfully apologized. Jeb has boasted about staying faithful to his brother when other Republicans turned their backs. “Until death do us part,” he told CNN in 2010. But as Jeb mulled a presidential campaign last year, George W. was left to interpret the smoke signals from the outside, like most everyone else. Politics is complicated, family even more so.

From his townhouse outside Miami and his nearby office suite at the palatial Biltmore Hotel resort, Jeb watched rivals like Christie and Marco Rubio slip and stumble through 2014. Soon he was telling key donors to “keep [their] powder dry.” By early summer, longtime political allies began quitting their day jobs or taking unplanned sabbaticals. His family, including Columba, came on board. “I hope he runs,” George W. Bush told CBS News in November, pegging the odds at 50-50.

But even before then, friends had begun to prod him privately to make up his mind, lest he earn a reputation as the Hamlet of Coral Gables. Inside the family, the advice got more specific: Don’t wait too long. In the official version of events, Bush made the final call over food and football on Thanksgiving weekend, surrounded by family–including his oldest son George P., the Texas land commissioner who is viewed in the family as the great political hope of the next generation. Jeb told his political advisers the following Monday. “When you look back, you can see that he knew,” says a longtime friend. “But at the time, he kept it hidden.”

Once Jeb committed, the Bush clan was “all in,” says a family member. Its vast universe of operatives, retainers and moneymen responded as if the bat symbol had been beamed into the sky. On cue, Barbara Bush sounded the all clear: “What do you mean there are too many Bushes?” she said. “I’ve changed my mind.”

His Own Man

And so the Bush money machine is cranking back up again, the seventh go-round in 35 years. It is virtually certain to win the GOP check-writing contest; there remains the matter of proving that the candidate can win votes. From temporary offices vacated by a law firm in Tallahassee, advisers are plotting his path to the nomination. As his team sees it, Bush has four main weaknesses among primary voters. He is a longtime champion of comprehensive immigration reform in a party suspicious of amnesty. He supports Common Core education standards, which have emerged as a grassroots bugbear. His refusal to sign antitax pledges calls up for skeptics the “read my lips” promise broken by his father, and his recent statement that conservatives should respect gay couples who marry made social conservatives skittish.

Then there are the liabilities of his lineage. The conservative base came to regard George W. Bush as a Big Government Republican, a profligate spender who ran up big deficits, passed now-unpopular policies like No Child Left Behind and Medicare Part D and presided during the greatest economic crash since the Depression. Many presume Jeb is much the same. And polls and party operatives agree that in the coming battle against Clinton, the party would benefit from a fresh face.

Few people outside Florida know much about Jeb, and his advisers acknowledge that the campaign’s success may hinge on its ability to distinguish the new family man from the Bushes who have preceded him. (It is no accident that the candidate’s signage and swag don’t include his last name.) But at some point this may require a public break from his brother. Jeb–who supported George W.’s wars and has argued that Obama’s troop withdrawal paved the way for the rise of the Islamic State of Iraq and Greater Syria (ISIS)–gently conceded during a recent appearance in Chicago that his brother had also made mistakes in Iraq. But the muscular foreign policy vision he laid out left audiences wondering exactly how his approach would differ.

On the last Friday of February, Bush finally waded into his first actual campaign scrum. It was no lovefest. The Conservative Political Action Conference, held at a hotel on the frozen banks of the Potomac outside Washington, is an annual confab dominated by the party’s young and libertarian-leaning activists. The event is a bad forum for picking Presidents but a good gauge of the grassroots zeitgeist. And the verdict was clear: Bush wasn’t one of them. Before he spoke, talk-radio host Laura Ingraham inveighed against the resurrection of the dynasty. “The idea that we should be conducting any type of coronation in the Republican Party today because 50 rich families decide who they think will best represent their interests? No way,” she said. When he took the stage, a cluster of Tea Partyers clad in revolutionary garb started a “No more Bushes!” chant out in the hallway.

Jeb offered a glimpse of how he will try to disarm his doubters. He rattled off his conservative reforms in Florida, defended his support for immigration reform and tougher education standards, and joked about killing so many spending bills he earned the nickname Veto Corleone. And most important, he weathered the intermittent heckling and boos with good cheer. “For those who made an ooo sound–is that what it was?” he asked. “I’m marking you down as neutral, and I want to be your second choice.” He had walked into the lion’s den and emerged unbowed.

When it was over, he repaired to a smaller ballroom to greet supporters, who had been bused in from D.C. by former aides of his brother’s. Fans in Bush regalia handed over their information to his PAC as they lined up to enter the room. The soon-to-be candidate entered through a black curtain to the soaring theme from Rocky. “That was raucous and wild,” he declared from the rickety stage, “and I loved it.”

It was an early glimpse of how Bush will fulfill his promise to run the grinding marathon of a presidential campaign “joyfully.” Surrounded by friends of the family, he shook hands and snapped selfies, smiling like a man who was exactly where he thought he belonged.

Write to Alex Altman at alex_altman@timemagazine.com.

This appears in the March 16, 2015 issue of TIME.

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