Florida's Democratic gubernatorial candidate Andrew Gillum attends a campaign rally where he received the endorsement of three major national, state and regional LGBT groups on Sept. 24, 2018 in Miami. Gillum has held varying polling leads in the preponderance of general election surveys, with a few showing his advantage as high as between five and seven points, a margin that would amount to a blowout in normally too-close-to-call Florida and unprecedented for any Democrat in memory. (Joe Raedle/Getty Images)

Fueled by his defiance of political norms, Andrew Gillum is on the cusp of history in Florida.

Andrew Gillum's first serious act of political defiance came 18 years ago when he crashed the office he's now on the cusp of occupying himself, confronting a governor by the name of Jeb Bush.

Just a 20-year-old college sophomore at the time, Gillum was one of four students who stormed the governor's office in Tallahassee and vowed to wait as long as possible to push for changes to Bush's plan to dismantle affirmative action preferences.

With hundreds of chanting students circling the rotunda outside in protest, Bush quickly granted not only a meeting, but a few substantive concessions – promising the measure would be reviewed every three years and pledging support for legislation to pay for SAT preparatory courses for disadvantaged high school kids.

Gillum emerged claiming a step in the right direction, but also unfulfilled.

"I think that we accomplished something," he told reporters afterward, adding, "Let there be no mistake. We are not satisfied with our progress."

From the start, Gillum's underdog campaign for governor of Florida was always predicated on the same unsatisfied defiance that fueled his earliest days as an activist. To those who have known and watched him closely, his gift of personal magnetism, commitment to advocacy and unyielding ambition made him destined for this moment.

And yet when his name first floated publicly as a gubernatorial candidate, he was told all the reasons it wasn't feasible.

Geography: He's from Tallahassee, one of Florida's smallest of 10 media markets and therefore one of the hardest places to gain statewide name recognition and marshall resources.

Demography: Even Democrats had never in their history nominated a black man to become the state's chief executive.

Ideology: With positions like Medicare for all, restrictions on guns and the legalization of pot, he was assumed to be too liberal for the king of all swing states and the adopted home of President Donald Trump.

So to say what he's trying to do has never been done before is not just overhyped political jargon. That he now stands as the nominal frontrunner to become the first Democrat in 24 years to win a governor's race in Florida – and the first African-American ever to do so – is uncharted territory in itself, and if he's successful, it will be one of the most consequential results of this 2018 campaign cycle. He will immediately become one of the most important Democrats in the country and regarded as an emerging national star of a party bending to the left.

"When they tell me I can't be something, they only fuel my fire," Gillum says in an interview with U.S. News from his campaign bus just days before Election Day. "When they say it's not possible, it only gives me more motivation to prove them wrong."

But now, the question in Florida is no longer if Gillum can win. In these final days, it's become: Can he lose?

"There's something Kennedyesque about Andrew. People don't really know why – they just feel good," says Gary Yordon, a television producer who helped film Gillum's first campaign commercial for Tallahassee city commissioner 15 years ago. "The last five or six candidates [Democrats] put up for governor, they've been like oatmeal – nobody to get excited about. Andrew's like steak and eggs."

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Andrew Gillum leads a prayer in the Liberty City neighborhood of Miami, where he spoke with residents about gun violence and quality of life on Aug. 13, 2018. (Lynne Sladky/AP)

It's the day after the final gubernatorial debate and Gillum is on a stage inside an auditorium at Florida Memorial University, where he's lamenting the campaign's nasty devolution to an assembly of revved up black students.

"At one point, I started to feel bad for him," Gillum says to laughs. "He had my name all down his mouth . . . And then he couldn't put respect on it."

Gillum is referring to his Republican opponent, Ron DeSantis. The 40-year-old DeSantis was a three-term, Trump-cheering congressman from Jacksonville who resigned his post last month to focus wholly on the gubernatorial race, where he's been clawing from behind since August. A sharply skilled debater, the Harvard and Yale educated DeSantis has largely centered the final weeks of his campaign around attempting to disqualify Gillum as a corrupt, tax-raising socialist who will imperil the state's growing economy and fail to keep Floridians safe. A GOP operative involved in the DeSantis campaign says the predominant theme is: "Andrew Gillum is damn scary."

But it was in the hours after he clinched the primary that DeSantis made the calamitous mistake that put him behind the eight ball. Appearing on Fox News, DeSantis warned voters not to "monkey up" the state by voting for Gillum, a charge widely perceived as a racial epithet.

No matter how it was intended, the comment set an ugly tenor for a campaign where race has been wielded in blatantly bigoted attacks by outside extremists and more obliquely in questions about Gillum's record on crime and personal ethics.

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Gillum would become only the fourth African-American governor in the nation's history, following Virginia's Douglas Wilder, New York's David Paterson and Massachusetts' Deval Patrick. While he has stopped short of branding DeSantis a racist, he believes his opponent has "doubled-down on talking about race."

"There are clearly racist elements trying to help him win," Gillum says. DeSantis has accepted thousands of dollars from a Republican activist who has used the N-word to describe former President Barack Obama and has appeared at conferences that have promoted the belief that African-Americans owe their freedom to white people and that whites are actually the victims in the race war.

In the final debate, DeSantis demonstrated exasperation at being held responsible for every supporter's remarks: "How the hell am I supposed to know every single statement someone makes?"

But Gillum says he doesn't need to "call [DeSantis] a name, I just need to cite his record."

Trump, who will appear in Florida with DeSantis twice in the final week before the election, called Gillum "a thief" on Monday. And as DeSantis attacked Gillum during a rally in Coral Springs later, the crowd chanted "Lock him up!"

Gillum has clutched to varying polling leads in the preponderance of general election surveys, with a few showing his advantage as high as between five and seven points, a margin that would amount to a blowout in normally too-close-to-call Florida and unprecedented for any Democrat in memory. But in the interview, Gillum dismissed this reporter's description of him as the front-runner.

"I haven't presumed myself to be the favorite. I presumed myself to be in the fight of my life," he says. "Florida is a 1 percent state. It will likely come down to fewer than 1 percent of the votes in this state who will decide the next governor, so I've gotta go and get those votes."

Still, he adds, "I feel like we're going to win."

Susie Wiles, the chair of the DeSantis campaign says Gillum deserves his due. "He's an exciting, different kind of candidate for Florida. There becomes an early cachet around some candidates and that's what we're seeing here."

"It doesn't mean it holds to the end," she says.

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People react as Andrew Gillum speaks during a campaign rally at the International Union of Painters and Allied Trades on Aug. 31, 2018 in Orlando, Florida. (Joe Raedle/Getty Images)

Born in Miami as the fifth of seven children, Gillum grew up poor. His mother drove a school bus, pressed clothes at a dry cleaner in the summer and cleaned homes on the weekends. His father, who struggled with alcoholism, worked construction and sold fruits and vegetables on the street corner. With several of his older brothers getting in trouble with the law, his father's advice to him was that if he kept his record clean, he could be admitted to the military.

As a teenager Gillum became engrossed by the NBC show, "A Different World," a spin-off from "The Cosby Show" that featured a cast of African-American students and their lives at a fictional all-black college in Virginia. It was the first instance Gillum ever saw of people who looked like him succeeding academically, thriving socially and on the path to big careers. It changed what he thought was possible.

"In spite of the fact of my Dad telling me that if I did well, I could go to the military, I said, 'No, I want to go to college,'" he recalls.

In 1992, his family moved from Miami to Gainesville for a fresh start and to be closer to Gillum's grandparents. It is there where he met Chris Chestnut, the only other African-American in his class, whose mother was a member of the Florida legislature and the first African-American woman to be elected mayor of Gainesville.

Gillum began hanging out at Chestnut's house and steadily became immersed in political conversations prompted by Cynthia Chestnut.

"She took me under her wing and . . . I just got increasingly interested," Gillum recalls. "She had me come up to the Capitol so I could be exposed to the legislature. We were just really overexposed to the political process."

Determined to break his family's cycle of intergenerational poverty, Gillum became the first in his family to graduate high school and go on to college in Tallahassee, in part because he saw that location as where the action was happening.

Gillum ventured two and a half hours west to attend the historically black Florida Agricultural and Mechanical University, where he quickly became known as a curious and persuasive student leader. He mobilized his fellow students to protest for voting rights for people who had been removed from the official rolls and spearheaded the affirmative action meeting with Jeb Bush.

Later that same year, it was Bush's brother's narrow presidential lead in Florida that prompted another Gillum-inspired protest as a recount over hanging chads and indecipherable ballots dragged out for weeks.

"Nobody wanted to do that," recalls Melanie Newman, a classmate and friend of Gillum's at Florida A&M. "We were tired. We felt defeated. We felt like we didn't have enough of a voice. And Andrew held a meeting, he invited people who had trouble voting to share their experiences. A lot of people showed up and he put together a strategy."

"Going into the meeting, it was like, 'Oh Andrew, always trying to do something. We gotta talk him out of it.' And Andrew was always like, 'We don't have to take what they give us.'"

It soon became clear that his senior year stint as student government president and forthcoming political science degree were not merely resume-building exercises. Gillum began closely tracking the actions of the Tallahassee City Commission, which passed an ordinance limiting the number of students who could occupy a house at the same time.

Gillum saw this as housing discrimination and organized a group of students to protest the move at a meeting. He felt like some of the commissioners weren't taking them seriously.

"One commissioner said, 'Students are like house guests. We love to see you come, but can't wait to see you leave!' They broke into laughter," he recalls. "I just remember thinking, 'Oh no they didn't.' We fuel this economy and we came here to let our voices be heard and they completely disrespected us. And I decided, you know what? I'm going to take one of them out. That moment of disrespect," he pauses, "told me I had to do something about it."

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Gillum speaks during a campaign rally held at the University of South Florida on Oct. 22, 2018 in Tampa, Florida. (Joe Raedle/Getty Images)

With his collegiate coursework completed, Gillum mounted a campaign before graduating Florida A&M and won – at age 23, becoming the youngest person to be elected to the Tallahassee City Commission. It was the same year John Marks, who is also African-American, became mayor. Gillum's campaign was, essentially: Give a kid a chance.

"There was a need for something different in the city of Tallahassee and we both brought that to the table," Marks says. "He did not hit the ground running. There was a learning curve there. Even I had a learning curve."

Marks recalls Gillum largely keeping his head down during his first few years, learning the agenda items and procedures and dealing with the intricacies of a billion dollar annual budget.

Gillum acknowledges now that at the beginning of his commission tenure he had moments where he doubted whether he had what it took to make decisions to lead a city. As he visited African-American churches for constituency outreach, most people were supportive and provided polite encouragement, simply proud to see another black face on the dais. But on one Sunday, a woman approached him with a message that stung.

"I'm disappointed in you," she told him. "I watch those city commission meetings and I wait every week to hear what you have to say. And you don't say anything. You don't speak up."

Gillum says it's that single conversation with a woman in a church that prodded him to be more assertive. "It sort of unleashed me," he says.

Few local officials bring game-changing ideas to city hall, but Gillum was an aggressively reactive commissioner, assiduously responding to people's problems and requests. Throughout his time there, Gillum's sweet spot was his natural ability to connect with the young people. He became an unflagging force in pushing through a new city center for teenagers, often stopping in unannounced to check on middle and high school students, even though most weren't old enough to vote for him.

"One thing about Andrew is that he's been consistent. Sometimes young people lose focus or they lose interest. He's never lost interest. He's always been consistent with his time and his talents," says Kendrick Meek, a former Democratic congressman from Florida.

It's around this point when he also became the national director of the Young Elected Officials Network, a project of the People for American Way foundation that created candidate training and a national pipeline to help young people succeed in campaigns and public office. Rep. Kyrsten Sinema, the 42-year-old Democratic nominee for U.S. Senate in Arizona this year, was also a participant.

The enthusiasm Gillum brought to his work there resonated so far up the Democratic leadership chain that House Speaker Nancy Pelosi invited Gillum to be her guest at Obama's 2009 inauguration.

***



After a decade on the city commission, an impatient Gillum made a bit of an audacious move for the mayorship of Tallahassee before Marks, the incumbent, had formally announced he would not run for another term.

"If he didn't create the mold he definitely helped establish stepping into leadership without waiting for anyone to give you permission," says Angela Rye, a Democratic political consultant and CNN political commentator who has tracked Gillum's rise.

Marks says he was surprised by Gillum's step at the time, but in hindsight says a 2014 campaign for mayor made sense if he was plotting further down the road.

"It did not occur to me then that he had a plan to run for governor. In retrospect, I think that may have been his plan, and he knew the timing," he says.

With Marks out of the way, Gillum coasted to an overwhelming victory in the campaign, earning 76 percent of the vote against two opponents. As mayor, he promised to be a "consensus builder" that would work to bring different parts of the community together. But he was also already eyeing his next step, briefly considering a congressional bid before passing on it.

It was November 2016, in the aftermath of Trump's jolting victory, when Gillum's next door nudged open. A group of college students circulated an online petition seeking to goad him into a run for governor. He responded with a Facebook post signaling his openness. But it was seen as merely a trial balloon, not a serious undertaking.

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The first Tampa Bay Times poll of insiders poured cold water on his prospects. In February 2017, 36 percent predicted wealthy attorney John Morgan would be the Democratic Party's strongest candidate for governor, followed by 33 percent for Gwen Graham, the former congresswoman and daughter of Bob Graham, the popular former governor and senator. Gillum was in last with just five percent. After all, the last Tallahassee resident elected governor left office in 1961.

Yet again, Gillum decided he wasn't going to settle for what the establishment was telling him.

In a conference call indicating his decision to enter the race, he acknowledged naivete about what might loom around the bend, but was also driven by being dismissed. "I am jazzed up," he said.

From the start, Gillum ran as himself, an undaunted liberal unwilling to dilute his values to win an election. He called for a corporate tax hike to generate $1 billion annually for school infrastructure and higher teacher pay. For even more revenue, he proposed legalizing recreational marijuana and taxing it. He confronted the National Rifle Association head-on, highlighting a city ordinance that prohibits people from shooting guns in parks. He advocated for restoring voting rights for felons. He boasted he was the only candidate running who believed in Medicare for all. He said Trump should be impeached.

Gillum would run as the black Bernie. It unnerved even some on his team.

The initial conventional assessment of this posture among the political class was that while it would gin up excitement among the base, it was doomed in a statewide primary or general election. Florida history instructed that Republicans would always nominate the most credibly conservative candidate while Democrats would choose the establishment favorite that hugged the center. (In Crist in 2014, they literally nominated a former Republican.)

But Gillum's advisers actually saw a model in Marco Rubio, who won a GOP primary for U.S. Senate in 2010 by galvanizing the ascending tea party. Gillum could do the same from the left by appealing to the hyper liberal, ultra activist resistance that was gelling across the country in response to Trump.

"If people saw him and heard him, he'd win," says Kevin Cate, one of Gillum's top strategists.

The initial poll after his announcement put him at 3.9 percent support among Democrats, in dead last place. Gillum struggled to raise money, becoming the last candidate in a field of five to air television commercials. But he determinedly worked the state, employing his natural charisma and social media skills to gradually build a following and snag bursts of attention.

He also was the beneficiary of a perfect storm of events. As Graham entered the homestretch as the front-runner, eccentric Palm Beach billionaire Jeff Greene made a curiously late entry into the contest and unloaded, by one estimate, more than $8 million, in attacks on Graham. At the same time, Greene cut into the south Florida base of Phil Levine, the wealthy mayor of Miami Beach.

Meanwhile, Gillum rallied with Bernie Sanders and was bolstered by a late infusion of cash from billionaire donors George Soros and Tom Steyer, who each donated $250,000 to his effort. Not having enough money to pay their original admaker Mark Putnam, Gillum's campaign cobbled together a spot one aide now describes as a "candy-coated liberal sugar high." Using clips of Gillum riffing on progressive sweet spots, Cate and his team laid synthesized ecclesiastical music that crescendos into the candidate's call to flip Florida blue in 2018 and the country blue in 2020.

They aired it predominantly in Miami's television market – "Broward County's the Holy Grail," says Cate – with the remaining funds devoted to television in Jacksonville.

All the while, Gillum's opponents largely ignored him.

"Nobody would touch him," says Steve Vancore, a Tallahassee-based Democratic consultant who was initially skeptical of Gillum's candidacy. In the final weeks of the primary, as he watched Gillum's crowds swell and burst with enthusiasm, Vancore believed that he would become the next big thing in Florida politics once this election was over.

"I did not know that thing would be the nomination for governor," he says. "Nobody saw this coming."

On primary night, Gillum won every county where black voters make up more than a quarter of registered Democrats, including the two largest of Miami-Dade and Broward, where he swamped Graham by a more than 2-to-1 margin. In a five way race, it was divide and conquer.

Despite a 10-to-1 spending disadvantage, he ended up capturing just over a third of the vote, defeating Graham by 3 points or about 45,000 votes. When the AP called the race for Gillum, a chant broke out at his party: "Do we believe in polls?," yelled a supporter. "No!" the crowd chanted.

"I always thought Graham was going to be the nominee," says Yordon. "I think Gwen would've been a very effective candidate. I'm now coming around. I'm seeing a side of Andrew and how he's dealing with success. It's a moment to be humble, and he has been. That's a very important thing. It's easy to have your chest out right now, but instead he's extending his hand."

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Andrew Gillum speaks to the media at a campaign rally on Sept. 24, 2018 in Miami. (Joe Raedle/Getty Images)

While Gillum's strategists continue to espouse confidence, Republicans are doing everything to leverage Gillum's most glaring vulnerability against him in the closing days in a state where the last two governor's races were decided by a mere 70,000 votes.

The most potent attack against Gillum has been the peculiar cloud of an FBI investigation into Tallahassee officials' dealings with developers. Gillum has repeatedly stressed the FBI has assured him he is not their focus, but it's placed him in political purgatory as the investigation continues without a clear indication of who is in their sights.

It's an unstated rule that the Department of Justice does not discuss or act on its investigations within two months of an election. But disclosures from an attorney to a lobbyist and former close confidante of Gillum have shown that Gillum apparently accepted multiple gifts, including tickets to the Broadway show "Hamilton" and catering for a political fundraiser, from an undercover FBI agent during the attempted sting. There's also a discrepancy over whether Gillum fully paid for a trip to a luxury resort in Costa Rica with the lobbyist and the agents.

"It doesn't look good and it's kind of amateurish for him to put himself in that situation," says Ben Wilcox, the research director of Integrity Florida, a nonprofit watchdog group.

Gillum has apologized for not asking more questions about the source of the "Hamilton" ticket, but otherwise maintains that he did nothing untoward, let alone illegal.

But it's the air of suspicion that confounds: Why would up to 20 FBI agents position themselves around him for years?

"They were just doing their job," Gillum says. "It's their job to root out corruption anywhere it exists. But if they were around to find me doing something wrong, good luck to them. If they were looking for me to have bait for them, they would be severely disappointed."

***



DeSantis' path to victory is to blow Gillum away among white voters, while betting that the long-promised surge among African-Americans and young people doesn't materialize in this off-year election. With the vote in the Panhandle expected to be down due to the aftermath of Hurricane Michael, DeSantis will also need to perform better in soft GOP counties around Tampa and Sarasota.

Gillum's roadmap is to be competitive in DeSantis' homebase of Jacksonville, dominate the Orlando area and then slaughter DeSantis in Miami-Dade and Broward counties, holding him to about a third of the vote.

And while both campaigns appear to be turning inward toward their respective bases in the closing days of the election, Democrats believe that for all the hypercharged rhetoric, the political construct of the statehouse in Tallahassee will rein Gillum in.

No matter what size of blue wave rolls up on to Florida's shores on Election Night, the next governor will be working with a Republican legislature.

On the stump in these final days, Gillum still promises "radical change," and his friendly audiences reply with the comfortable affirmation of cheers and nods.

But in the interview, the man who cut his teeth in politics by protesting power in the state capitol is showing some signs of bending to the guardrails of pragmatism.

"I consider myself an activist who governs," he says. "I'm extremely passionate about the issues we're advocating for, but I'm also passionate about delivering."

This student activist is beginning to sound more like a governor.

