TALLAHASSEE — Wearing plastic orange chaps over his blue slacks and a matching helmet, Andrew Gillum bent over a live oak felled onto a nearly empty street and sliced through branches with a chainsaw.
The mayor of Florida's capital had spent the previous 48 hours shoveling sandbags, monitoring the weather and bouncing from TV interview to TV interview as the most powerful hurricane ever to approach his city roared into North Florida. His run for governor officially on hiatus, here he was in the eerie atmosphere of post-hurricane Tallahassee hacking away at fallen branches while his chief of staff, an aide and a cameraman working for his campaign for governor looked on.
Gillum was hard at work. But was he governing or politicking?
"They're with me all the time, unfortunately," Gillum said about the campaign videographer as he wiped sweat from his brow. "I don't believe we'll put this on television."
Already nearing his third decade in Tallahassee's full-contact political arena, Gillum has lived a life on the trail. He was just a college sophomore when he led a student march on the Capitol, and hadn't yet earned his degree when he landed his first professional job with a national liberal advocacy organization. Not quite 40, he has spent his entire adult life strategizing and networking across the country — all while crafting policy and taking votes as a Tallahassee commissioner and mayor.
Previous coverage: Read more about Andrew Gillum's plans for Florida's economy, health care system and schools.
Gillum's breadth of experience has served him well in his run for governor, as he has an expansive social orbit that touches both coasts (of the country, not just Florida). Those assets helped him pull off a dramatic come-from-behind win in the Democratic primary, and have positioned him two weeks out from election day to possibly become Florida's first black governor.
But as he runs against Trump-endorsed former U.S. Rep. Ron DeSantis, the political roles Gillum has juggled for so long are colliding and creating one of the most dramatic campaigns in the country. And as he aims to make history, it's unclear whether the machine he built over the past 20 years will collapse under its own weight or propel him into the record books.
"He has a pretty good network," said Susan MacManus, a University of South Florida political science professor. "He early on knew where to go to raise crowds and how to get publicity for his visits. There are 400 cities in Florida, and it's paying off for him right now."
Gillum has continually toured the state since launching his campaign in March. He ends just about every appearance by snapping selfies with his supporters' cameras stretched from the ends of the long arms on his 6-foot-tall frame. Often in a weathered "G" ballcap, he answers tough questions with a smile, tells hecklers he'll be their governor, too, and gives a stump speech that revolves around the plight of the working class.

OCTAVIO JONES | TimesGubernatorial democratic candidate Andrew Gillum takes selfies with supporters after speaking to a packed music center during a town hall at St. Petersburg College in St. Petersburg, Florida on Friday, October 19, 2018.
OCTAVIO JONES | TimesGubernatorial democratic candidate Andrew Gillum takes selfies with supporters after speaking to a packed music center during a town hall at St. Petersburg College in St. Petersburg, Florida on Friday, October 19, 2018.

Gillum is the fifth of seven kids born to a bus driver and construction worker in south Miami-Dade, and the first in his family to graduate high school and college, so he has a bootstrap back-story to frame the most liberal agenda ever pushed by a Democratic nominee for governor of Florida.
"Some of the people in this race for governor believe we've got to run as Republican light in order to win Florida," Gillum said at an August primary rally with Sen. Bernie Sanders. "Our voters are going to stay home if they have to choose between someone pretending to be a Republican and someone who is a real Republican."
Read more: Bernie Sanders: Andrew Gillum can politically transform Florida
Gillum has been making a similar pitches for nearly 20 years. The big difference is there are more people listening now.
Back in 2000, when then-governor Jeb Bush was pushing to effectively end affirmative action in the state, Gillum was one of four students who led a massive march into the state Capitol rotunda in protest. Bush allowed four students, including Gillum, into his office to discuss the issue.
Even then, at 20, Gillum understood the value of a focused pitch and the power of numbers. And he had the gift of persuasion.
Read more: How Andrew Gillum's Miami childhood shaped the views of Florida's would-be governor
Read more: This Gainesville political dynasty introduced Andrew Gillum to politics
"Andrew could convince a river to part," says Melanie Roussell Newman, one of the students who met with Bush.
Gillum's gift of gab didn't sway Bush, who ultimately ignored the students' suggestions and moved forward with his unaltered One Florida proposal.
But Gillum didn't back down. He blasted the governor in the press for putting "spin" on their talks, leading Bush to declare, "I didn't think I was negotiating with anybody."
Bush's agenda passed. But Gillum wasn't done fighting. Exactly two years later, film producer Norman Lear's People for the American Way brought actor Alec Baldwin to headline a rally at a Tallahassee church. Gillum stole the show. Now the elected student body president, he swore to boycott the governor if Bush gave his customary speech during the FAMU graduation ceremony. (Bush bowed out, citing a scheduling conflict).
Sharon Lettman-Hicks, the head of Florida operations of People for the American Way Foundation, saw the speech and was impressed. She recruited Gillum to help build the organization's growing state operation.
His job was a natural fit. Gillum began touring the state registering voters for the 2002 elections. He and Lettman-Hicks came up with the "Arrive with 5" campaign to spread the vote in low-turnout minority communities.
"He started doing message campaigns around the coalition to reduce class size, felon re-enfranchisement work, registration efforts. Election protection was a big thing at that time. He was just so driven," she said. "'At some point,' I told him, 'I'll be working for you.'"
Working for an organization founded as a way to combat the conservative Moral Majority helped introduce Gillum to an expanding crowd of young, like-minded thinkers. He was already surrounded by an active network of FAMU student leaders, and his new connections — with Lettman-Hicks running his campaign — helped him shock Tallahassee in his first city commission race.
Gillum, who was so far ahead of his class in Miami that one of his teachers became convinced he was hyper-active, had a habit of out-pacing expectations. Even Mayo Woodward, a financial adviser who in 2003 was expected to replace former City Commissioner John Paul Bailey, was struck by how Gillum could draw a crowd.
"He was really, really good at getting people out to vote," said Woodward, who also remembers Gillum wearing the same suit to every campaign event. "You put him in front of a crowd, buddy, he could fire them up."
John Marks, who'd go on to be elected Tallahassee's first black mayor that year, now thinks Gillum's win was even more impressive than his own. He remembers a "surge" of late-breaking voters put Gillum over the top, not unlike the last-minute voting that helped Gillum go from third to first in the final days of the Democratic primary for governor.
"Remarkably, he's doing it the same way this time," Marks said. "He came from behind, and had this surge. He did it again. The parallels are there."
Among them: Gillum's ability to build and keep relationships, and tap into a network of volunteers, strategists and donors tied together by his job and previous exploits. When Gillum's campaign for governor was running short on cash in the Democratic gubernatorial primary this spring, he sought out billionaire donor George Soros while on a west coast trip. A month later, Gillum was on the phone with hedge-fund manager Tom Steyer, who reluctantly broke a rule against making primary endorsements and has since committed about $8 million in Gillum's support.
Read more: Andrew Gillum gets another $650,000 from billionaire donors Soros, Steyer
Steyer's blessing went beyond cash. He essentially turned his NextGen America's field operation into the foot soldiers for a candidate who not only had a gift for public speaking but also a background in political operations and policy.
"Andrew Gillum is a campaign strategist," said Lettman-Hicks. "He is deeply steeped in the concerns of everyday people and how to make government work better for the people. He is a student of public policy."
Marks, the former mayor, was impressed with the young commissioner during his early years on the dais. He believed that his understudy would move beyond city politics when he announced his bid for mayor in 2013, but wasn't sure where he'd land.
"I did see Andrew moving on to higher political positions, yes. Governor? I don't know," he said. "In retrospect, when you think about it, when he ran for mayor, that was probably on his mind: 'I'm going to use this as a stepping stone for another position.'"
By the time Gillum became the city's figure-head mayor, he was well-connected and entrenched in Tallahassee politics. His marriage in 2009 to R. Jai Howard, a fellow FAMU grad with whom he has three children, further expanded his circle. Congressman Alcee Hastings' daughter, for instance, was Howard's sorority sister, and at the time of their marriage she worked for then-chief financial officer Alex Sink, who went on to run for governor.

TALLAHASSEE, FLA. 8/28/18-Andrew Gillum, one of the Democratic candidates for governor, right, carries his son Davis, age 14 months, as they walk into the polling place with wife R. Jai, second from left, son Jackson and daughter Caroline, both four, to vote Tuesday morning in Tallahassee.
TALLAHASSEE, FLA. 8/28/18-Andrew Gillum, one of the Democratic candidates for governor, right, carries his son Davis, age 14 months, as they walk into the polling place with wife R. Jai, second from left, son Jackson and daughter Caroline, both four, to vote Tuesday morning in Tallahassee.

But the many relationships that served Gillum so well as he climbed the ladder have also become one of his biggest weaknesses as the campaign for governor nears its end. Outside of speciously casting Gillum's economic policies as "socialist," DeSantis and the Republican Party of Florida have sought to drag the affable nominee down by tying him to some of his associates.
Gillum was criticized when, during the campaign, he voted to extend a contract for lobbyist Ron Book, who'd subcontracted work to Gillum campaign adviser and Tallahassee power broker Sean Pittman. And Gillum paid more than $30,000 in rent for his campaign headquarters to senior campaign adviser Lettman-Hicks before moving his headquarters in September. Lettman-Hicks herself paid Gillum $71,000 as a consultant to her small public relations firm last year after he left his $130,000-a-year job at People for the American Way when he announced his run for governor. She said Gillum, who is paid about $79,000 in his job as mayor, went on hiatus when he began his campaign.
When the Tallahassee Democrat reported last year that the FBI had planted undercover agents in Tallahassee to investigate dealings involving the city's community redevelopment agency, Gillum was quick to say he was told by federal investigators that they are not looking at him. But his friends' business venture was named in a 2017 subpoena. Pittman and former volunteer campaign treasurer Adam Corey were investors in The Edison hotel, which received a $2.1 million grant from the Tallahassee Community Redevelopment Agency, with Gillum joining the city's other commissioners in support. Gillum that same year also voted to spend $1.3 million upgrading an old coal-powered generator building to be operated as a brewpub by a business involving Corey.
Read more: What Andrew Gillum's trip to New York City means in the FBI investigation
Read more: What we know — and don't know — about the FBI investigation hanging over Andrew Gillum's campaign
Federal authorities have filed no charges in the case.
Erwin Jackson, a Tallahassee business owner, filed several ethics complaints, one alleging that Gillum violated ethics laws by taking a discount trip with his wife to Costa Rica with Pittman and Corey, and has questioned whether Gillum improperly traveling with Corey and two business people to Manhattan.
Gillum has been adamant that he has done nothing wrong. He released receipts and bank statements and bank statements from those 2016 trips voluntarily last month, although they didn't answer every question about who paid what. They did show, however, the Gillum's trip to New York with Corey began with a stop in Chicago to meet with Soros' Open Society Foundation, which his campaign explained was done through Gillum's job with People for the American Way. That trip continued to Manhattan, where Gillum and Corey hung out with two businessmen now believed to have been undercover FBI agents.
A picture from the trip of Gillum and Corey in sunglasses on a boat touring the Statue of Liberty was obtained by Tallahassee's WCTV , and then turned into attack ads by the Republican Party of Florida and Republican Governors Association that label Gillum "corrupt." Gillum says he mistakenly put his trust in Corey, but is adamant that the jaunt was nothing more than an easy afternoon on a boat.

"Mike Miller", an undercover FBI agent, developer Adam Corey, and Tallahassee Mayor Andrew Gillum in New York City in 2016. [WCTV]
“Mike Miller”, an undercover FBI agent, developer Adam Corey, and Tallahassee Mayor Andrew Gillum in New York City in 2016. [WCTV]
“I really am deeply offended by folks ascribing other meaning to it,” Gillum told WCTV.
Always smiling and direct, Gillum has answered questions repeatedly on the campaign trail about the investigation, and says he encourages the scrutiny.
If he's frustrated by it, it doesn't show. But for Lettman-Hicks, and other people who've known Gillum for years and watched him grow, the questions about his character and associations are maddening.
Roussell Newman, one of the FAMU students who was Gillum when he met with Jeb Bush, says he's unflappable because the pressure of being the first in his family to graduate was "heavier than any political weight." She remembers listening to his 2016 speech at the Democratic National Convention and thinking "God, he's going to run the party." Lettman-Hicks, who is 11 years Gillum's senior, said she moved her family back to Tallahassee specifically to be a part of a campaign for someone in whom she believes.
Even Alec Baldwin is still around, having attended a fundraiser for Gillum in March. And Woodward, who lives in Alabama but occasionally bumps into Gillum, says they're chummy enough to say "hi."
"He's been in politics all his life, so he's good at it," said Woodward. "He knows how to play the game. I'm not knocking him. More power to him. Some people play it better than others."