An Insider in Florida Politics, Running for Office as an Outsider

TALLAHASSEE, Fla. — City Hall never did seem big enough for Andrew Gillum.

It was November 2014 — Gillum’s swearing-in as mayor of Tallahassee — and typical accommodations would not do. Traditionally, the city had inaugurated its new government quietly, in its municipal chambers. But Gillum, then 35, wanted a party. He wanted, colleagues groused, to be seen making a speech.

And seen he was.

“I won’t always get it right, but I’ll be honest,” Gillum said in an outdoor address, as a constellation of lobbyists, friends and lobbyist-friends at the city’s tailgate-style festival looked on — their faith and investment in him rewarded. “We’ve got some good times ahead, y’all.”

Four years and one long-shot campaign later, this has proved true for Gillum. With his upset victory in the Democratic primary for governor in August, Gillum, 39, has continued on a glide path to the party’s upper reaches that began about a mile down the road, as a student government leader at Florida A&M University, before he was old enough to drink. He may be elected the first black governor of the nation’s largest swing state in November, as his race against former Rep. Ron DeSantis, a Trump acolyte who just turned 40, emerges as a national proxy for the parties’ dueling futures.

Gillum’s admirers see in him a hybrid of Bernie Sanders and Barack Obama — an authentic progressive who supports higher corporate taxes and greater gun control, calls for the impeachment of President Donald Trump and Medicare-for-all, and can inspire young and minority voters in a state that last elected a Democratic governor in 1994. And in recent days, he has been ubiquitous, in his city and on television, as he managed the fallout from Hurricane Michael, at one point commandeering a chain saw himself to help clear tree debris.

Yet an examination of Gillum’s record lays bare the central contradiction of his political life: Self-styled as an activist-minded populist, with a lunch-pail upbringing in south Miami-Dade County, he is also an avatar of the capital city he runs — a town powered by ambition, horse-trading and alliances with well-placed power players.

One top campaign adviser — Sean Pittman, a close friend and mentor whom Gillum met as a student at Florida A&M — is also one of the city’s subcontracted lobbyists. Another senior strategist, Sharon Lettman-Hicks, also a confidante since college, paid the mayor a salary of $71,680 in 2017 to advise her boutique public-relations consulting firm, though he spent virtually all of his non-mayoral time running for governor. Until recently, Lettman-Hicks also served as the landlord of his campaign headquarters, collecting $38,087.50 in rent from March 2017 through August of this year, according to campaign finance records.

Gillum, in an interview, said he did not see these relationships or others with lobbyists as problematic. Rather, he has framed his own career arc as a triumph of within-the-system maneuvering, his approach summed up in a stock line to campaign audiences: “If you’re not at the table, you’re on the menu.”

In ensuring he has had a seat, for the better part of two decades now, Gillum has earned the label that most elected leaders strain to avoid: career politician. He won election to the Tallahassee city commission at age 23 and has never left public office. Though the job of mayor is largely ceremonial, representing one of five votes on the commission, Gillum has engendered fierce loyalty among working-class constituents for his emphasis on criminal justice and education for low-income students. He has also tended to relationships with a more affluent set, long before attracting progressive billionaires like Tom Steyer and George Soros to his cause.

“Does he have friends who are lobbyists? You bet,” said Allan Katz, a former city commissioner who served with Gillum and later became Obama’s ambassador to Portugal. “Did I have friends who were lobbyists? You bet.”

And as Gillum seeks the state’s highest post, at least one of those friends has brought baggage, dragging his name into an FBI investigation and, unbeknown to him, placing him in the extended company of undercover agents. About two years ago, a lobbyist, Adam Corey, who had been close with Gillum since their student government days, introduced him to men who identified themselves as out-of-town developers eager to invest in property on Tallahassee’s south side — but were in fact working undercover to investigate the city’s community redevelopment agency for possible corruption.

Gillum has insisted that investigators told him he is not their target, and the inquiry has yet to produce any indictments. But subpoenaed documents revealed that Gillum took two personal trips in 2016 with Corey: one to Costa Rica with a top Gillum adviser, Pittman, and another to New York with Gillum’s younger brother and the agents. Gillum has said he paid his own way for most of the travel, with his brother treating him to a Broadway performance of “Hamilton” and a hotel stay. Both trips are under investigation by Florida’s state ethics commission. Gillum’s younger brother, Marcus, declined to comment, and a lawyer for Corey declined to provide further case details.

Gillum’s defenders have said any whiff of impropriety is inconsistent with the man, and the city, they know.

“There is no corruption in the city of Tallahassee,” Curtis Richardson, the city’s mayor pro tempore, said in an interview. (Later, he seemed to hedge slightly: “It’s not like it’s systemic corruption, and multiple individuals are involved, and it’s from the top down. It’s not that at all.”)

Katz, the former commissioner, said Gillum had been too ambitious, for too long, to behave recklessly. “He always was looking for a political future for himself and was therefore, I think, extremely careful,” Katz said. “But all of us who’ve been involved in politics sometimes wind up in the wrong room with the wrong guy.”

Gillum has chafed most at the labels applied to him as the investigation churns, which he believes fail to capture the totality of the affair. “You only put people in characters: ‘lobbyist and mayor,'” the mayor said of the lobbyist matter during a 45-minute interview at a local coffee shop. “I have a very easy time saying no to friends.”

But Gillum has also blamed his entanglement in the investigation on a too-trusting disposition, presenting himself as a well-intended naïf despite a political antenna that friends describe as preternatural. That Corey or others thought they could lure him into trying to break the law is “offensive,” Gillum said. He asked why anyone believed he could be corrupted in the first place.

“What about me makes you think that it’s appropriate?” he said. “What is in the atmosphere that would suggest that I’m the right person?”

From an early age, Gillum had always been the serious one, politically minded enough to make C-Span his appointment viewing in middle school, warming to a California congresswoman, Maxine Waters, who he long assumed was his representative because she, too, was black.

At Gainesville High School, Gillum, the fifth of seven children of a bus driver and a construction worker, became vice president of the student body, standing out as one of two African-American boys in advanced placement classes.

The “principal” nickname owed to his hyper-diligence in his elected role. “When the teacher asked, ‘What are we doing at this meeting today?’ the others said, ‘Well, Andrew has the agenda,'” said Cynthia Moore Chestnut, a former state representative and the mother of Gillum’s best friend in high school.

Once at Florida A&M, Gillum quickly announced himself as a canny organizer, working on the Senate campaign of Willie Logan and sidling up to several mentors across the state’s black political establishment. In one early crusade, he helped introduce a “Mr. FAMU” competition to complement a popular “Miss FAMU” pageant for women. And working with two state legislators in 2000, Gillum orchestrated a student march on the governor’s office in response to then-Gov. Jeb Bush’s effort to turn back racial preferences in public university admissions.

“He was preparing himself then,” said one of the former legislators, Anthony C. Hill, then a state representative.

Peers seemed to agree. “Andrew Gillum is merely positioning himself for a future career as a Democrat politician,” a recent Florida A&M alumnus wrote to Bush in 2002, according to email archives released when Bush ran for president, urging him to speak at the school’s graduation over the protests of Gillum, the student body president. (Bush did not speak in the end.)

Before graduating, Gillum was already eyeing an open seat on Tallahassee’s city commission, believing he could galvanize a new bloc of student voters often disconnected from the civic arcana of the city itself. Some supporters were skeptical.

“I told him, ‘Andrew, you’re not from Tallahassee, you’re from Gainesville,'” Hill remembered. “He said, ‘Yeah, but I think I can get the students behind me.'”

Despite meager fundraising, he prevailed in a runoff election, moving immediately to expand his base of support. Another commissioner, Gil Ziffer, recalled an early speech from Gillum before a nearly all-white political club. He won the crowd by reciting advice he said his father had given him about the “five B’s” of public speaking, especially to white audiences: “Be brief, brother. Be brief.”

Gillum also kept a foothold outside of City Hall, working with other young elected officials nationally as a leader of People for the American Way, a liberal advocacy group. He developed a reputation for seeing around corners politically. Gillum was an early supporter of Obama, urging fellow commissioners to keep their powder dry in the 2008 contest against Hillary Clinton. Katz, who heeded Gillum’s advice, joined him in South Carolina on the state’s primary night, where they encountered the future president. “He knew Andrew right away,” Katz said. “Obama looked at him with a big smile and said, ‘Andrew, how’s my young commissioner doing?'”

When Clinton ran again, Gillum endeared himself to her team, too, becoming a top Florida surrogate and securing a place on a leaked list of about 40 potential running mates, as he has mentioned often during the campaign. But he did rebuff one request before the state’s 2016 primary, according to a former Clinton aide: to attack Sanders directly. The decision proved foresighted; Sanders’ endorsement helped elevate Gillum in his own primary for governor this year.

As mayor, Gillum’s tenure has been defined often by the less glamorous trials of local government. He has confronted devastating storms — Hurricane Hermine in 2016 and Hurricane Michael last week — that left thousands of residents without power, taking care recently to remain ever-visible in the recovery efforts and document his doings in social media posts and cable news appearances.

He has also faced criticism at times for crime in Tallahassee, the biggest city in Leon County, which has the highest crime rate in the state. There were 22 murders in the county last year. Colleagues say the perception is unfair to Gillum, who moved to hire dozens of new police officers as concern grew.

His platform for governor has been loftier: raise the corporate tax rate, significantly boost public school funding, legalize marijuana, repeal the “Stand Your Ground” self-defense law that has long been contentious in the state.

But much of his agenda would be dictated by the pliability of the legislature, which is likely to remain under Republican control, making many of his promises difficult to honor on his own.

“Clearly I live in the capital city, and there are a lot of lawyer-lobbyist people,” Gillum said in the interview. He argued that it was a mistake to conflate his city — a community of students, families and a striking number of mattress stores — with the political excesses of state government.

But his case is complicated by recent events. Gillum’s predecessor as mayor was investigated by the FBI but never charged. So was a recent school district superintendent, in a separate FBI inquiry, also without a charge.

The city does little to discourage the smoke-filled caricature of white-collar swampiness. At its main power lunch spot, Andrew’s (no relation), across from the Capitol, the sweet potato waffle fries are named for a city commissioner under investigation for an alleged pay-to-play scheme. The muses for the cheeseburger and key lime pie were recently found to be having an affair.

“There are no secrets in Tallahassee,” said Ed Narain, a former state representative.

But there is an FBI inquiry, and a mayor eager to protect his own name. Gillum supported posting online the city records subpoenaed by investigators. He shares liberally on Facebook, with direct-to-the-people messages about his work. He is raising three children with his wife, R. Jai, another A&M alum, in the city he oversees.

“There’s no difference between his public life and his private life,” his pastor, the Rev. Julius H. McAllister Jr., said. “It’s intertwined.”

At times, though, Gillum has stood accused of blurring lines that others assumed were clear.

His office spent about $5,000 in taxpayer dollars in 2016 to buy software from a Democratic Party vendor to send political emails, an improper purchase that Gillum defended until being forced last year to pay the city back and apologize.

He voted in 2013 to give Corey, his college friend-turned-lobbyist, over $2 million in public funds to redevelop an old power plant into a high-end restaurant, after a city attorney ruled that having the mayor vote on a contract for Corey, his former campaign treasurer, did not constitute a conflict of interest.

And Gillum signed off last month on extending a contract for the city’s legislative lobbyist, who retains Pittman, the top campaign adviser, as a subcontracted lobbyist. Gillum said Pittman had not spoken to him about the extension. Pittman also joined Gillum and Corey on the 2016 trip to Costa Rica that is now under state ethics investigation. (Pittman was an early investor in Corey’s restaurant.) Gillum — who earned $79,176 as mayor last year, in addition to his more than $71,000 in consulting income — has said he and his wife paid for their share of a $1,400-a-night villa in cash; as evidence to ethics investigators, he provided a bank statement showing a $400 withdrawal before their departure. (An attorney for Corey, who won the villa at a charity auction, said his client was not reimbursed.)

In an interview, Pittman said that he and the mayor were “no different from any other family friends who have been close for decades.”

“When you’re a public figure, there are people who look for reasons to negatively impact your success,” Pittman said, calling his bond with Gillum “a beautiful relationship and not one that I think either one of us would allow someone to try to cheapen.”

While residents have described a “cloud” accompanying authorities’ attention, Gillum’s campaign has proceeded apace, at least until Hurricane Michael, which prompted him to cancel political appearances for over a week. Polls show Gillum in a tight race with DeSantis, and his events have retained the hum of momentum from his surge late in the primary, with a sea of autograph-seekers shouting for “Andrew."

At a rally last month in Broward County, waylaid briefly by a sun shower, Gillum called off local organizers who had been fussing with a banner in the downpour. “We don’t need a banner,” he said, gesturing to the mob surrounding him beneath an overhang. “We got a banner right here.”

He had just one three-word directive through the elements: “Let’s win, y’all.”