Ask Andrew Gillum about when he caught the political bug, and it’s more likely than not the Tallahassee mayor will talk about his early days at Florida A&M University, when he led protests in the state Capitol just blocks away and was eventually elected student body president.
But the Democratic nominee for governor, who later served a decade on the city commission before being elected mayor, has long hinged his political identity on his humble roots far from the state’s capital city. How did Gillum, as the son of a school bus driver and construction worker growing up in Richmond Heights, end up in politics competing at the state’s highest level?
The answer lies 150 miles southeast of Tallahassee, in Gillum’s teenage years after his family moved to Gainesville. There, as one of only two African-American male students in his AP-level classes in high school, he met and befriended the son of a state legislator who — long before Gillum went to college — helped open some of Gillum’s first doors to Tallahassee politics.
“I hadn’t to that point known anybody so close to government,” Gillum said recently. “I definitely don’t think I would have been as receptive to the idea that it was accessible to me, because I hadn’t to that point known anybody so close to government.”
Gillum’s family moved to Gainesville in 1992, Gillum has said, to be closer to his ill grandfather.
Gillum, who turned 13 that summer, quickly stepped up at Westwood Middle School, where he pushed for more snacks in the vending machines as homeroom representative from 6th to 8th grade, he told the Gainesville Sun.
“At that time it seemed something major to have Skittles, Snickers and real Doritos, not generic taco chips, in the vending machines,” Gillum told the paper in 2003. “We got some diversity — Skittles and Snickers, but not the Doritos.”
But it wasn’t until he entered Gainesville High School in the fall of 1994 that he would meet and befriend Christopher Chestnut, the son of two local politicians. His mother, Rep. Cynthia Chestnut, had been a city commissioner and mayor before she became a state lawmaker in 1990, while his father, Charles Chestnut III, sat on the Alachua County Commission.
Andrew and Christopher eventually became best friends but were an odd pair in Gainesville, by Chestnut’s own admission.
“He was the teacher’s favorite — all the teachers loved him,” he said. Gillum — in penny loafers, khakis and his tucked-in button-down shirt — cut a serious silhouette at Gainesville High. Chestnut, on the other hand, “was like the teacher’s antagonist, so we had a love-hate relationship.”
Gillum and Chestnut also occasionally faced off in disciplinary teen court, where Gillum would serve as prosecutor and Chestnut, foreshadowing his later work as a lawyer, would play defense attorney. But both eventually bonded over being the only African-American boys in their AP classes and over a shared interest in student government.
Chestnut, however, had already grown up steeped in politics because of his family. Soon, Gillum would find himself immersed in it, too. They began working campaigns together as a hobby, helping with his mother’s re-election bids to return to Tallahassee or hanging around events held at the Chestnut home.
Gillum, who lived a 12-minute bike ride away, became a regular visitor.
“When you saw one you’d see the other,” said Cynthia Chestnut, who still lives in Gainesville. Whenever he came over, “he would pick my brain about getting into politics, what was important to keep in mind about getting into politics, what I thought about various issues.”
Cynthia Chestnut “was the first governmental official that I personally knew,” he said, recalling times he’d go over to the Chestnut house to talk politics even when Christopher wasn’t there.
Cynthia Chestnut also opened doors for her son and his best friend — literally. They came up on breaks to visit Tallahassee during the legislative session, where they saw state government up close.
“I chaired education so they met lots of people — it was good exposure for them,” Cynthia Chestnut recalled. She also shared office space with then Rep. Willie Logan, a briefly anointed Speaker-designate from Miami whom Gillum would later work for during Logan’s unsuccessful independent run for U.S. Senate.
Those early trips, Gillum said, were the first time he had ever been to the Capitol or to Tallahassee. Cynthia Chestnut “was the gateway for me,” he said. “She was the point of entry for me to politics — in a real way, not just the student government pep rallies, plan senior prom. … Short of her, I would not have had exposure to that.”
“I could see the influence of exposure to government” on Gillum, Christopher Chestnut recalled. “He was just absorbing all of it.”
Gillum eventually graduated as student body vice president his senior year of high school. He was also elected by the state Association of Student Councils as state parliamentarian, tasked with bringing student proposals from across the state to the governor, then Lawton Chiles. He would, through that job, brush shoulders with another future Florida politician, Rep. Carlos Curbelo, Chestnut recalled, “both all-stars at a statewide level in leadership.”
Gillum’s decision to attend Florida A&M, Cynthia Chestnut’s alma mater, firmly ensconced him in the state capital once so unfamiliar to him and cemented his political path. He interned on legislative committees and helped lead a sit-in in then-Gov. Jeb Bush’s office in the Capitol over his reversal of affirmative action policies before launching his career on the city commission.
But the impact of those early visits to the Capitol are visible still in his bid for the Florida governorship. The Chestnuts, collectively, donated thousands of dollars to his primary campaign. Christopher Chestnut has traveled the campaign trail with Gillum, though not in any official capacity, and has continued to volunteer into the general election, he said.
(Chestnut has tangled with the Florida Bar several times since he began practicing law — he pleaded guilty to a Bar violation in 2015 for failing to inform a client on a wrongful death claim and was publicly reprimanded, though the Bar dropped complaints that included improper solicitation of clients and making false statements in court. The lawyer, who used to practice law in Gainesville but moved his firm to Atlanta, also has two disciplinary actions against him still pending with the Florida Bar.)
Should Gillum win the governorship, Christopher Chestnut said, Gillum has the benefit of a front-row seat to the Legislature few have observed so early.
“The Capitol was tangible for him,” he said. “He’s been there before.”