Issue 57: The Greek Tragedy of Andrew Gillum

He was hailed as a rising star.

The Florida political world woke up to a major news story yesterday. Former Tallahassee Mayor, a former rising star in Democratic politics, and 2018 Gubernatorial nominee, was indicted for fraud and corruption. The indictment comes after years of speculation around Gillum’s ethics. The indictment, the result of a grand jury, shows that Gillum and his longtime associate, Sharon Lettman-Hicks, solicited political donations that were actually for personal use. The 20+ page indictment includes pay-to-play crimes as well. It is a damning piece of news.

In wake of this, lets take a look at how Andrew Gillum’s star rose - and then crashed down.

City Politics

Andrew Gillum burst onto the election scene in 2003. Before this, Gillum had been heavily involved in community work. He was student body president in middle and high school, and would become FAMU Student Body President. Gillum showed tremendous drive. He organized protests against Jeb Bush’s efforts to move Florida into a more conservative direction, and was pegged as a future leader by the Congressional Black Caucus foundation. Gillum was involved in many organizations that focused on get-out-the-vote efforts; something he’d utilize in future runs for office. When a seat on the Tallahassee city council opened up, Gillum jumped into the crowded race; despite still completing his time at FAMU. At the time, he was just 23.

Tallahassee elections are non-partisan and city-wide; with a runoff if no one gets 50% in the first round. Most observers expected former County Commissioner Bob Henderson and well-funded financial advisor Mayo Woodward to make the runoff. Gillum shocked the city when he surged into 2nd place, narrowly edging out Henderson.

Gillum’s success came from dominant margins in the southside community and around both the FAMU and FSU campus’. At this time, council elections took place in the spring - February and March. Students had the ability to vote, but were much less engaged in local politics. Gillum was the “student candidate” and his GOTV operation led to a surge in votes around the campuses. Gillum’s pledge to focus on southside, which was overwhelmingly black and often overlooked by the city establishment - resulting in a large amount of urban decay, resulted in overwhelmingly support in the community. Woodward, who was strongest with the Republican-leaning North suburbs, advanced as well. Henderson, part of the white Democratic establishment, was squeezed out.

The runoff against Woodward was good news for Gillum. While the race was non-partisan, Gillum was a well-known Democrat and Woodward was a Republican. This led to a consolidation of the Democratic vote for Gillum; who captivated the city with his wit and tenacity. Henderson and Parrish backed him in the runoff. Gillum benefitted from TV and mail funded by the state party; which was being helped by outgoing Tallahassee Mayor Scott Maddox. This was part of an overall FDP push to win local offices after the 2002 re-election of Jeb Bush.

Gillum would easily take the runoff.

In early 2004, Tallahassee voted to move city elections to match with state races. This would mean the first round would be held in the August primary of even years, while runoffs would be in the November general ballot. This was part of a growing movement to consolidate elections and save costs.

As a result of the change, Gillum’s seat was up again immediately in 2004, and then not up again till 2008. After his impressive 2003 win, no one of note saw value in challenging the man already pegged as a “rising star.” Gillum defeated underfunded opponents easily - taking 72%. Fellow commissioner Mark Mustian did not even get an opponent.

After his 2004 win, Gillum would face no challenger in 2008. As this time went on, Gillum began to grow his statewide profile. He was known in Democratic circles as a future statewide candidate. He was even floated to run for Florida Democratic Party Chair in 2010. He was known as an involved commissioner who pushed many projects for underprivileged youth and communities. However, Gillum was not a boat-rocker by any means. Gillum was an outsider in his election, and while he remained a young reformer, he was still part of the left-of-center establishment by the early 2010s.

In 2012, Gillum actually generated some opposition. However, all three of his opponents were underfunded and faced no real prospect at defeating the commissioner. There were already rumors swirling Gillum would run for Mayor in 2014.

In 2013, Gillum announced he was running for Mayor He did this before incumbent mayor John Marks could formally announce he was retiring. This irked Marks, who like Gillum, was a Democrat. This actually showed the first unflattering side of Gillum’s ambition. Everyone expected Marks, who had some ethics questions and barely got re-election in 2010, to retire. Gillum did not wait, likely eager to avoid real opposition having a chance to jump the gun. The biggest likely threat to Gillum was former Mayor and then-commissioner Scott Maddox; who NOW sits in a jail cell for corruption! Read the saga of Scott Maddox here.

Maddox did not run, seeing that Gillum was too popular. No real opposition to Gillum emerged, and he won the Mayoral election in a total sleeper.

Looking Beyond Tallahassee

After his election as Mayor, Gillum clearly had his eyes on higher office. In late 2015, court-ordered redistricting let to a shift in the Congressional maps. The new 5th district, which united the black communities from Tallahassee to Jacksonville, was a good prospect for Andrew. However, before he could make a play for the seat, former State Senator Al Lawson jumped into the race. With Tallahassee-based Lawson and Jacksonville-based Corrine Brown both in already, Gillum entering would only serve to split the Tallahassee vote. In the end, Lawson would defeat Brown. Read more on that in my Lawson electoral history article.

Gillum also had his eyes on Washington DC via non-elected methods. Gillum came out for Hillary Clinton in the 2016 Democratic primaries. He campaigned for Clinton in South Carolina, a pivotal state for Clinton in stalling some of Bernie Sanders’ momentum. The speculation was Gillum would aim for an administrative post.

Well, we all know that didn’t happen.

Run for Governor

The election of Donald Trump gave Democrats an excellent shot at flipping the Florida Governor’s post. Traditional midterms hurt the party in power, and Trump proved to be an unpopular leader. The top Democratic recruit was former Congresswoman Gwen Graham; who’d flipped the Florida 2nd district in 2014, despite it backing Republicans at the top of the ticket. Graham’s district had been blown up in redistricting.

Many Tallahassee observers were shocked when Gillum entered the race for Governor. On top of that, his persona on the trail was different from the commissioner-turned-mayor. Gillum ran decidedly to the left of the rest of the field; courting the Sanders wing of the party. This was in contrast to his backing of Clinton and the fact that by this point he was very much part of the Democratic establishment.

Gillum’s campaign struggled for much of the primary, generating bad headlines for a string of ethical issues. His campaign started off with a flub when it was clear the city had paid for campaign software. In addition, the brewing investigation into corruption in Tallahassee, which as of this writing had led to three people going to jail, was roping in Gillum. Andrew had long been friends with a man named Adam Corey, who has long been perceived as a corrupt developer and wannabe king-maker. (If you read the indictment - its pretty clear Individual A is Corey). These brewing issue arose during the primary, and anyone who knows me knows that I was SCREAMING that nominating him would be a mistake.

Gillum got big help in the closing months of the primary campaign. He continued to trail in the polls, but he had outside help from left-wing orgs and donors. Just before the primary, for example, Tom Steyer and George Soros put over $600,000 into Gillum’s campaign. Gillum’s operation began to generate free media by claiming they were surging in the polls. This coincided with GOTV operations from third-party groups to boost Gillum. While he trailed in polls, he did start to rise, surging into 2nd right before the primary; with St Pete Polls the only org to catch his momentum. One thing aiding Gillum was his consolidation of the black vote, which until then he’d not unified.

On the opponent front, Gwen Graham was the frontrunner, but she’d been subject to attacks from self-funder Jeff Greene, who was collapsing in the polls. Miami Beach Mayor Phil Levine had a strong base in South Florida, but was not generating momentum elsewhere. His presence, however, prevented Graham from making real inroads in the vote-rich Southeast.

Heading into primary day, my personal gut said it would be close between Gillum and Graham. In the end, Gillum narrowly won the primary.

Gillum’s win was a major shock to much of the political class. He’d threaded the needle; surging just at the right moment. In addition, Gillum consolidated the black vote, which is a 3rd of the primary, winning heavily black precincts with 60% to 70% or more.

Gillum’s win was fueled by dominant margins in Dem-heavy districts. Breaking down the results by the our new State House districts highlights this. The map below shows Gillum utterly dominating in the black-majority and black-plurality house seats. Levine was strongest with white and Hispanic districts in South Florida. Graham won more district, but often with much more modest margins. She was strongest in rural, working class, and suburban seats. Gillum did well with white liberals, but he did not unify that block like he did with black voters.

How the primary broke down in Leon County, the home of both Gillum and Graham, is very interesting. Gillum won the county, fueled by strong margins in the African-American community and around the FSU and FAMU campuses. Graham was strongest in the suburbs, but also in the rural counties. Notable white liberal communities in Tallahassee: namely Indianhead and Meyers Park, narrowly backed Graham; with Gillum right behind.

Gillum would go on to face Ron DeSantis in the general. DeSantis had won his primary thanks to the backing of Donald Trump. DeSantis nearly nuked his entire campaign early into the general. He quipped that Florida couldn’t “monkey this up” in reference to Andrew winning the post. Gee… wonder what that means.

While the Gillum campaign got outside help from the national party, DeSantis’ operation was a mess for over a month. It was only in late September that national GOP forces installed Susie Wiles into DeSantis orbit to “right the ship.” Meanwhile, Gillum was hurt by late-breaking allegations around his ethics. Feeling the pressure of the investigations, which were now revealed to include undercover FBI agents, Gillum had thrown Corey under the bus; distancing himself from his friend. Corey repaid Andrew by leaking information. The infamous trip to NYC, including Hamilton tickets, all being paid for by an FBI agent posing as a developer, hurt Gillum in the eyes of the public when the story broke.

In the end, despite polls showing Gillum with a multi-point lead, DeSantis narrowly edged out a win.

The race was so close that a recount was needed. In the end, DeSantis took the race by 32,000 votes.

Aftermath

Before the election had even taken place, the prospect of Gillum running for President was already floated. Even with his loss, the rumors did not die down - specifically from the Gillum side! Gillum announced he would focus on voter registration in Florida, pledging to register 100,000 new people. This came as anger emerged that he had left over THREE MILLION DOLLARS in the campaign bank. It was hard not to imagine that money could have made the difference. Why had he held it? The likeliest answer was a war chest for that Presidential run.

Gillum’s 2019 was a disaster. He waffled around on the voter registration push, with it clear he’d never meet his goal. He spent much of his time traveling to do media interviews. Then, in early 2020, the infamous hotel room scandal emerged, and Gillum stepped out of the public eye.

Now, with a massive indictment, and jail time likely, Gillum’s star has truly fallen. He emerged on the scene with no much promise. His collapse feels like a Greek tragedy. Where did it go wrong? When was he corrupted? His fate is similar to that of Scott Maddox - who was elected to the council young - failed at statewide office - and now sits in a jail cell for corruption.

This all comes as Tallahassee prepares for a serious of nasty council races; which are pitting a surging left-wing voice against the developer-backed establishment. I’ll cover those races down the line.

In the meantime, we will see how things emerge with Andrew. My advice Mr Mayor, just take a plea. I read the indictment. You are screwed.