Oliver Gilbert beats back $2 million+ attack, wins crowded CD 24 primary

Oliver Gilbert beats back $2 million+ attack, wins crowded CD 24 primary
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They came at Oliver Gilbert with money. Lots and lots of money.

They came at him with attack ads, a crypto-funded super PAC, questions about his campaign contributions, Kendrick Meek Jr.‘s famous political surname and, toward the end, polls suggesting former State Sen. Shevrin Jones might beat him.

And Gilbert won anyway.

Not by much. The former Miami Gardens mayor and former Miami-Dade commissioner won Tuesday’s seven-way Democratic primary for Congressional District 24, where longtime Congresswoman Frederica Wilson just retired, with about 34% of the vote, edging out Jones by roughly two percentage points.

The state senator had every reason to think he could pull this off. Some late polling showed Jones comfortably ahead. He had built a legitimate base of support, had legislative experience and was running in a district where he was hardly an unknown quantity.

Read related: Florida Sen. Shevrin Jones won’t run for re-election; will he run for Congress?

But there was one small problem. Actually, there were several. And one of them was named Kendrick Meek Jr.

Welcome to the joys of a seven-way primary.

Gilbert didn’t need 50% plus one Tuesday. He didn’t even need 40%. He just needed more votes than everybody else.

And he got them.

Which means that, barring some political earthquake between now and Nov. 3, Gilbert is basically the congressman-elect.

Yes, Republican Te Mayonna Brown is on the November ballot and voters will make the final decision. But let’s not pretend CD 24 suddenly became a swing district overnight. This seat has been a Democratic stronghold since it was created in 1992 to give Black voters the opportunity to elect a representative of their choice. A Republican winning it would be the kind of upset that makes national news.

Gilbert may be arrogant AF and act like he knows better than anyone else in the room, but he’s not so bad that a Republican would win.

So Gilbert’s real election was Tuesday. And it was a hell of an election. Because outside groups spent enormous sums trying to make sure the next congressman was anybody but Oliver.

The biggest player was Protect Progress, the cryptocurrency-industry super PAC tied to the Fairshake network, which dumped more than $2 million into opposing Gilbert.

Think about that for a second.

More than $2 million in outside money spent trying to defeat a candidate in a Democratic primary for a congressional district stretching across predominantly Black communities in Miami-Dade and Broward.

Read related: Frederica Wilson drops the mic = North Miami-Dade’s musical chairs begins

Gilbert certainly noticed.

“This isn’t about me right now. This is about us,” he told supporters at his victory party at Topgolf in Miami Gardens. “This is about whether we will decide who actually makes decisions for us, not people in Washington who have a lot of money.”

Well, he’s never been subtle.

The crypto PAC’s involvement became particularly controversial after reports that attack advertising used what appeared to be fabricated Miami Herald headlines. Protect Progress maintained that the underlying allegations in its ads were accurate. But if you’re spending millions trying to persuade voters and the story becomes whether your newspaper headlines are real, something has gone sideways.

“You’d be hard pressed to find any Democratic primary in Miami Dade where more money was spent against a single individual candidate,” said Michael Worley, a campaign consultant who worked with the Gilbert effort.

“It showcases the incredible strength of Oliver Gilbert as a candidate, as a leader in the community and as someone who really connected with the voters,” said Worley, a prolific Democratic operative who has become something of a South Florida political Swiss Army knife — mail, digital, advertising, strategy, PACs, you name it — and whose client list reads like the seating chart at a Miami-Dade Democratic fundraiser.

Turnout was going to be low and Gilbert’s campaign concentrated on micro-targeting with digital ads that showed what he had already delivered to his community and connecting with the diehard voters — older African-American women.

“His years of deliverables for that community, and they’ve been considerable, were remembered.”

Gilbert had attacks coming from closer to home, too.

Meek repeatedly hammered him over contributions from CDR Maguire, the government contractor associated with the controversial immigrant detention facility dubbed “Alligator Alcatraz,” to Gilbert’s political committee, Common Voices.

Gilbert returned fire, accusing Meek of using his father’s Washington connections to help fuel attacks against him.

Ah, familia.

But Meek’s candidacy may have had an impact that went well beyond the attacks. He brought one of the most revered political names in this district into the race. His grandmother was Carrie Meek, the legendary former congresswoman who first won the seat in 1992. His father, Kendrick Meek, succeeded her in Congress and held it until 2011, when he left to run for U.S. Senate.

Then came Frederica Wilson.

So voters were effectively choosing among Gilbert, Jones and a member of the family that helped create the political lineage of the seat in the first place — plus four other candidates, which include other known entities like former county Commissioner Jean Monestime.

Read related: The race for Frederica Wilson’s throne gets crowded, will test political alliances

That’s a lot of vote splitting. And it may have hurt Jones at precisely the moment he needed consolidation. Jones finished close enough — about two points behind Gilbert — that he has every reason to wonder what this race would have looked like with fewer names on the ballot.

He conceded graciously. “This campaign was never about me or any one person — it was about the future we want to build together, and that fight doesn’t end tonight,” Jones said.

On Tuesday night, he issued a statement.

“Tonight, I called Commissioner Oliver Gilbert to congratulate him on a hard-fought victory. They ran a strong campaign, and I wish him and their family well.

“I want to thank every volunteer who knocked on doors in the South Florida summer heat, every supporter who chipped in what they could, and every voter who cast a ballot in this election. Throughout this journey, we had thousands of conversations on porches and at kitchen tables, and I am so grateful for those who shared their concerns, ideas, and vision for our community. This campaign was never about me or any one person – it was about the future we want to build together, and that fight doesn’t end tonight.

“Looking ahead to November, I’m committed to doing everything I can to help elect Democrats up and down the ticket. The stakes are too high to sit on the sidelines, and I’ll be out there campaigning and organizing for our candidates because our shared values are worth fighting for, in this race and every one that follows.

“To my family, my team, and this community that raised me and that I love – thank you for everything. This isn’t goodbye to public service; it’s a new chapter in the same fight for a Florida that families can actually afford. Let’s get to work.”

Gilbert also had something nobody else in the race could quite replicate: Frederica Wilson herself. She endorsed him early, and hung out with him, essentially signaling whom she wanted to inherit the seat she has held since 2011.

Read related: Frederica Wilson passes the torch to Oliver Gilbert in CD24 replacement race

Wilson arrived at Gilbert’s victory party Tuesday after his speech and provided perhaps the funniest endorsement of the entire campaign. She acknowledged that people sometimes complain Gilbert is arrogant.

“Well, all of the congresspeople are arrogant,” Wilson told reporters.

Thank you, Congresswoman. Ladra couldn’t possibly improve on that.

Wilson’s point, however, was that Gilbert has the stamina to continue the work she’s started and fight for the district. Those who distrust him say he’ll be fighting for special interests as he has for the Miami Dolphins, Hard Rock Stadium and Formula 1 racing.

Miami-Dade Mayor Daniella Levine Cava, another early Gilbert supporter, gushed at his victory, saying he had essentially been preparing for the job his entire political career. And, politically speaking, she has a point about the résumé.

Gilbert’s rise began in Miami Gardens, where he was appointed to the City Council in 2008 and elected mayor in 2012. He served two terms and became closely identified with the city’s economic development before winning a seat on the Miami-Dade Commission in 2020.

He eventually became commission chairman.

And then, when Wilson announced her retirement, nobody exactly fell out of their chair when Oliver decided Washington sounded nice. This has looked like the next rung on the ladder for a while.

Gilbert left the County Commission to make the run, so Tuesday wasn’t about whether he’d keep one political job or take another. He’ll be replaced by former Miami-Dade School Board Member Steve Gallon III, who was the only candidate to qualify and, as such, had already won.

Still. He pushed all the chips onto the table. And won.

Read related: Water wars: Oliver Gilbert pits Miami Gardens vs. North Miami Beach

There’s one thing  that tempers this victory — and that’s how little 34% looks like a mandate. Because it isn’t. It’s a plurality produced by a crowded primary.

The reality is that roughly two-thirds of Democratic voters chose somebody else. That gives Gilbert some political homework.

If he’s going to become the next representative of CD 24, he now has to bring together the Jones voters, the Meek voters, the Monestime voters and everybody else who spent the primary thinking Oliver Gilbert was not their guy. And is he too arrogant and vindictive to do that?

The district itself carries more historical weight than most.

It traces its roots to the 1992 redistricting that resulted in Florida electing its first Black members of Congress since Reconstruction: Carrie Meek in Miami-Dade, Alcee Hastings in Broward and Corrine Brown in Jacksonville.

Three decades later, the district remains heavily Black and Latino, with a substantial immigrant population, and it was altered again during this year’s congressional redistricting.

Gilbert wasted no time Tuesday moving from campaign warfare to congressional themes: affordable housing, healthcare, economic opportunity and education.

“We might speak different languages. We might come from different countries,” he told supporters. “But in the real world, we’re the same thing.”

Very congressional.

So, in short: Seven Democrats ran. Millions were spent. Outside interests tried to stop him. Shevrin Jones almost caught him. Kendrick Meek Jr. threw one hell of a wrench into the machinery.

But Oliver Gilbert is going to Washington anyway.

This kind of independent, government watchdog reporting is crucial to transparency and democracy. And more so every day. Help shine a light on the darker corners of our community with a contribution to Political Cortadito. Click here. Ladra thanks you for your support.

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