A Revolt in The Villages Takes a Stunning Turn

A tale of fascist dystopia turns into one of grassroots revival

You might remember that back in February 2023, when Florida Gov. Ron DeSantis was surging in the presidential polls, I reported out a story of a wild case of corruption and abuse in The Villages, the iconic Florida retirement community, that went unexpectedly viral. 

Now I have the sheer delight to share a new update and it’s about as gratifying as anything I’ve gotten to put in print. If you didn’t read the first piece, here’s the chef’s recommendation for a delicious reading experience: Set aside 20-30 minutes to read the first one, but don’t start it until you have a little free time, because each section of it just gets wilder, and you won’t want to put it down. 

Then spend a few moments contemplating how you think the story might have unfolded over the past year and half. Then imagine what a best-case scenario might look like. Then come back to this newsletter, and I imagine you’ll be surprised how the story went – and how much of it is left to tell.

The outcome is also something readers of a proto-version of this newsletter can take some significant pride in. The original story was about a county commissioner who’d been jailed on a flimsy felony perjury charge after he took on the local machine. In the first article and in our podcast about the story, we included a link to his GoFundMe for legal ex penses. Readers ended up contributing tens of thousands of dollars to the fund, which enabled him to appeal his conviction—which then delivered the next chapter of this story. 

Now the latest on The Villages saga:

A Revolt In The Villages Has Taken A Stunning Turn

By Ryan Grim

In a dramatic reversal, a former county commissioner in The Villages has been freed from jail, officially exonerated, restored to his seat on the Sumter County Commission, and is now running for re-election in a competitive Republican primary scheduled for August 20. Florida Circuit Court Judge Anthony Tatti was ordered by a higher court in November 2023 to enter a “not guilty” verdict in the state’s case against Oren Miller. Tatti finally did so on January 11. In a fit of pique, he threw his glasses across the bench, and stormed out of the courtroom. Five days later, he resigned and returned to private practice. 

That outcome seemed absurdly implausible when the 72-year-old Oren Miller first stepped into the common room of the county jail that would be his home for 73 days in 2022. 

Miller was in jail following a felony perjury conviction, awaiting sentencing. Most nonviolent convicts – such as Donald J. Trump – are released on bond awaiting sentencing, yet Miller had been taken directly from the courtroom to jail. 

It was all a shock to Miller, who’d worked for 40 years at the Caterpillar plant in Joliet, Illinois, before retiring to The Villages, Florida. Miller’s entry into late-in-life political office was triggered by a major property tax increase to fund infrastructure upgrades that would largely benefit The Villages’s corporate entity, known locally as “the developer.” Here the interests of the residents and the developer diverged: Retirees saw no advantage in over-crowded happy hours, more golf-cart traffic, or harder-to-book tee times. They certainly didn’t want to pay for it themselves, given that so many retirees lived on fixed incomes. If the developer wanted more development, Miller believed, the developer should pay for it. 

Despite being massively outspent by the developer, Miller and two allies, who ran as a slate against the property tax increase, won their commission seats in a landslide. The developer fought back immediately, pushing legislation through Tallahassee that effectively banned the commission from rolling back the tax hike. The lead author, who represented Sumter County, was literally on the developer’s payroll, earning an income of $925,096 from The Villages in 2021.

The Republican state attorney for the Sumter Counter, Bill Gladson, meanwhile, opened a meritless Sunshine Law investigation into the commissioners, accusing them of violating open records requirements by discussing commission business outside of the commission. There was no real evidence for the charge, and the prosecutor never brought those charges, but instead charged Miller and his ally Gary Search with perjury in the course of their interviews with prosecutors. 

The perjury charge was absurd: Miller and Search denied improperly discussing commission business, but couldn’t exactly remember on which dates they had spoken and about what. When shown phone records, Miller said that whatever the phone records showed was correct. Search, himself in poor health as well, took a plea deal to avoid jail time. “I think I would have survived [being jailed], but my wife wouldn’t,” Search told me recently. The deal Search made was to agree not to run in the 2022 election and in exchange his record would be expunged.

Miller fought it and went to court, running up against Judge Tatti, who betrayed open hostility to Miller throughout the trial, repeatedly overruling Miller’s attorney’s repeated objections, rulings the appeals court later found erroneous.

Miller was found guilty. 

Florida Gov. Ron DeSantis, an ally of the developer, removed Search and Miller from their commission seats after the state attorney filed charges. Yet a GoFundMe set up for his legal defense raised more than $40,000, allowing him to hire an attorney to file an appeal. 

The appeal hearing was brutal for the prosecutor, who struggled to justify bringing the charges. Judge Harvey Jay, appointed to the bench by Republican Gov. Rick Scott and reappointed by DeSantis, picked up on the fact that Miller was charged with falsely saying his phone calls with Search stopped in January when in fact it was the prosecutor who first said that, and Miller simply agreed with him, while later saying he wasn’t sure and accepting whatever the records said.

Jay asked the prosecutor: “At the time he is asked, ‘You said January,’ he had not said January. Is that a big deal for us? I mean, it was just simply not the case.” 

“Police may lie,” the prosecutor responded, describing a scenario where an officer falsely tells a suspect that his friend has confessed, so he might as well confess too. Judge Adrian Sound, another DeSantis appointee, jumped in to note how wildly different the two scenarios are. 

He then drilled down on the prosecutor’s implicit claim, that an investigator can lie to a suspect, and if the suspect doesn’t correct them, they’re guilty of perjury, even if they’ve made different claims elsewhere in the interview. “Can a failure to correct—what you just described, he should have corrected … can the failure to correct then form in part or in whole a basis for perjury?” Sound asked. The absurdity of such a claim hung in the courtroom.

The not-guilty verdict also meant Gov. DeSantis was required to put Miller back on the commission and offer back pay. DeSantis dragged his feet for months. In January, Miller filed suit against DeSantis to force him to follow the law and give him his job back. Circuit Court Judge John Cooper ruled on April 4 that there was “prima facie ground for relief”—legal lingo for “this is obvious.” Cooper gave DeSantis a short window to make it happen, and in late May, DeSantis finally issued his reluctant order reinstating Miller to the commission, completing the first leg of his comeback. 

The statute also requires Miller to be given back pay for time missed on the commission, but it’s unclear who is supposed to pay. The county has argued that the state should pay, since DeSantis removed Miller from his seat, while the state argues it’s a county problem. Miller said his attorney believes they could win in court, but it would cost as much in legal fees as he could potentially recoup, which is some $160,000. Miller said he’s dropping that effort.

That leaves the matter of re-election. Miller is facing an opponent who has raised more than $90,000 from the developer and assorted allies. Miller said he has raised nothing. “I’ve raised absolutely zero,” he said. “I don’t wanna do mailers, don’t wanna do signs. I’m running on my reputation.”

Meanwhile, shenanigans continue. Sumter County is so thoroughly Republican that the winner of the primary always goes on to win the general election. Because no Democrat runs, both independents and Democrats are allowed to vote in the GOP primary. But there’s an exception to that rule: If anybody runs as a write-in candidate, then the general election is considered to be an active one, and only Republicans can vote in the primary.

The local Republican Party organized a slate of write-in candidates who are running for the express purpose of blocking Democrats and independents from voting in the August 20 GOP primary. We don’t have to guess that this was a strategy aimed at undermining Miller, because Samantha Scott, Sumter County Republican Party chair, spelled the strategy out in a letter to the editor of the Village News. Local critics of the strategy argue it’s illegal, because the candidates had to swear under oath they are genuinely seeking office, a claim contradicted by the county chair’s admission. Still, it’s hard to see the GOP prosecutor taking up the case. 

Search said that he thinks Miller has a decent shot of winning, and that people all around The Villages have urged Search to run alongside him. “I told Oren, ‘You’re a glutton for punishment.’ The Pennsylvania Dutch in me wants to say, ‘I’ll show you guys.’ But you get to a certain point and you say, ‘I don’t need this.’”

The primary election is on August 20.