Meet Daniel Uhlfelder, Ron DeSantis' "Chief Tormentor"

Miami native Daniel Uhlfelder is determined to torment Ron DeSantis and get inside the "seriously sick" Florida governor's head.
Miami native Daniel Uhlfelder is determined to torment Ron DeSantis and get inside the "seriously sick" Florida governor's head. Daniel Uhlfelder photo
Standing outside a small airport in the Florida Panhandle on Monday night, attorney and activist Daniel Uhlfelder was approached by a deputy who shined a spotlight in his direction and asked with a southern drawl what he was doing there.

"I'm here because it's my understanding that this has been used as an airport to transport immigrants," Uhlfelder explained to the deputy. "The other day Governor DeSantis moved people through this airport."

Uhlfelder, who bills himself to his 255,000 Twitter followers as "chief tormentor of Ron DeSantis," was again on the trail of the governor. A Miami native who now lives near Seaside, he first gained national fame back in 2020 when he dressed as the Grim Reaper and roamed Florida's beaches to protest DeSantis' COVID-19 policies.

The stunt went viral and was featured on Saturday Night Live, The Daily Show With Trevor Noah, and on countless national news outlets. He followed that by starting a PAC called Remove Ron and ran for Florida attorney general.

Uhlfelder says that after losing to Aramis Ayala in the 2022 Democratic primary, he'd planned to take a much-needed respite from trolling the governor. But then came news of what he deems a "kidnapping operation": 48 migrants, most of them refugees from Venezuela, flown in two planes from San Antonio to Martha's Vineyard, where they were left stranded as pawns in a political stunt.

"It's like the Godfather movie: 'Just when I think I'm out, they pull me back in,'" says Uhlfelder, who's married with two young children. "If Ron DeSantis wasn't running this little kidnapping operation in my backyard, maybe I could have had a little break."

Before arriving in Martha's Vineyard, the planes from San Antonio landed for a brief time at Bob Sikes Airport in Crestview, Florida, not far from Uhlfelder's home in Santa Rosa Beach. And the company the DeSantis administration hired to transport the migrants, Vertol Systems Company Inc., operates out of nearby Destin. (Records show that the Florida Department of Transportation has paid Vertol nearly $1.6 million to relocate "unauthorized aliens.")

Leveraging his hefty Twitter following, Uhlfelder publicly asked for help in tracking the governor's moves. On Monday he received a tip that another plane out of San Antonio with immigrants aboard would be landing at the Sikes airport, which led to his encounter with the deputy. That night a plane from San Antonio landed at the time his tipster said it would and took off ten minutes later. He still suspects the plane had immigrants on it but can't be sure.

On Tuesday it was learned that one of the state-commissioned planes used in the Martha's Vineyard stunt was again flying out of San Antonio, stopping over for a brief time at the Sikes airport and then landing in Biden's home state of Delaware.

Suspecting it was carrying migrants, Uhlfelder tweeted out the information. Numerous national journalists staked out the airport in Delaware, but the plane wound up landing in New Jersey with no immigrants on board.
An administration source crowed to NBC News that DeSantis had "punked" the media. But the Miami Herald subsequently reported that a group of migrants in San Antonio had indeed been promised new lives in Delaware but were left stranded amid the media scrutiny.

In the midst of the chaos, the governor's administration took the opportunity to publicly insult Uhlfelder. "Regime 'journalists' fall for disinformation from a guy on Twitter who's famous for wearing a Grim Reaper costume to creep on beachgoers," tweeted Christina Pushaw, DeSantis' polarizing spokeswoman.

The tweet only confirmed to Uhlfelder that his work was having an impact: Pushaw wouldn't bother insulting someone who didn't matter.

So who is this middle-aged fellow who has drilled into the collective head of the DeSantis administration? To learn more, we got together with Uhlfelder for the following Q&A, which has been edited for length and clarity.

New Times: Have you always been politically involved?
Daniel Uhlfelder: I grew up in Tallahassee and my parents were always active. My dad's Steve Uhlfelder; he was a lawyer and lobbyist. He was chairman of the Florida Board of Regents. He was president of the student body of the University of Florida during Kent State and he was always very active. I was raised around people like [former Florida governors] LeRoy Collins, Bob Graham, Lawton Chiles; my dad worked for Reubin Askew.

But it kind of goes back a little farther. People ask me why I do all this stuff and I think a lot of it goes back to my great grandparents, who were killed in the Holocaust. They had some foresight and they were able to get my grandfather out of Nazi Germany as a young man in 1934. He came to West Palm Beach and was the first Jewish city commissioner in West Palm Beach. He was very active and he sat at the lunch counters at Woolworths when they were trying to integrate them in Palm Beach County. That's why I'm doing it. I owe it to my grandfather, to Governor Chiles, to LeRoy Collins, to my family to stand up to DeSantis, because it's just so wrong what he does on a daily basis.

What label do you put on yourself politically?
I was a Democrat growing up, I was a Republican for a long period of time, I'm a Democrat right now. I'm just a Floridian who cares about people being safe, and democracy, and about accountability. I would say I'm a moderate, in line with Lawton Chiles, Bill Clinton β€” a pragmatic moderate.

Do you get harassed up there because of your political actions?
I get harassed all the time. I have a quarter-million Twitter followers. You don't want to read the emails I get. [Laughs] I get plenty of harassment all over the place. Maybe not here locally, I've been here 20 years. Most of the harassment is trolls, you know.

When I tried to take down the Confederate flag, I did get harassed a lot locally on that. We have a Confederate flag at our [Walton County] courthouse that I've been trying to take down for 20 years. In 2015 we pushed it pretty hard, we had a petition, we had a website, we had a whole movement to bring the Confederate flag down. And it got pretty intense then locally. People showed up at my office and made threats against me and my family, so we had to have security at my house and office. What I learned at that point was the level of bigotry and the level of adoration toward the Confederate flag.

Around that time Trump started to come into play. I said, "Donald Trump will be president of the United States." People thought I was crazy. People said, "Why is that?" I said, "My experience with the Confederate flag."

I did not realize the underbelly of strong support and opinion for that. It was a cultlike level of adoration for this flag and what it stood for. What I have basically determined through all this, through the flag, through Trump, through DeSantis, is that there is a very strong and undeniable aversion and degree of hate and degree of mistrust of nonwhite people. And what Donald Trump and DeSantis are masters at is using that for their own power and benefit. That's what this is all about. That's why DeSantis is, in my opinion, one of the most dangerous people walking the Earth right now.

Before you put on the Grim Reaper outfit and strolled through the spring break crowd in 2020, how many Twitter followers did you have?
I didn't use social media until a few years ago, and then [former Arkansas governor] Mike Huckabee filed a bar complaint against me in 2019. I had 400 Twitter followers at that point. And then I publicized it and it went to 100,000 followers that weekend. It just went crazy. Huckabee tried to privatize our beaches and I fought him on that. I was involved in starting an organization to protect public beach use. The people on the other side of that issue were Mike Huckabee and Matt Gaetz.

How do you stay on top of DeSantis and this migrant operation?
This is all happening locally. Somebody gave me a tip that plane was coming in the other night and I did my due diligence. I have people sending me all sorts of things. I have former FBI agents sending me everything they know about these people β€” just this firehose of data on all these people who are involved, the vendor. It's just a ton of shit.

What is it about this that is so egregious to you?
You have here in my backyard an apparatus that is involved in transporting kids and women and fathers and mothers and pregnant women and picking them up and moving them around like chattel for political purposes. There's no way that won't strike at the heart of me, considering what my family has been through. If these people were white, DeSantis wouldn't be doing it to them. If these were Scandinavians or Norwegians or Finnish people, we wouldn't be having this discussion. That makes it no different from when you put yellow stars on their arms and imprint numbers on their skin. This isn't just altruism. This is survival.

How do you think this is going to end for DeSantis?
He got a class-action lawsuit in Massachusetts. Those Boston lawyers are serious. They are going to rip his throat out. He's gonna get crushed up there. Good luck with a jury in a human trafficking class action suit in Massachusetts.

And he's got a criminal investigation in Texas. I think there's possible kidnapping, human trafficking. He knows I'm up his ass. Maybe he'll move on to another stunt. I think the plan was to do this for a while, to run these planes repeatedly. I think they're concerned about using this airport anymore because they know I'll find out. I think it's too much heat. He flew an empty plane on Wednesday [to New Jersey]. There was too much heat to put people on there.

It's like a bank robber, How far are you gonna push the envelope? It's like the movie Heat: "Is it worth the stretch to do another run?" There's a lot of heat. Is it worth the stretch? He needs to win this election. It diverted people from talking about abortion β€” that's good for them. It gets people talking about immigration β€” that's good for the base. Is it worth the stretch to keep pushing it?

How far do you take it?
Ron DeSantis is a seriously sick person. He enjoys dehumanizing people, humiliating people, punishing people. That's a very dangerous person. So I have an obligation to my family, to my friends, to my fellow Floridians, to mankind to shine a light on this man's character and deeds. Because I couldn't sleep at night if I didn't.
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Journalist Bob Norman has been raking the muck of South Florida for the past 25 years. His work has led to criminal cases against corrupt politicians, the ouster of bad judges from the bench, and has garnered dozens of state, regional, and national awards.
Contact: Bob Norman