The Hard-Tweeting Defense Lawyer GOP Candidates Have Learned to Fear

SARASOTA, Fla. — Ron Filipkowski sat at a table in the Sarasota courthouse waiting for the judge to call his client’s name, when the urge to pull out his cell phone finally overcame him.

The docket was stacked that day and he had time to kill. So, he did what he often does: checked X, formerly Twitter. 

His eyes began to scan. His fingers moved into place. Filipkowski saw that former Vice President Mike Pence had turned down an invitation to appear at a Georgia GOP convention where Donald Trump was slated to appear as the keynote speaker. He dashed off his take.

“Pence is afraid to be at an event together with Trump. Mother isn’t ready for that much stress yet,”Filipkowski tweeted, referring to the myth that Pence calls his wife “mother,” which Pence aides have denied. Ping! Nine hundred four likes.

A few minutes passed before he posted his next tweet: He shared a photo of Ivanka Trump in a blue gown talking to Prince William at the wedding of the Crown Prince of Jordan; it had originally been published by a British stock photo agency and had not yet been shared widely. Ping! Four hundred fifty-one retweets and a slew of outraged comments asking what the former first daughter was doing there.

Eventually, the judge announced Filipkowski’s client’s case. He put his phone back in his pocket and readied his defense of a man who drove the getaway car for a burglary that was recorded by security cameras. Wearing an orange jumpsuit from prison, his client pleaded no contest. Filipkowski resumed tweeting in the afternoon.

Filipkowski’s life is split between the offline and the online one. Offline, Filipkowski, 54, is a low-profile criminal defense attorney arguing cases involving drug possession or drunk driving. He works from a tree-shaded single-story office building just a few blocks away from the courthouse. And when he’s not in his suit and tie, he’s often sporting sneakers and a golf polo: an everyman garb that seamlessly blends in with the Florida crowd.

Online, Filipkowski, a former Republican now devoted to trolling the GOP, is a different person altogether. He is a social media obsessive — or savant, or both — sharing an endless stream of photos, videos, political dirt and, at times, biting political commentary with the roughly 750,000 followers he has on X, sometimes blowing up a politician’s comment or gaffe with attention. “The thing that I think is so unique about Ron's work is that he surfaces a lot of clips and photos that aren't things you can find by just watching cable news or YouTube streams,” said Aaron Rupar (follower count: 884.7k), a liberal-leaning journalist known for quickly clipping political videos that go viral on X. “He's great at dredging things up from deeper social media sources that take a lot of work to find.”

During the 2022 midterm election, he shared a video of Pennsylvania Senate candidate Dr. Mehmet Oz talking about preparing a crudité platter that went viral and underscored voter concerns that the wealthy TV physician was out of touch. During the same cycle, he picked up on then-Senate candidate J.D. Vance telling Steve Bannon’s War Room podcast he didn't “care what happens to Ukraine one way or another,” a moment that previewed the shift in how Republicans view foreign conflicts. Days later, Vance’s campaign issued a statement clarifying his comments. And earlier this year, when 2024 GOP presidential candidate and Florida Gov. Ron DeSantis lashed out at a reporter during a trip to Jerusalem over a question about his time serving at Guantanamo Bay as a Navy lawyer, Filipkowski posted a clipped video of the moment that now has over 3.8 million views.

His tweets have sparked cable news segments and online battles with political operatives. Journalists have alerts turned on to catch the latest photo or obscure right-wing event he has uncovered. Even the campaigns he covers and political figures he loathes have warmed to him and even teamed up with him. Filipkowski said he is in contact with far-right activist Laura Loomer and people affiliated with Donald Trump’s campaign. It’s not to boost Trump (whom he has been agitating against since the 2020 campaign) but to upend their mutual enemy: DeSantis.

“I’m probably the top anti-DeSantis person on Twitter. So if [rivals] have something anti-DeSantis that they want to get into the mainstream, they’ll send it to me,” Filipkowski said, without disclosing the name of anyone on the Trump campaign he’s worked with. The Trump campaign declined to comment. 

Loomer said they speak occasionally. “He knows I’m a Trump loyalist, and I know he doesn’t like Trump, and despite our differences, we have found common ground on making sure Ron DeSantis is never elected president of the United States, ever.”

In an era of siloed social media, where the left and right burrow into their own echo chambers, and where candidates bypass nonpartisan media and instead gravitate toward podcasts and Twitter spaces with sympathetic interlocutors, Filipkowski is filling a new kind of role. Part opposition researcher, part snarky opinion writer and part journalist, he’s poring through hours of online audio and video footage, often from deep inside these ideological bubbles, to pull out the most newsworthy clips and slingshot them out at a wider audience. Bolstered by Filipkowski’s cred as a former Republican himself, those clips frequently go on to become campaign headaches, and ahead of 2024, he plans to do even more damage.

He’s built it all in just a few years, working for free while juggling the demands of his law practice. Filipkowski is trying to pivot to doing his online work full-time, though. He recently teamed up with MeidasTouch, a “pro-democracy” website, to launch his own podcast and work as editor-in-chief of an online publication that will showcase his digging. The website had a soft launch at the beginning of August that attracted over 2.5 million viewers in the first week, according to a press release.

Filipkowski has built his new career around a singular mission — to document, and hopefully help reverse, the forces of fraud and incompetence that he thinks are reshaping the party he once loved. But he’s also discovering the online ecosystem he’s now a part of can be just as vulnerable to greed and grift. He’s still figuring out how to navigate it and make a space for himself within it where he doesn’t have to compromise on what originally motivated him — all while, for now at least, trying to keep his online life from creeping into his offline one.

“Are you Ron Filipkowski?” one man asked him as he waited on an elevator to take him to his second hearing of the day. “I follow you on Twitter."

Filipkowski seemed bashful about being recognized. “Yeah, it’s me,” he said with an awkward smile before stepping on his elevator ride up.

Not long ago, Filipkowski was a card-carrying member of the GOP. He was twice elected president of the Republican Club of South Sarasota County — one of the most influential GOP clubs in the state — and he ran on the Republican ticket for public defender in 2008. He was appointed twice by Florida Gov. Rick Scott and once by Ron DeSantis to Florida’s 12th Circuit judicial nominating commission.

Filipkowski says he was drawn to the Republican Party while he was serving as a Marine. The working-class son of a single mother, he worked to pay his way through college and was attracted to the kind of pull-yourself-up-by-your-bootstraps, small-government conservatism popularized in the 1980s. His conservative identity was so pronounced that he and his wife named their first son Ronald Reagan Filipkowski.

But that changed during the Covid-19 pandemic. Forced to stay at home and stop training for triathlons, a longtime passion, he watched the Trump White House briefings and found himself increasingly angered by what he was seeing.

“A lot of Republicans talk about the fact that with Covid they were forced to see what their kids were being taught at school,” Filipkowski said. “For me, it was like, now I'm forced to watch Trump every day, and I just started throwing things at the TV and screaming. … I was shocked at how stupid he was and how obnoxious he was.” That’s when he decided, he says, “I'm gonna do everything I can to defeat him.”

One day, during the 2020 election cycle, he spotted a call for people to submit personal testimony videos for an advertising campaign by Republican Voters Against Trump, a group longtime conservative Bill Kristol was launching.

“I wrestled with it for like, two weeks. Because I'm like a known person here. You know, once I do that, it’s burning a bridge forever. … I can never walk into a Republican club or meeting again,” Filipkowski explained.

He did it anyway. What resulted was a video of Filipkowski rattling off a list of 20 reasons why he didn’t think the Republican party should support Trump’s re-election.

“I made the case to conservatives, which is like, ‘Why do you like this? … You say that you’re for this military service, [that you’re] Christian who lives right down the line, and [Trump], in every way, has lived his life the opposite of what you believe,’” Filipkowski explained.

The video, part of an ad campaign for the group in spring of 2020, resonated so much that Kristol put Filipkowski on billboards in Fort Myers, Tampa and Orlando.

“He didn't come from the Washington world or D.C. Republican politics,” said Kristol. “He wasn't known to that many people here. He … obviously was a serious lawyer and all that, but he really has made a mark.”

Tim Miller, a former Republican operative who is now at the anti-Trump conservative publication the Bulwark, calls Filipkowski the “Kelly Clarkson” of Republican Voters Against Trump for having a breakout moment after the ad campaign.

A few months later, Filipkowski publicly resigned from his appointment on the judicial nominating committee over DeSantis’ handling of the pandemic in Florida. In his resignation letter, he called DeSantis’ policies “reckless and irresponsible.” His resignation became national news with appearances on CNN and MSNBC as the first DeSantis appointee to quit.

“I thought DeSantis was like competing with [South Dakota Gov. Kristi] Noem over who could open the fastest. … I thought it was going to be a disaster, and it was,” Filipkowski said. “As much as he wants to rewrite history, I remember all the people who died.”

Filipkowski formally switched his party registration from Republican to Democrat on Jan. 7, 2021, at 9 a.m. when the office of the Supervisor of Elections opened. Now, he is on a personal mission to tear down Reagan’s party and prevent Trump, or a Republican like him, from becoming president again.

Many of the Trump allies who prompted his exit from the party now live in or have connections to Filipkowski’s hometown. The oceanside city of Sarasota and the surrounding area has attracted: Trump Media & Technology Group; Rumble, a video platform popular on the right; Michael Flynn; the Overstock founder turned election conspiracy theorist Patrick Byrne; the young conservative leader of Turning Point USA Charlie Kirk; and Christian Ziegler, the current head of the Florida Republican Party.

In an interview from his small office in downtown Sarasota, Filipkowski described how he keeps tabs on the 2024 GOP field, far-right firebrands on the Hill, and maintains a pulse on the soap-opera storylines of conservative influencers and provocateurs in the deepest corners of the web.

There is nothing evident from Filipkowski’s office to suggest that he is so singularly dedicated to his life online. On display are photos of his five adult kids and wife. Snapshots from family trips to Europe. Framed diplomas and certifications. Medals from his time in the Marines. But if you look closer, you can see signs of an obsessive personality, biographical details illustrating that when Filipkowski zeroes in on something — whether it is coaching a Little League team, or doing triathlons, or taking on a political enemy — he becomes all-consumed.

Filipkowski didn’t just coach a Little League team — he led his kids to six state championships, and 13 of the kids on the team received college scholarships to play baseball. Six of them, he claims, including pitcher Eric Skoglund, were drafted professionally, and Filipkowski himself was named National Coach of the Year by Travel Ball Select, a publication dedicated to travel baseball teams. He even published a how-to manual for youth baseball coaches.

Filipkowski also didn’t just run triathlons — he competed in his age group national championship at age 50 and then trained so hard running sprints he caused nerve damage to his foot and can no longer run.

Filipkowski has an encyclopedic knowledge of Republican lawmakers, some of whom he knows personally from his time as a mover and shaker in Florida politics. During our interview, he name-dropped several high-profile Democrats and Republicans he had personal interactions with, but asked for their names to be withheld to preserve those relationships.

Filipkowski is coy about how exactly he mines through hundreds of hours of podcasts and videos to find material about Trump and conservative figures, but he has mentioned the support of an anonymous woman — a suburban mom based in another state — who reached out and offered to pitch in to his online efforts and flag interesting material. While they have since gone separate ways, the two of them previously worked in shifts to comb through far-right media accounts and search through geotag locations at places like Mar-a-Lago or CPAC’s convention halls to map out the MAGA universe.

When he’s not using his free time to record and watch fringe conservative events that aren’t being covered by mainstream outlets, he regularly appears on other podcasts and shows that have cropped up during the Twitter politics era. The June afternoon he was interviewed, he paused to tape an episode of the podcast "Are You F'ng Kidding Me? With JoJoFromJerz” in his office, and he was recently featured on an episode of Showtime’s “The Circus."

His work has also introduced him to some unexpected public figures, like members of Congress or people who have found themselves in the center of media storms.

In the aftermath of the 2022 midterm elections, Filipkowski said he got to know, and occasionally clashed with, Christian Walker, the son of Herschel Walker, who lost in the Georgia Senate race as a Republican. Filipkowski shared video clips of both Christian and his dad Herschel Walker during the campaign, including clips about the Senate candidate’s abortion scandal and his son’s denunciation of his father, but when it was over, Christian Walker and Filipkowski buried the hatchet and formed a relationship. Christian Walker, who has since moved away from politics, confirmed the two have been in contact.

“It’s really, really weird to have relationships now with people who I grew up disliking. And now we're like buddies,” Filipkowski said.

There are others that do similar work to Filipkowski — like the anonymous account @acyn, and Rupar (who tweets under his full name, no space). Both Rupar and @acyn said they are regularly in touch with Filipkowski.

“I view our work, at least in part, as helping decode what's happening on the American right for people who are center or left on the political spectrum,” Rupar said.

On occasion, a hint of frustration becomes evident. Filipkowski’s life has been upended by his mission-like commitment to his X feed. Would it hurt, he wondered aloud during our talk, for the producers and anchors at cable networks to give him the occasional hat tip?

“MSNBC is the worst because literally like a third of their programming is my Twitter,” Filipkowski said. “I mean, like, I don't have an ego about it. I try to take a very Gandhian approach to my social media, which is like no credit, no glory, no nothing, no money. But it does sort of bug you a little over time. Like couldn’t Joy Reid one time go, ‘You know what, like one third of my show is Ron Filipkowski’s Twitter.’”

Filipkowski’s political turn has opened him up to criticism and skepticism. As he discovered himself, finding out who to trust in the broad universe of Never Trumpers can prove trickier than it appears.

His departure from the judicial nominating committee came the day after the authorities searched the home of Rebekah Jones, a data scientist in Florida who claimed she was fired for not manipulating Covid data. He expressed concern with her treatment, suggesting that Jones was being targeted for questioning the governor’s approach to the pandemic.

Later, an inspector-general report concluded that Jones’ accusations were unfounded. She was fired for insubordination before later running and losing in a race to unseat Rep. Matt Gaetz in Florida’s 1st Congressional district.

Filipkowski has been criticized for not criticizing Jones more, although he now describes Jones as a “fraud” and a “grifter.”

After Filipkowski’s new fame as a Never Trumper online personality, it was also hard to figure out where exactly he fit in.

“You have to ask, are their motives pure? Are they just making a lot of money from Democrats? … Because their old way, the bridges are burned, and so that's a legitimate question,” Filipkowski said. “That’s a big reason why I didn’t want to take money. I’m not doing this because I want Steve Schmidt’s house in Utah that he got during the 2020 campaign.” (Schmidt, a co-founder of the anti-Trump Lincoln Project, has been criticized for purchasing a million-dollar Utah home while he was running the PAC.)

As his online and offline lives became harder and harder to separate, Filipkowski has begun imagining a future in which he actually chooses one over the other. He said he’s in the process of moving away from his work as a criminal defense attorney and doing his commentary and documentation of the far-right as a full-time job by November.

He recently launched his own podcast series, “MAGA Uncovered,” which is recorded each week from his tiny office and aims to “expose the extremist propaganda spread via hidden right-wing media, responsible for Republican voter brainwashing,” according to its billing on Spotify.

He’s also joined forces with other influential X authors, like @PatriotTakes, an account that does not disclose the author’s real name, at MeidasTouch. In a statement, Brett Meiselas, co-founder of the MeidasTouch Network, called Filipkowski “one of the most trusted and prolific sources of news today.”

“It’s pro-democracy, partisan news — we’re not hiding that,” Filipkowski said. A lot of people are “tired of CNN trying to present both sides, and I think that should exist, but that’s not what we are,” he continued.

Even as he makes the choice to leave his offline life for his online one, there is a recognition that his work on X has become an all-consuming obsession.

As he showed off family vacation photos in his office, he remarked that the framed photo of the Acropolis might need to change since Ivanka Trump had recently posted a photo of her family standing in front of it on Instagram.

He checks his online feed so much that he and his family set up rules for when he must be offline. He doesn’t talk politics anymore with his family, some of whom are Trump supporters. He’s gained friends but also lost some over his tweets.

“My kids will say people ask, ‘Are you related to that crazy guy on Twitter?’ They’ll be like ‘Yeah, that’s my dad’ or ‘I don’t know him,” Filipkowski said.

But for Filipkowski, this isn’t just about posting embarrassing or outlandish political clips online. He truly believes he stands on the last line of defense against sinister and dark forces.

“This is a fulcrum point in our history where we're either going to continue on and return to a healthy, normal democracy again, and come out of this jam in six or seven years,” he said. “Or I think it's all coming apart and we're moving towards an authoritarian state in which institutions are destroyed.”

“I don’t think I’m overstating it because they say it,” he continued. “I listen to them say it. They’re not bluffing."