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

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.

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