The loudest #NeverTrump voice is Florida Republican Rick Wilson

He emerged as a leading critic during the 2016 campaign and he has not let up, becoming a national figure through an incessant Twitter feed, outraged-fueled cable news appearances and as a columnist who mixes salty humor with serious viewpoints.
Rick Wilson at a Tallahassee television studio late at night for a CNN live "hit." (Alex Leary  |  Times)
Rick Wilson at a Tallahassee television studio late at night for a CNN live "hit." (Alex Leary | Times)
Published Jan. 28, 2018|Updated Jan. 29, 2018

TALLAHASSEE — Just before 11 p.m. on a Thursday night, a black SUV pulls up to a television studio here and delivers a bald, middle-aged man in a blazer, khakis and L.L. Bean moccasins. He drinks Diet Coke and climbs into a tall chair, waiting for the "hit."

Moments later, live on CNN, Rick Wilson does his thing, reveling in the defeat of Alabama Senate candidate Roy Moore, whom he brands “Judge Perv.”

President Donald Trump might appreciate Wilson’s pithy venom, except that Wilson has become one of the country’s foremost anti-Trump Republicans. Besides, Trump endorsed Judge Perv.

"Rick is slaughtering as always," a man writes on the live streaming service Periscope, which Wilson has set up on his iPad so his followers can watch him in the studio.

This is no moderate. Wilson, who lives in Tallahassee, is a longtime conservative operative with a burn-it-down appetite for conflict matched only by his affinity for guns and good food. He has used social media and cable news appearances to wage war against a man he sees as a con and a cancer on the GOP. Or, as he described the president last week to his nearly 300,000 followers on Twitter, "a serial fabulist and short attention-span mental lightweight."

Beyond a shared affinity for Diet Coke, Wilson and Trump understand that being loud and unfiltered attracts notice. A handful of prominent GOP critics of the president have emerged but none as colorful as Wilson, 54, who bears a resemblance to Mike, the assassin and fixer on Breaking Bad. He carries a pistol in the small of his back.

"I started doing it religiously after all the death threats," Wilson said.

A growing national profile has allowed Wilson to pursue a documentary film, Everything Trump Touches Dies, which has drawn tens of thousands in online donations and began shooting this month, and he is writing a book. Friday brought his fourth appearance on HBO's Real Time with Bill Maher.

Such outspokenness at a time when many Republicans have accepted Trump, or muted their objections, risks Wilson's bread-and-butter work as a campaign operative, which began as a Florida field director for George H.W. Bush in 1988 and has included work with Rudy Giuliani, Katherine Harris and Marco Rubio. He has produced super PAC ads in 38 states and long been a go-to quote for political reporters.

But Wilson, clearly relishing the spotlight, keeps swinging. His constant Trump vilification puts him in the unusual position of having legions of Democratic fans alongside #NeverTrump Republicans, while drawing him into confrontations that can be as crass as they are entertaining.

"There's not a lot Rick says that I can repeat in front of my mother, but he is a very important voice," said David Jolly, another Florida Republican who sees Trump as dangerous to the party and the country.

"There's a Hunter S. Thompson quality to Rick in his voice and his writing. He resonates across the aisle because he's not doing the gauzy Washington 'take' and being careful not to offend," said John Avlon, editor-in-chief of the Daily Beast, where Wilson produces a widely-read column. "Agree or disagree, you've got to respect that."

• • •

Most Americans probably know Wilson as the guy on CNN or MSNBC — he does up to four "hits" a week — who spars with Trump supporters and spits fire at the controversy du jour. YouTube is full of these exchanges.

Hours after Trump referred to Massachusetts Sen. Elizabeth Warren as "Pocahontas" during a November ceremony honoring Navajo Code Talkers, Wilson was on TV blasting White House Press Secretary Sarah Huckabee Sanders for defending Trump, saying she "tries to bury people in an avalanche of horse—-."

Mike Shields, a straight-laced Republican commentator for CNN, grimaced at the profanity while Wilson kept going. "I mean, she probably has some tiny, shriveled husk left in her soul where she realizes this is the wrong thing to do," he said. "But she does it anyway because otherwise they'll replace her."

Shields: "Rick, your arguments as a critic of the president would be more cogent if you didn't make them so personal and angry and start calling people congenital liars when they are doing their job."

Wilson: "Well, Mike, it's harsh, but she is."

Asked to comment on Wilson, Huckabee Sanders responded, "Rick who?"

Some Republicans see Wilson as a loudmouth opportunist. "He is the Kim Kardashian of GOP politics," said Florida GOP strategist Mike Hanna, who did work supporting Alabama's Moore. "He bashes Trump for being arrogant, self-serving, crude — on CNN and MSNBC no less — and for being in love with his own celebrity status. Where would Rick Wilson be if there were no Trump?"

Insists Wilson, "The delta between who I am on Twitter and in real life is zero."

"He's always been provocative," said Steve Schale, a Democratic strategist who became friendly with Wilson through exchanges in the early years of Twitter. "I had friends say, 'How in the world can you get even within 5 feet of that guy, he's horrible.' Now people see him as a principled figure. The Rick on Twitter can be bombastic and combative, but he's also the kind of guy you can sit on the back porch with and enjoy a glass of pinot noir."

• • •

Frederick George Wilson was born in Tampa, the son of a CPA and a housewife who would later go to college to become a hydrogeologist, her son tagging along and reading books in the USF library. "They were liberal Democrats," Wilson said, noting his parents, like many moderate Southern Democrats of a certain age, are now Republicans.

"We were a family of incredible talkers, readers, arguers," Wilson said. Three days before his mother birthed him in November 1963, she went to see President John F. Kennedy in Tampa, and four days after came the tragedy in Dallas.

The election of Jimmy Carter, Wilson said, had a transformative effect. An uncle in Winter Haven took him to a Ronald Reagan campaign event and Wilson remembers a staffer picking a few leaves off the lawn. "It showed the importance of the scene, the set."

"I didn't have the immediate sense of, 'Oh, I must be a conservative,' " Wilson said, but Reagan's talk of American strength and honor stuck.

He went to George Washington University and got a start in politics as a volunteer for Connie Mack's 1988 U.S. Senate campaign, switching to a paying job with Bush's presidential campaign as a Florida field director.

That led to a communications job in the Pentagon. Bill Clinton's 1992 victory sent Wilson back to Florida and he linked up with Adam Goodman, now a prominent campaign ad maker. It was an opportune time to be a Republican in Florida. "We elected a whole s—load of them," Wilson said.

Out-of-state candidates began calling, including New York Mayor Rudy Giuliani, who was running for a second term. Wilson took a full-time job in the administration, where he studied the aggressive ways of New York politics and honed his TV chops on NY1, the city's 24-hour news channel.

"The decision to stay on with Giuliani was a tremendous career choice," Goodman said. "It gave him the freedom to stand out on his own. Rick has never been a country club Republican. I think he's been incredibly successful in getting attention and showing maybe there's a beginning of a third way in politics."

Wilson, who worked with independent, long-shot presidential candidate Evan McMullin in 2016, says the party needs to move on from battles over marijuana and gay marriage and must reach out to a more diverse electorate. The recent tax bill, he said, confirmed the party's allegiance to donors over regular people.

He draws a line with guns, saying Democrats have lost that cause. Wilson has about 60 of them, including assault rifles he hand-built and fires off in the backyard of a home set in a woody part of Tallahassee. On his kitchen table one evening in December, a Sig Sauer handgun lay in a fruit bowl as Wilson chopped mushrooms, Jilly and Riley, his German Shorthaired Pointers hovering. He regularly hosts dinners for friends from across the political spectrum and freewheeling discussions take off as the wine flows.

"Here's what we're going to do," Wilson said, bending down to open an AGA oven that is so heavy the kitchen floors needed reinforcing. "We're going to cook these pork roasts and we've got thyme and shallots underneath them and the fat's going to melt down. We're going to make a little mushroom gravy with pancetta. And I've got shaved brussels sprouts. Bang, bang."

The group ranged from a lobbyist to a former top aide to Rubio. "Just so you guys know, we went into Alabama this week," Wilson said. He was referring to ads he produced for an outside spending group that targeted Moore. Wilson grabbed his iPad and played the ad, which featured the faces of young women, and asked, "What if she was your little girl?"

• • •

Wilson created one of the most talked about ads in the 2014 midterm elections with a spot that painted President Barack Obama as a bad boyfriend. "I know I'm stuck with Barack for two more years," a woman said, "but I'm not stuck with his friends." In 2008, he produced an attack ad featuring the incendiary words of the Rev. Jeremiah Wright, Obama's one-time pastor.

Other ads have generated significant controversy, chiefly a 2002 spot attacking Democratic Sen. Max Cleland of Georgia. A war hero and triple-amputee, Cleland was portrayed as soft on terrorism against images of Osama bin Laden. The point, Wilson said, was to highlight Cleland's voting record. But critics called it shameful — "worse than disgraceful," said Sen. John McCain, R-Ariz.

That background helps explain Wilson's punchy presence on Twitter. Since joining in 2009, he's fired off more than 258,000 messages, a witty, acerbic stream of thought followed by top reporters and politicians from Debbie Wasserman Schultz to Jeb Bush.

Wilson grasped the power of the medium in 2012 with a tweet composed at Publix. "THIS is why we're doomed. Woman ahead of me in store on her iPhone 5, which SHE IS BRAGGING ABOUT. Pays for groceries with EBT card." It went viral.

His fighting impulses have gotten him in trouble. In 2015, Wilson deleted a tweet in which he asked conservative personality Ann Coulter if Trump paid her for sex, using more explicit terminology. Wilson's wife was "less than fully pleased."

He had been in a long-running war with the conservative Breitbart News over its support for Trump (the publication dismisses him as a "establishment" Republican) and after a heated battle with the site's editor on CNN, Wilson said a reader threatened his adult daughter with rape. Coulter mocked his alarm, calling Wilson "a girl in a pink party dress."

"I tweeted a reply based on parental anger, and with vitriol that made the already ugly divisions on Twitter uglier," Wilson wrote at the time, offering a "sincere apology." In an interview he stressed the apology did not extend to Coulter.

Wilson's battle with Breitbart (officials there did not respond to requests for comment) and the far right has made him a target for harassment and death threats. His children have been trolled. Pizzas and Korans have been delivered. Someone faked a Craigslist ad for a yard sale and Wilson awoke at 5 a.m. to find a man on his back porch, peering through the windows.
"He damn near got himself shot."

• • •

The first year of the Trump administration has been decidedly rocky and an unprecedented number of top aides have quit or been forced out, including Steve Bannon, who unleashed Breitbart's forces on Wilson.

"Bannon once promised to destroy me," Wilson celebrated on Twitter earlier this month. "Oddly, I seem to be the one standing while Hobo Steve wraps himself in trash bags on a sewer grate and downs his last plastic-bottle fifth of Olde Oscelot bourbon."

Yet the GOP is largely getting in line behind Trump, enjoying a strong economy and passage of the tax bill. His administration has swept away business and environmental regulations, torn up trade agreements and is steadily installing conservatives on the federal bench.

"Trump 'accomplishments' are ephemeral, coincidental and accidental," Wilson said, insisting that a party that sticks with Trump is a party facing extinction. A reckoning is coming in the midterm elections, he predicts, though Wilson wrongly said the GOP would lose the Senate with Trump as the nominee in 2016.

"I'm going to keep correcting people, sometimes harshly, on the disparity between conservativism and Trumpism."

Rick Wilson, always on.

"He's the first to point out when the emperor has no clothes — and that's refreshing in this crazy world of Trump apologists who pretend everything is normal," said Sally Bradshaw, a veteran Republican strategist in Florida. "If the GOP has a future — and I think there is a big question mark about that — it will be because of people like Rick."

A draft of Wilson’s new book, Apocalypse Trump, on his kitchen table in Tallahassee, where he often works, fueled by outrage and Diet Coke. (Alex Leary | Times)
A draft of Wilson’s new book, Apocalypse Trump, on his kitchen table in Tallahassee, where he often works, fueled by outrage and Diet Coke. (Alex Leary | Times)