By Ashley Cox

(CW44 News At 10 | CNN) — Fifteen minutes into a recent Sunday service, a man in a trim pinstriped suit with coiffed white hair and a blue disposable mask strolled to the front row of The Fountain church and began nodding along to a live and loud contemporary gospel band. “Is that Charlie Crist?” Virginia McNair, a local retiree, whispered from a few rows back at this predominantly Black church. “My favorite.”

It was Charlie Crist — that instantly recognizable, enduring enigma of Florida politics — in his element: campaigning. At age 65, Crist, currently serving his third term in the US House, is running for governor, a job he first won in 2006 as a Republican, left after losing a 2010 US Senate race as an independent, and failed to win back in 2014 as a Democrat. And he’s doing it the only way he knows how: by trying to shake every hand in the state. In 36 hours, he attended the Sunday service, spoke to parents of children killed by gun violence, huddled with Nicaraguan refugees, lunched with Haitian American Democrats and toured Cuban American businesses in Little Havana with his new fiancée.

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Democrats in Florida, entirely shut out of state government for more than two decades, are desperate for power to slow the state’s rightward lurch, but they face a fundraising juggernaut and rising GOP star in Gov. Ron DeSantis. Meanwhile, the country is souring on President Joe Biden, and some Democratic candidates are distancing themselves from their standard-bearer heading into the midterm elections.

Crist, though, is not just embracing Biden, he is channeling the President’s campaign playbook. Like Biden in 2020, he’s running on reestablishing civility, a bet that enough independent and moderate GOP voters are exhausted by the divisive politics of the incumbent Republican administration. Crist is playing up his bipartisan background — at times, even leaning into his Republican roots — in hopes voters will rally around a familiar face with a track record of working across the aisle.

A year ago, Crist’s entrance into the race was met with a sigh from many state Democrats ready for younger blood and fresh faces. But as mail ballots for the August 23 primary are sent out in many Florida counties, party forces have coalesced around Crist’s strategy. With about five weeks left before the primary, Crist has built a solid fundraising advantage and has endorsements from more than 100 elected Democratic officials and the backing of labor unions and progressive leaders alike.

Crist on Thursday released his first statewide ad of the campaign focused on DeSantis — not his main primary opponent, state Agriculture Commissioner Nikki Fried. In another sign Crist is already readying for the general election, his campaign has made an eight-figure reservation of airtime for the fall, CNN has learned.

“Whoever has the best chance is who we have to nominate,” said state Rep. Carlos Guillermo Smith, an Orlando Democrat and LGBT leader who endorsed Crist last month. “The stakes are just too high.”

Biden framed the 2020 race as a “battle for the soul of America.” Crist, who has mentioned the Golden Rule at campaign stops for more than a decade, framed the race as “not right versus left, it’s right versus wrong.”

“There’s a similarity, of course,” Crist told CNN. “Good experience, caring heart — I think people are hungry for that.”

“But I’m a Floridian,” he added. “And, God bless the President, but he’s from Delaware.”

Thomas Kennedy, a Miami activist and Democratic National Committee member known for disrupting DeSantis events, said he thinks Crist is a good foil for DeSantis, a conservative favorite who has brought former President Donald Trump’s confrontational style to Tallahassee.

“People are tired of the toxicity and partisanship,” Kennedy said at the event where Crist vowed to help Nicaraguan immigrants gain temporary protected states to remain in the US. “There’s so much meanness in the state right now. He’s similar to Biden.”

Not everyone is on board. Fried, the lone Democrat in statewide elected office, has built her campaign around the promise “Something new.” Her allies are quick to point out that Crist as the Democratic nominee in 2014 couldn’t beat then-Gov. Rick Scott and that though Biden’s strategy proved successful in his 2020 race, he lost Florida to Trump by a healthy margin. Fried, meanwhile, won office four years ago in a cycle that saw all other Democrats running statewide lose.

“The definition of insanity is doing the same thing and expecting a different outcome, and our party has a history of that insanity,” said Evan Ross, a Democratic consultant and Fried supporter with deep ties to South Florida’s large Jewish community. “Charlie Crist would be the pinnacle of it. If we’re crazy enough to nominate him, I think it will be one of our worst losses in state history.”

Crist dismissed 2014 as a bad year for Democrats everywhere. He noted that he lost the race by less than 1 percentage point and has since outperformed the top of the Democratic ticket three times en route to winning his purple-hued House seat in the Tampa Bay area. Crist’s advisers have also vowed a robust campaign by Democrats this year, unlike 2020 when Democrats acknowledge Biden was more focused on other battleground states.

Asked what he had learned from his last statewide defeat, Crist responded: “Go to north Florida more.”

But even some Crist supporters question if his brand of politics can win a head-to-head battle against DeSantis, who is seeking a blowout victory to bolster his resume before a possible 2024 run for president.

“All of Charlie’s success was by being nice. And that works until it doesn’t. The Republicans, they don’t play around,” said John Morgan, an Orlando lawyer and longtime friend of Crist. “There’s not a mean bone in Charlie’s body. DeSantis is a brawler with brass knuckles in one hand and a switchblade in the other.”

CNN has reached out to DeSantis’ campaign for comment.

 

Retail politics 101

 

On the Saturday before his church appearance, Crist donned a traditional Cuban guayabera shirt and roamed the festive streets of Little Havana in Miami wide-eyed and curious, despite it being an iconic stop for past Florida campaigns, including his own. A Cuban band had serenaded him and Arizona Sen. John McCain there in 2006. He paraded through it in a convertible in 2007. He opened a campaign office there in 2014.

Inside a Cuban coffee shop, Crist watched a worker roast beans and then introduced himself to patrons, including Matt Granat, a graphic designer from Palm Beach Gardens, who had identified the former governor from across the room. Out of earshot from Crist, Granat told CNN he was leaning toward voting for Fried.

“She strikes me as someone who has been a thorn in the side of DeSantis,” Granat said. “He’s switched parties, so I’m not sure about him.”

Ten minutes later, Crist returned after meeting a dozen other people and handed Granat a bumper sticker. “Matt, I want you to have this.”

Granat looked impressed: “Wow, he remembered my name.”

“You need name ID to do this thing in a state this size,” Crist later told CNN. “It’s hard to be recognized unless you’ve done what I’ve done.”

As Crist leans on old connections and a personal touch, Fried has built on an online following through late-night Twitter chats with her audience, sharply edited videos highlighting Crist’s Republican past and capturing viral moments on the campaign trail. The two will debate for the first and only time on July 21.

“Charlie has been doing this for 30 years. He has relationships that go back decades,” Fried said. “And a lot of my relationships are newer and people know I’m not a typical Democrat, meaning I stand up for things differently, I talk differently and I don’t play internal party politics. And unfortunately that’s what Charlie does. I don’t play games. He offers positions to people, he cuts deals, and I’m not willing to do that.”

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Fried has seized on the Democratic outrage over the US Supreme Court eliminating the federal right to an abortion to jump-start a campaign that has been beset by staff shake-ups, lackluster fundraising and an ethics complaint over past income disclosures. She said that as a woman, she is uniquely situated to capture this reinvigorated wave of energy from Democratic voters.

“I’m talking to a lot of women from across the state,” Fried said. “They’ve all turned to me with a collective voice, saying, ‘You have to win, you’re our protector and our fighter.'”

Crist, meanwhile, has a complicated and conflicting history on abortion. He has called himself “pro-life” in the past. He explained to a Florida television station earlier this year, “I’m still pro-life, meaning I’m for life. I hope most people are.” He recently said he regretted appointing to the state Supreme Court a pair of justices who have ruled to uphold abortion restrictions.

Yet, Crist has been a reliable vote for abortion rights in the House, and he has secured endorsements from Barbara Zdravecky, the former CEO of Planned Parenthood of Southwest and Central Florida, and Alex Sink, the state’s former elected chief financial officer who founded an organization that recruits and trains Democratic women who support abortion rights to run for office.

“I just think he’s certainly best prepared to be governor and do the things we need him to do,” said Sink, who lost a bid to succeed Crist as governor in 2010. “But also he’s best prepared to win and raise the money to wage the fight against DeSantis.”

State Rep. Anna Eskamani, an outspoken advocate for abortion rights, was publicly dismissive of Crist’s gubernatorial run when he first announced in May of last year, tepidly calling him “better than DeSantis.” But Crist worked to convince her of his progressive bona fides. They held events together to oppose a state bill that would curb residential solar power and to fight DeSantis’ tax policies. Eskamani was surprised how many people who showed up knew Crist.

“That name ID, of course, it can trigger different emotions, there’s that trust there and it reminds me of Joe Biden,” she said. “I definitely didn’t predict we would be there, but this is Florida.”

 

Leaning on Black voters

 

Much as Biden did, the Crist campaign is banking that his familiarity with Black Floridians will carry him through the primary. Black voters make up 30% of registered Democrats in the state and have been instrumental in determining the party’s nominee in past elections.

Despite earning the moniker “Chain Gang Charlie” for championing the return of chained prison work crews as a state senator in the 1990s, Crist has built long-standing connections with African American and Caribbean American state leaders. At the lunch with Haitian American Democrats, state Rep. Marie Paule Woodson, who was born in Haiti, gave a full-throated backing of Crist and laid out the stakes for November.

“If you don’t wake up and help Charlie be the next governor, every single one of you will be sitting in the back of the bus,” she said.

Crist backs legalization and decriminalization of marijuana and has promised to restore the voting rights of felons who have served their sentences. But as he positions himself for the general election, Crist has also sought to distance himself from some of the more divisive rhetoric on policing from his party’s left flank.

At a breakfast hosted by Florida Parents of Murdered Children, a predominantly Black advocacy group for families victimized by homicide, Crist received an unexpected turn at the lectern, when he called on the room to recognize a table of police officers. He promised as governor to put funding into law enforcement to stop “these horrible crimes that happen all over our country.”

“We know that sometimes, you know, strange things have happened in law enforcement like in Minneapolis, and George Floyd, but you’re good,” Crist said to the table. “You’re good.”

Aramis Ayala, Florida’s first Black state attorney and the event’s keynote speaker, appeared stunned by Crist’s remarks. Ayala, who earned a reputation as a reformer, once published a list of officers who couldn’t be trusted to testify in criminal cases. During her turn at the microphone, she called out the “mass incarceration of Black and brown people.” By then, Crist was on his way to his next event.

Asked by CNN about Crist’s remarks, Ayala, who is running for Florida attorney general, said: “Each person has to have their own message. If he’s the governor, he has to explain what he’s going to do, and I must explain what I would do.” She declined to say which Democratic candidate she intends to vote for in August.

Fried has earned the endorsement of the Democratic Black Caucus of Florida and the Florida College Democrats, signaling that her campaign has gained a foothold with the party’s grassroots.

Camara Williams, a Florida attorney and community organizer, recently hosted both candidates on his Black culture and politics podcast. He told CNN he was unimpressed by Crist’s folksy one-liners and thought the Democrat was relying on a dated mentality for getting Black voters to the polls. Crist said he would bring former President Barack Obama to campaign for him.

When Williams suggested some Black voters think DeSantis has helped their economic standing by keeping businesses open during most of the pandemic, Crist scoffed.

“Doubtful,” Crist said. “Not for you.”

“I’ve heard Black voters say that,” Williams responded.

“That’s crazy, man,” Crist replied. He ultimately cut the interview shorter than the requested hour.

Williams this past week endorsed Fried. The two clicked during a wonky 70-minute interview that touched on Black farming, generational wealth and marijuana policy. In an interview last month with CNN, Williams said he felt Crist lacked authenticity and was underestimating DeSantis.

“He may hold a fond place in some African American voters’ hearts, but if you think that’s going to bring tailwinds to get people interested in your campaign, you’re wrong,” Williams said. “DeSantis will do a good job of messaging to a certain sector of Black voters because of economics. You have to address that.”

Crist shrugged off the criticism. Black voters know him, he insisted.

“I’m sorry he feels that way,” Crist said of Williams. “He has a right to his opinion. But he doesn’t know me.”

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