TALLAHASSEE — The last time Charlie Crist was considering a run for Florida governor, in 2014, he shared a moment of clarity with one of his consultants.

“He said, ‘Steve, I feel like I can beat the money or I can beat the environment, but I can’t beat them both,’” Democratic consultant Steve Schale said.

Crist would be proven right: He narrowly lost after being outspent by then-Gov. Rick Scott in a historic GOP wave.

Although he might not admit it, both the money and the environment are worse this year as he makes his third run for Florida governor.

Crist, a moderate 66-year-old former Republican with name recognition, fundraising ability and old-school political instincts, has been pulling in support from Democrats as they warily eye a general election against Republican powerhouse Gov. Ron DeSantis.

For many of those supporters, it’s a calculated move: They think Crist has a better chance of beating DeSantis than does his opponent in the Democratic primary, Florida Agriculture Commissioner Nikki Fried.

“He’s like a comfortable pair of boots that will potentially get the job done,” said Fernand Amandi, a Democratic consultant uninvolved in the race.

Whichever candidate wins, the chances in the general are slim, observers say.

DeSantis doesn’t have the personal wealth of former Gov. Rick Scott, who spent $75 million of his own money on his first run for governor, but he does have personal connections to billionaires and about $120 million in the bank.

Florida’s governor’s race has received national attention because DeSantis is a likely 2024 presidential contender. While he needs to win reelection, Democrats face long odds in beating him. The state party is in shambles after decades of failures, President Joe Biden’s approval ratings are historically low, and arguably, its strongest statewide candidate, U.S. Rep. Val Demings of Orlando, isn’t running for governor.

Crist is backed by labor unions and key state lawmakers who point to his recent history as a Democrat. They draw comparisons between Crist’s playbook and Biden’s winning strategy in 2020 as examples of moderation and civility.

Fried, however, has revived criticisms that Crist has faced since he left the GOP: that he’s anti-abortion, a conservative and someone who hasn’t won a statewide race as a Democrat.

Whether Crist’s skills are relevant in 2022 is an open question.

Schale found Crist’s analysis of his chances in 2014 an articulate summary of what he faces again.

“He described it also as running headfirst into a meat grinder.”

Many roles — and identities

No one serving in public office in Florida has a record like Crist’s: On the ballot in 16 elections over 34 years, receiving more than 16.5 million votes and elected to five different positions, as state senator, education commissioner, attorney general, governor and congressman.

There’s one reason he keeps doing it, those who know him say: He genuinely likes running for office and being in office.

His ability to connect with voters is legendary. His political opponents have remarked at what a nice guy he is.

He even seems to enjoy the parts of politics many candidates despise, such as fundraising and confrontations, said Katie Bohnett, who worked on his campaigns between 2006 and 2016 and was his scheduler while he was governor from 2007-2011.

She’s been in restaurants with Crist when he would hear someone “talking trash” about him. Instead of ignoring the heckler, Crist would engage the person by asking friendly questions or offering a handshake, catching the person off guard.

“I just think it’s in his DNA,” Bohnett said. “I don’t know what else he would do.”

But Crist’s retail political skills have long contributed to a perception that he’s an opportunist or just a typical politician. His leadership style has been described as a “shrewdly timed brand of populism.”

Crist was an attorney and state director for U.S. Sen. Connie Mack, who helped usher in the last three decades of Republican dominance of state politics.

When Crist was elected at age 36 to the state Senate in 1992, the chamber was deadlocked 20 to 20, ending the Democrats’ longtime control over the Senate.

He campaigned as the “choice for change” against the longtime Democratic incumbent, and his platform was politically bland: efficient government, quality education, ethics and the environment.

“He plays the game the way it was taught to him by Connie Mack’s people,” Jeff Huenink, the Clearwater Republican state representative who lost to Crist in the 1992 Senate primary, said in 1995. “That is to be non-offensive yourself, stick to the motherhood and apple pie issues, and when necessary distort your opponent’s record.”

In the Legislature, Crist later seized on the bipartisan national anti-crime wave of the 1990s.

In 1995, he sponsored the Stop Turning Out Prisoners act, which made prisoners serve at least 85% of their sentences. (It passed the Senate unanimously and was allowed to become law by a Democratic governor, Lawton Chiles.)

“Criminals can’t commit crimes from behind bars,’’ Crist said at the time.

Crist also got the Department of Corrections to start a chain gang program, following Alabama’s revival of the long-inhumane practice of chaining inmates together to carry out hard labor in public.

Even the Department of Corrections balked at the idea. Florida used to shackle inmates at the ankles, but did not shackle inmates together, a practice that ended in 1967 when a roadside barracks housing more than 50 men burned, killing 38 inmates whose shackles prevented them from escaping.

But Crist pursued the issue publicly, even pushing to allow the chain gangs to work alongside highways.

The effort earned him the nickname “Chain Gang Charlie.” Trying to capitalize on his name recognition, he ran in 1998 for U.S. Senate against incumbent Bob Graham, the widely popular former governor. Crist lost by 25 points.

Willing to buck GOP

Crist wasn’t afraid to at times buck his party — gently — on key populist issues.

He publicly supported a woman’s right to an abortion when he ran for office in 1992. He publicly acknowledged climate change. He was willing to take on utilities and insurance companies, traditionally major campaign donors to GOP candidates.

In 1997, he sued Florida Power Corp. (which eventually morphed into Duke Energy) over a proposed $88 million rate increase, which contributed to the company refunding customers instead. The next year, he filed a bill in the Legislature to allow customers to choose their electricity provider.

Florida Power Corp. accused him of trying to “capitalize on statewide publicity in his campaign to unseat current U.S. Sen. Bob Graham.” Lobbyists in Tallahassee mocked him by handing out a mock “prospectus” seeking investors in “The Charlie Crist Publicity Futures Fund.”

When he was elected governor in 2006, Crist incurred the wrath of insurance companies when he called a special session in 2007 to address a property insurance crisis caused by a wave of hurricanes in 2004 and 2005.

The state, much as it is today, was seeing record homeowners insurance rate increases and companies shedding policies.

Crist was not a detail-oriented policy wonk like his predecessor, Gov. Jeb Bush, said Kevin McCarty, Florida’s insurance commissioner from 2003 to 2016.

But Crist understood the big picture — the need to lower rates — and he was willing to challenge GOP orthodoxy and the interests of the insurance companies, McCarty said. The 2007 legislation was anything but free-market: It had the government absorb more risk for hurricane damage so insurers could lower rates, and it expanded the state-run Citizens Property Insurance to make it a competitor to private insurers.

“I think it was a courageous call,” McCarty, a Republican and self-described “free-market guy” said. “State Farm (in 2009) threatened to leave the state, and Charlie said, ‘Good riddance.’”

Rates overall went down the next two years, State Farm ended up staying, and the market stabilized for about a decade.

‘Consistently inconsistent’ on abortion

At other key times, however, Crist would avoid hot-button topics or change his positions.

When the debate over stem cells was raging, he took a middle-of-the-road position that would offend no one. During the debate over the fate of Terri Schiavo, the St. Petersburg woman who was in a persistent vegetative state, Crist, as attorney general, kept quiet despite opposing the Legislature’s controversial bill requiring judges to keep her alive.

And while running for the GOP nomination for governor in 2006, he shifted to a more conservative stance on abortion, saying he was “pro-life.” In explaining his stance, he’s been “consistently inconsistent,” defining the terms “pro-life” and “pro-choice” in his own way, according to the website Politifact.

Fried has seized on Crist’s inconsistencies on abortion, calling herself the only candidate who has been pro-choice their entire life. She pointed out that Crist appointed Charles Canady — who had sponsored the partial-birth abortion ban in Congress in the 1990s — to the Florida Supreme Court. The Court is likely to hear a challenge to Florida’s new 15-week abortion ban; Crist recently said he regretted appointing Canady and said he would not vote to keep Canady on the court.

But Crist has won over a diverse coalition in the primary that includes state Rep. Anna Eskamani, D-Orlando, one of the Legislature’s most prominent Democrats and a former senior director for Planned Parenthood of Southwest and Central Florida.

Notably, two organizations dedicated to electing pro-choice women, Ruth’s List and EMILY’s List, have not endorsed either candidate in the primary.

Eskamani said that Crist, despite being a former Republican, has a stronger history on consumer issues than does Fried, a former corporate lobbyist who in 2019 angered environmentalists for supporting utilities such as Florida Power & Light and Duke Energy Florida, which were asking the state to sharply lower or eliminate energy conservation goals. In Congress, Crist was a consistent supporter of reproductive rights, she added.

Eskamani said Crist won her over by frequently asking her advice and absorbing some of her policy recommendations. She said she also noticed his diverse coalition of local Central Florida supporters that included people who had known Crist for a long time.

“It’s really hard to find politicians that 10, 20 years later, you still like them,” she said. “That alone says something about his character.”

‘A governor they can like’

In the primary, Crist has avoided criticizing Fried, saying the race is mostly a referendum on DeSantis, whom he’s called a bully and “not the most pleasant person in the world.”

“I think people like having a governor that they can like,” Crist told the Tampa Bay Times’ editorial board last month.

DeSantis, backed by billionaires and a national profile, has more money on hand than Scott did and is more popular with his base than Scott was in 2014.

Regardless of how Crist fares, some believe he’s not going away.

“People ask me, do you think Charlie’s done if he doesn’t win? I don’t,” said Schale, his former adviser. “He’s the phoenix in the ashes. He’s going to bounce back. He’s going to find some outlet.”