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Running as a Democrat, Crist looks to join the smallest club in American politics

Rep. Charlie CristCharles (Charlie) Joseph CristDemocrat Nikki Fried teases possible challenge to DeSantis DeSantis to hold Newsmax town hall The Hill's Morning Report - Presented by Emergent BioSolutions - Upbeat jobs data, relaxed COVID-19 restrictions offer rosier US picture MORE (D-Fla.) said Tuesday he will challenge Florida Gov. Ron DeSantisRon DeSantisJournalism dies in newsroom cultures where 'fairness is overrated' Five takeaways from new CDC guidance on going maskless Disney examines mask policy, theme park capacity after updated CDC guidelines MORE (R) to win his old job back, attempting a political comeback that would vault him into perhaps the most exclusive club in American politics.

Just three other men have won election as governor of their home states as members of both the Democratic and Republican parties. Crist, who won the governorship as a Republican in 2006, is trying to be the fourth.

He would follow in the footsteps of Mills Godwin, the first person to lead a state under both parties’ banners.

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Godwin won election in Virginia in 1965 as a Democrat, backed by influential Sen. Harry Byrd, a conservative Democrat who ran the commonwealth’s dominant political machine in the middle decades of the 20th century. 

But Godwin was the last in his line as Byrd’s power faded. He was replaced four years later, forced out of office by Virginia’s one-term limit on governors, by Republican Linwood Holton, the first non-Democrat to run the state since William Cameron won election in 1881 as a Readjuster.

Godwin spent his time out of office managing the reelection campaign of Sen. Harry Byrd Jr., who had been appointed to fill his father’s seat and who ran for a full term as an independent. He backed Republican Richard Nixon in the 1972 presidential campaign, and he won the Republican nomination for governor the following year.

Later that decade, Alabama elected Fob James (D) as its governor, near the end of a more than centurylong post-Reconstruction run of one-party Democratic rule of the South. James did not seek reelection in 1982, but he did run in 1986 and 1990, without winning the Democratic primary.

In 1994, he tried to return to office for a third time — this time as a Republican. James rode the Republican wave to stage a come-from-behind victory in November, ousting incumbent Gov. Jim Folsom Jr. (D) to become only the second Republican since Reconstruction to win Alabama’s governorship. 

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The third member of the most selective club in American politics is West Virginia Gov. Jim Justice, the billionaire coal magnate who won election as a Democrat in 2016. Justice took 49 percent of the vote that year, the same day Republican Donald TrumpDonald TrumpFranklin Graham says Trump comeback would 'be a very tough thing to do' Man suspected in wife's disappearance accused of casting her ballot for Trump Stefanik: Cheney is 'looking backwards' MORE won 68 percent of the vote to carry West Virginia’s five electoral votes.

Justice took office in January 2017, five days before Trump, and the two men seemed to strike a bond. Eight months later, Trump stood next to Justice at a rally in Huntington as Justice switched his party affiliation to join the GOP.

Even after switching to the Republican Party, Justice repeatedly clashed with top legislative leaders. But none of the prominent Republicans with whom he fought decided to challenge him, and he easily outpaced Woody Thrasher, the former state Commerce secretary, in the 2020 Republican primary.

Democrats failed to field a prominent challenger. Justice won reelection as a Republican by a comfortable 33-point margin.

Crist will not have the same easy ride, even in his own adopted party. On Tuesday, the same day he formally declared his interest in returning to Tallahassee, Rep. Val DemingsValdez (Val) Venita DemingsDemocrat Nikki Fried teases possible challenge to DeSantis The Hill's Morning Report - Presented by Emergent BioSolutions - Upbeat jobs data, relaxed COVID-19 restrictions offer rosier US picture Democrats cool on Crist's latest bid for Florida governor MORE (D) released a glossy biographical video that seemed to tease at her own future in statewide politics, touting her place on President BidenJoe Biden28 Senate Democrats sign statement urging Israel-Hamas ceasefire Franklin Graham says Trump comeback would 'be a very tough thing to do' Schools face new pressures to reopen for in-person learning MORE’s short list as potential vice presidential contenders and her record as Orlando’s police chief.

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State Agriculture Commissioner Nikki Fried, the only Democrat to hold a statewide office, has also been traveling through Florida taking aim at DeSantis, sending clear signs that she too is considering running for the top job. 

Whichever Democrat emerges from the Aug. 23 primary, just over two months before the November general election, will face an uphill battle against the incumbent. The most recent survey of Florida voters, conducted by the independent firm Mason-Dixon Polling and Strategy, found 53 percent of Florida voters approved of the job DeSantis is doing as governor.

The same poll found DeSantis leading Fried 51 percent to 42 percent, and leading Crist 52 percent to 41 percent. The poll, conducted Feb. 24-28 among 625 registered voters with a margin of error of 4 percentage points, did not test Demings against DeSantis. 

No Democrat has won Florida’s top job since Lawton Chiles (D) beat Jeb Bush (R) to win a second term in 1994. And Florida voters have tended to stick with their governors: The last incumbent to lose a bid for reelection was Bob Martinez (R), who lost to Chiles in 1990.

Those who have succeeded in winning election as members of both parties — Godwin, James and Justice — all began their careers as conservative Democrats in the first place before making the logical leap to the GOP at a time when Republicans were beginning to claw back control of states they had lost after Reconstruction.

Crist’s path is more difficult: The man known as “Chain Gang Charlie” during his time as Florida’s Republican attorney general must now convince an increasingly liberal Democratic primary electorate he is one of them, before he gets the chance to convince a broader swath of Florida voters that he should be entrusted with the governorship once again.