MIAMI — In the gilded halls of Donald Trump’s Mar-a-Lago, the former Ukrainian government official blended in with about 400 nattily dressed guests for a Charlie Crist fundraiser, posing for a photo with the candidate for governor.
But the picture of Crist and Volodymyr Shcherban quickly became a sign of unwelcome news because the pro-Russia politician had recently been charged with immigration violations for overstaying his visa — and he was facing a host of corruption and election fraud charges back home.
Crist promptly disavowed any knowledge of Shcherban and his campaign couldn’t explain why he was at the fundraiser.
The year was 2006. And the incident with Shcherban, splashed across the newspapers in the Sunshine State, would be the first instance of Crist’s association with Trump becoming a primary issue.
It wouldn’t be the last.
Now, 16 years later, Trump's shadow again hangs over a Crist gubernatorial primary.
“Anything related to Trump is probably going to hurt Crist in a Democratic primary. That’s just a blanket statement,” said Brad Coker, pollster for Mason-Dixon Polling & Strategy. “Charlie has been such a political chameleon over the years that he’s always vulnerable to attacks like this.”
Crist and Trump are no longer friends or allies. Crist today is a Democrat; back then, he was a Republican and, in between, he was an independent. And Trump has gone from a questionable figure in GOP primary politics to becoming the dominant voice of the Republican Party. The former president is reviled by the Democratic Party, which also despises his protégé, Florida Gov. Ron DeSantis.
Still, the arc of the Crist-Trump political alliance and friendship spans a crucial era in Crist’s political career, when he was at the zenith of his Republican power from 2005 to 2010. That year, he lost a Senate race, ultimately as an independent. He lost another race for governor in 2014 as a Democrat.
Elected to Congress in 2016, Crist faces a Democratic primary opponent for governor who — unlike him — has actually won statewide as a Democrat, Florida Agriculture Commissioner Nikki Fried.
On social media and in private conversations with donors and allies, Fried’s campaign has signaled an effort to open a new, more heated phase of the primary by questioning Crist’s once-warm relationship with Trump — from the time Crist gave him a Florida-shaped birthday cake in 2005 to Crist congratulating Trump via text over his 2016 presidential win, which sent Democrats reeling.
Crist's campaign dismissed any talk of his past Trump friendship harming him now.
“This is nonsense. Charlie is the only candidate for governor who has voted twice to impeach President Trump, and Florida voters know exactly where he stands," press secretary Samantha Ramirez said in an email. "Charlie has always been open with Floridians about his record, and that’s why he’s won three elections to Congress as a proud Democrat in the last five years.”
As for the Trump friendship, the Crist campaign says, the former president was not a toxic figure when Crist began courting him in 2005 as part of his successful GOP bid for governor. Earlier that year, Hillary Clinton attended Trump’s wedding to the then-Melania Knauss.
Crist detailed his exodus from the GOP in a book, "The Party’s Over," and his campaign points out that Republicans ostracized him for embracing Democratic President Barack Obama’s 2009 stimulus plan. Crist was a key Florida surrogate for Obama in his 2012 presidential re-election campaign, and polls have shown that Crist is relatively popular with Black voters, who comprise about 28 percent of the Florida Democratic Party electorate.
Powered by those Black voters, Crist leads Fried 44-27 percent overall, with state Sen. Annette Taddeo in a distant third at 3 percent, according to the latest Mason-Dixon survey of the Florida race conducted last month. Coker and other Florida insiders say Crist’s lead is also heavily rooted in his name identification advantage — one that he acquired by running statewide six times for four different offices with three different party affiliations since 1998.
“If I were trailing in a Democratic primary, I would use Trump,” Coker said.
When Crist ran the last time for governor, in 2014, he faced scant Democratic primary opposition from a little-known and vastly underfunded state senator, Nan Rich.
A website attacking Crist as a Republican in that Democratic primary was not used much in that campaign but remains active today.
Crist went on to lose the 2014 race against then-Gov. Rick Scott, who was re-elected. Scott first won the office in 2010 when Crist decided not to seek re-election as a Republican governor and instead run for Senate. But Crist left the GOP when Marco Rubio threatened to beat him in the primary, and he became an independent and lost that general election, too.
"One day he can be campaigning with Trump, and the next he’s losing to Marco Rubio and then to Rick Scott. He doesn’t stand for anything, and Florida voters won’t stand or lose with him again,” Fried campaign spokesman Keith Edwards said via text message.
Throughout the week, Edwards began using Twitter to criticize Crist's record — an opening salvo in Fried's campaign. Edwards said Crist will not get a “free hall pass” in this primary when compared to 2014. The Florida primary is scheduled for Aug. 23.
But pollster Steve Vancore said he’s not sure if Crist will pay more of a price for once being a Republican because it’s old news.
“He’s been forgiven for being a Republican, and I’m not sure the Trump hit will work,” he said. “But just because Democrats have forgiven Crist doesn’t mean that they’re enthusiastic about him.”
As with the Mason-Dixon survey, Vancore said his own internal polling shows DeSantis in a strong position against any Democratic nominee in Florida, a state Trump won by more than 3 percentage points — a blowout by Sunshine State standards where elections can be decided by a point or less.
Trump’s relationship with Crist began in 2005 when Crist was Florida’s elected attorney general running as a more-moderate Republican candidate, compared to his primary rival.
Trump’s spokesman would not comment for this article.
Trump’s support for Crist was gold for the candidate, who raised millions of dollars at four separate Trump fundraisers at his Palm Beach and New York City properties in the 2006 election cycle. At Trump’s first fundraiser for Crist, held on the birthday of “The Apprentice" star in 2005, Crist presented Trump with a Florida-shaped birthday cake.
At the second Trump fundraiser, at Mar-a-Lago, Crist hit Trump-related turbulence when the former Ukrainian regional governor, Shcherban, inexplicably showed up at the event. A second guest, who was under investigation by Crist’s attorney general’s office at the time, was also in attendance and gave money. Crist’s campaign ultimately returned his money.
Crist’s Republican opponent at the time, Tom Gallagher, criticized the candidate’s relationship with the pro-gambling Trump, noting that “investors like Mr. Trump are always looking for a return.’’
Crist and Trump denied impropriety or any pay-for-play notion.
Trump backed Crist's doomed Senate run in 2010 but he didn't contribute to his 2014 gubernatorial bid as a Democrat.
Unlike the 2010 and the 2014 races, Trump became a campaign issue in Crist’s 2016 congressional campaign, but in a totally unexpected way. At the time, the Crist-backing Democratic Congressional Campaign Committee attacked his Republican rival, Rep. David Jolly, by doctoring a photo to make it appear as if the incumbent congressman had been in a picture with Trump when he never had been.
Adding to the insult for Jolly: He had been ostracized from the Republican Party because he was critical of Trump, while Crist got a pass for his prior association with Trump.
“That was the only race in the country where the Republican had denounced Trump and the Democratic nominee wouldn’t, was soft on him,” Jolly said.
“But politics is politics,” he said. “If there was a relationship between Trump and Charlie to exploit, a skilled Democratic candidate would do that. In 2016, it was still fresh. Today, it’s less so. But it won’t be hard for Nikki Fried to find those quotes and pictures.”
After Crist won the race in 2016, he told Politico that he believed Trump would be "pragmatic," and he said his House Democratic colleagues accepted his political conversion.
"What is the expression? Blessed is the convert,” Crist told the publication. "They’ve treated me very well because, though I used to be a Republican, I saw the light.”